Hotels in Chicago

Hotels in Chicago offer top-class accommodations in a destination nicknamed “The Windy City”. Although literally a windy city, Chicago’s nickname derives from its bloviating politicians. Locally pronounced Chi-caw-go, The Windy City is known for its deep dish pizza, fine restaurants, sports, derivatives exchange, museums, shopping, conventions, architecture, parks, lakefront and neighborhood watering holes. Located in northeastern Illinois along Lake Michigan‘s southwestern shoreline, Chicago’s area covers over 225 square miles. An easily accessible city, Chicago is serviced largely by its “L” train system, which helps provide convenient access to places such as Wrigley Field (Chicago Cubs / concert venue),  Soldier Field (presently – Chicago Bears / concert venue) and Guaranteed Rate Field (Chicago White Sox / concert venue), as well as countless other establishments. When visiting Chicago, keep in mind that winters can be bitter, especially with the wind chill, while summers are pleasant. Downtown Chicago’s Wacker Drive actually has two levels, one above-ground, as well as a more convenient by-pass below-ground. Along Wacker Drive you may find the Chicago River, which is dyed green during Saint Patrick’s Day, as well as some of the most impressive architecture out there. Chicago hallmarks are its movable bascule bridges, which connect downtown to the north side. While Chicago’s downtown and north side areas in particular offer many outstanding places of interest, travel to its farther west and south sides generally is not advisable. A major sports town, Chicago professional teams include the Chicago Bears, Chicago Bulls, Chicago Cubs, Chicago White Sox, Chicago Blackhawks, Chicago Fire and Chicago Sky. Not just a sports city though, Chicago is home to the Art Institute of Chicago, Field Museum of Natural History, Adler Planetarium and Museum of Science and Industry. Encompassing Chicago are thousands of smaller establishments, such as the many museums, art galleries, performing arts theaters, comedy clubs, restaurants and bars referenced below. The southward, downtown Board of Trade area is home to the Chicago Mercantile Exchange, which began trading butter and eggs contracts circa 1898, and has since become the world’s largest options and futures open interest exchange. Close to Navy Pier, Chicago’s “play pen” is the place to be for boat parties. Windy City big events include Lollapalooza, Windy City Smokeout, Taste of Chicago, World Music Festival Chicago, Chicago Jazz Festival, Chicago Blues Festival, Grant Park Music Festival, Pitchfork Music Festival, Riot Fest, North Coast Music Festival, Ravinia Festival, Chicago Gospel Music Festival, Chicago Air and Water Show, Chicago SummerDance, Wicker Park Fest, Hyde Park Jazz Festival, Ruido Fest, NASCAR Chicago Street Race, Rolex United States Sail Grand Prix, LIV Golf Invitational Chicago, C2E2 (Comic Con) and The Bristol Renaissance Faire (Kenosha WI). Hotels in Chicago are some of the Midwest United States’ best. Before we get to hotels in Chicago, let’s take a look at some more background information on the area to help you along the way.

The first known peoples to have inhabited the Chicago area were the Miami and Sauk-and-Fox Native Americans, followed by the Potawatomi in the mid-17th century. Jean Baptiste Point du Sable, regarded as the “Founder of Chicago”, established Chicago’s first known permanent settlement during the 1780s. The Northwest Indian War of 1786 between the United States and Northwestern Confederacy resulted in a United States victory and occupation of the Northwest Territory. Native tribes turned over the Chicago area to the United States military in accordance with the Treaty of Greenville, at which time Fort Dearborn was constructed by the U.S. Army. Fort Dearborn was destroyed and later rebuilt by way of the Battle of Fort Dearborn. In 1833, the Treaty of Chicago sent the Potawatomi west of the Mississippi River. Organized as a town on August 12, 1833, Chicago grew from a population of 200 to over 6,000 people within seven years thereafter. On March 4, 1837, Chicago was incorporated, becoming one of the world’s fastest growing cities for several decades. In 1848, the Chicago Board of Trade formed the world’s first-ever standardized exchange-traded forward contracts, or futures contracts. Once the site of an ancient portage known as the Chicago Portage, the area further developed into an important transportation hub via railway and canal. The “Wigwam”, one of the city’s earliest convention centers, hosted Abraham Lincoln’s 1860 Republican National Convention presidential nomination. In 1871, The Great Chicago Fire resulted in around 300 deaths and $222 million in damages, or around $5.5 billion in present valuation. Following the Great Chicago Fire, steel and stone materials were used to rebuild the city. In 1885, William Le Baron Jenney designed the world’s first skyscraper, known as the Home Insurance Building. The World’s Columbian Exposition, which attracted 27.5 million visitors, was held at present-day Jackson Park in 1893. By 1900, American-born and immigrant Europeans (Germans, Irish, Poles, Swedes, and Czechs) made up around 66% of the city’s population, with whites totaling 98.1% of the overall demographic. Al Capone, in 1919, moved from New York City to Chicago to become  boss of the Chicago Outfit, In 1929, the St. Valentine’s Day Massacre was carried out on the city’s north side. Throughout World War II, Chicago alone produced more steel than the United Kingdom and Nazi Germany.

Today, the Chicagoland area is inhabited by over 10 million people.  The Midwest‘s most populous city, Chicago is home also to the world’s largest derivatives market.  Locally, a diverse economy helped The Windy City generate $689 billion  in GDP circa 2018. Chicago sports legends include George “Papa Bear” Halas, founder and owner of the Chicago Bears who coached for 40 years while winning 8 NFL Championships, Mike Ditka, who coached the Bears’ only Super Bowl win in 1986, Michael Jordan, who led the Chicago Bulls to 6 NBA championships in just 1,072 games, and Bobby Hull, the Chicago Blackhawk legend who scored 610 NHL goals in just 1,063 games. Apart from sports, influential Chicago inhabitants have included Ernest Hemingway, Daniel Burnham, John Wellborn Root, Frank Lloyd Wright, Jane Addams, Milton Friedman, Marshall Field, Cyrus Hall McCormick and George Pullman. Chicago’s climate is humid continental, with pleasant summers and often bitter winters. Additional, major points of interest include Shedd Aquarium, The Museum of Contemporary Art, United Center (Madhouse on Madison), McCormick Place, Millennium Park, Chicago Lakefront Trail, Michigan Avenue and Lincoln Park Zoo. Local foods include deep dish pizza, pizza puffs, Italian beef sandwiches, hot dogs, steak, pork chops, barbecue, Jibarito sandwiches, fried fish, flaming Saganaki and rainbow cone ice cream. Popular drinks are craft beer and wine, while Malört is a bitter, wormwood-based, Swedish schnapps. Now that we have some background information on the area. it’s time for hotels in Chicago that will help make for an unforgettable experience.

 

 

 

Trump International Hotel & Tower Chicago

401 North Wabash Avenue, River North

Hotels in Chicago

Marina City

A 92-story, landmark building of stainless steel and tinted glass, Trump International Hotel & Tower Chicago features stunning city, river and lake views, luxury spa services, fine dining, upscale amenities, floor-to-ceiling windows, spacious rooms, limestone bathrooms, deep-soaking bath tubs, 65-inch flat-screen TVs, a bar, a seasonal outdoor terrace, a 75-foot heated indoor swimming pool surrounded by plush lounge chairs, a fitness center and a business center. Anthony Cristiano | Hair Salon (hair salon), Wendella Tours (boat tour agency), Chicago Water Taxi (ferry service), Ghirardelli Ice Cream & Chocolate Shop (frozen yogurt shop), The Wrigley Building (business center) and more are in the area.

Within feet:

      • Marina City
      • Bridgehouse and Chicago River Museum
      • Chicago Tribune Tower
      • Chicago Vietnam Veterans Memorial

Within 1 mile:

      • Buckingham Memorial Fountain

Within 1.2 miles:

      • Navy Pier

Within 1.6 miles:

      • Field Museum of Natural History

Within 20 miles:

      • Chicago Executive Airport

Trump International Hotel & Tower Chicago is 14 miles from Chicago O’Hare International Airport.

Approximate cost per night (Premier Two-Bedroom Suite): $2,335

Cost per person (six people): $389

 

 

 

Viceroy Chicago

1118 North State Street

Hotels in Chicago

Oak Street Beach

Viceroy Chicago offers a seasonal rooftop pool, a rooftop bar and lounge, panoramic city views, on-site dining, flat-screen TVs, plush lounge seating, free WiFi, fully-stocked mini-bars, coffee machines, a fitness center and an event space. Nearby are Somerset (New American restaurant), Devereaux (bar), Gold Coast – Lou Malnati’s Pizzeria (pizza restaurant), Velvet Taco (taco restaurant), CorePower Yoga (yoga studio), Maple & Ash (steak house), Bistrot Zinc (French restaurant) and more.

Within feet:

      • Oak Street Beach
      • Chicago Lakefront Trail
      • Water Tower Chicago
      • Time Life Building

Within 1.2 miles:

      • Lincoln Park Zoo

Within 1.4 miles:

      • Cloud Gate – The Bean

Within 1.7 miles:

      • Willis Tower

Within 8 miles:

      • Museum of Science and Industry – Chicago

Viceroy Chicago is 14 miles from Chicago O’Hare International Airport.

Approximate cost per night (Suite with Lake View): $1,167

Cost per person (four people): $291

 

 

 

Pendry Chicago

230 North Michigan Avenue, Chicago Loop

Hotels in Chicago

McCormick Bridgehouse and Chicago River Museum

Providing free bikes, private parking, a fitness center, a shared lounge, a restaurant, a bar, a 24-hour front desk, free WiFi, flat-screen TVs, safety deposit boxes, city views, coffee machines, a terrace and a business area, Pendry Chicago can be found near Venteux Brasserie, Cafe & Oyster Bar (French restaurant), Bar Pendry Chicago (bar), Roti (Mediterranean restaurant), Léa (French restaurant), Morton’s The Steakhouse (restaurant) and more.

Within feet:

Within 1.8 miles:

      • North Avenue Beach

Within 25 miles:

      • Four Lakes Rope Tow

Pendry Chicago is 14 miles from Chicago O’Hare International Airport.

Approximate cost per night (Pendry Suite): $2,579

Cost per person (four people): $644

 

 

 

Dr Brandt Skincare

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

500 South Dearborn Street, Chicago Loop

Hotels in Chicago

Millennium Park

Bluegreen Vacations Hotel Blake, Ascend Resort Collection comes with a restaurant, a 24-hour business center, free WiFi, expansive windows, rainfall showerheads and complimentary natural body care products. You’ll find Morton Building (hisorical landmark), Meli Cafe (American restaurant), Gino’s East – South Loop (pizza restaurant), Bespoke Men’s Grooming (hair salon) and more nearby.

Within feet:

      • Millennium Park
      • Harold Washington Library Center
      • Dearborn Station
      • Grant Park

Within 1.3 miles:

      • Adler Planetarium & Astronomy Museum

Within 1.7 miles:

      • 360 Chicago

Within 4 miles:

      • Oakwood Beach

Bluegreen Vacations Hotel Blake, Ascend Resort Collection is 8 miles from Midway International Airport.

Approximate cost per night (Queen Room): $407

Cost per person (four people): $101

 

 

 

SpringHill Suites by Marriott Chicago Chinatown

2357 South Wentworth Avenue

Hotels in Chicago

Chinatown Chicago

Located in Chinatown, SpringHill Suites by Marriott Chicago has a fitness center, private parking, a shared lounge, air conditioning, city views, desks, free WiFi, flat-screen TVs, hairdryers, a breakfast buffet, paid parking, a business center, a snack bar and a 24-hour front desk. Close by are Friends’ BBQ (Chinese restaurant), Happy Lamb Hot Pot (hot pot restaurant), Yummy Yummy Noodles (Chinese restaurant), JM Hair Salon (hair salon) and more.

Within feet:

Within 1 mile:

      • Chicago Lakefront Trail

Within 1.5 miles:

      • Arvey Field

Within 2.1 miles:

      • Art Institute of Chicago

SpringHill Suites by Marriott Chicago is 7 miles from Midway International Airport.

Approximate cost per night (Queen Suite): $198

Cost per person (five people): $39

 

 

 

Kasa Magnificent Mile Chicago

1 W Superior St, River North

Hotels in Chicago

Arts Club of Chicago

Free WiFi, desks, flat-screen TVs, air conditioning and balconies are found at Kasa Magnificent Mile Chicago. Mary Walter Boutique (women’s clothing store), Tzuco (Mexican restaurant), Natural Beauty Med Spa (medical spa), Pause Massage (massage spa), Jack Alexander Salon & Spa 2 (hair salon) and more are within range.

Within feet:

Within 1.1 miles:

      • Art Institute of Chicago

Within 1.3 miles:

      • Navy Pier

Within 4.7 miles:

      • Montrose Beach

Kasa Magnificent Mile Chicago is 14  miles from Chicago O’Hare International Airport.

Approximate cost per night (Two-Bedroom Apartment): $823

Cost per person (five people): $164

 

 

 

Nobu Hotel Chicago

155 North Peoria Street, West Loop

Hotels in Chicago

Willis Tower

Boasting a bar, private parking, a restaurant, a fitness center, an indoor pool, a sauna, a 24-hour front desk, shuttle service, free WiFi and flat-screen TVs, Nobu Hotel Chicago is near Gino & Marty’s (restaurant), Levain Bakery, Bar Siena (Italian restaurant), Leña Brava (Mexican restaurant), Cruz Blanca Brewpub (Mexican restaurant), Jeni’s Splendid Ice Creams (ice cream shop), Velvet Taco (taco restaurant), Bonci Pizzeria (pizza restaurant), KINTON RAMEN (Ramen restaurant) and more.

Within feet:

Within 1 mile:

      • Chase Tower
      • Picasso Statue

Within 1.2 miles:

      • Chicago Vietnam Veterans Memorial

Within 2.1 miles:

      • Field Museum of Natural History

Nobu Hotel Chicago is 8 miles from Midway International Airport.

Approximate cost per night (Suite): $3,726

 

 

 

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The Langham Chicago

330 North Wabash Avenue, River North

Hotels in Chicago

House Of Blues Chicago

Warm tones, darks woods, marble Alaskan white granite bathrooms, deep soaking bath tubs, rainfall shower heads, upscale bath amenities, city views, floor-to-ceiling windows, a spa, a fitness center, a restaurant and afternoon tea compliment The Langham Chicago. Close by are Chuan Spa at The Langham, Gus’s World Famous Fried Chicken, Rossi’s (bar), Radio Room (American restaurant), Museum of Broadcast Communications, SPIN Chicago (restaurant), Yolk – Marina City (brunch restaurant), Chief Chicago Limo (limousine service), North Loop Market (grocery store), Smith & Wollensky (steak house) and more.

Within feet:

Within 1.2 miles:

      • Navy Pier

Within 4 miles:

      • Guaranteed Rate Field

Within 4.4 miles:

      • Wrigley Field

The Langham Chicago is 9.1 miles from Midway International Airport.

Approximate cost per night (one-bedroom suite): $1,169

Cost per person (four people): $292

 

 

 

Hotel Zachary, Chicago, a Tribute Portfolio Hotel

3630 North Clark Street, Lakeview

Hotels in Chicago

Wrigley Field

Across the street from historic Wrigley Field, Hotel Zachary comes with on-site dining, contemporary rooms, free WiFi, natural lighting, floor-to-ceiling windows, 55-inch flat-screen TVs, bathrobes, deluxe bath amenities, hardwood floors, panoramic ballpark and city skyline views, breakfast, a lobby bar and event facilities. Nearby are Mordecai (gastropub), Hush Money (cocktail bar), Clark Street Sports – Wrigleyville (sports memorabilia store), Swift & Sons Tavern & Oyster Bar – Wrigleyville (American restaurant), Alma (cocktail bar), Gallagher Way (park) and more.

Within feet:

Within 1.6 miles:

      • Montrose Beach

Within 1.9 miles:

      • Peggy Notebaert Nature Museum

Within 2 miles:

      • Lincoln Park Conservatory
      • Saddle & Cycle Club

Hotel Zachary is 11 miles from Chicago O’Hare International Airport.

Approximate cost per night (Superior Queen Room): $473

Cost per person (four people): $118

 

 

 

Old Town Two-Bedroom House

1515 North Wells

Hotels in Chicago

Chicago History Museum

Old Town Two-Bedroom House provides 2 bedrooms, 2 bathrooms, air conditioning, a patio, facilities for disabled guests, free WiFi, a flat-screen TV, a washing machine and a fully-equipped kitchen. Salon Vie Rebelle (beauty salon), Orangetheory Fitness (gym), The VIG (restaurant), A Red Orchid Theatre (performing arts theater), Kamehachi (Japanese restaurant), Old Town Oil (gift basket store), La Fournette (bakery), State Street Barbers (barber shop), Kanela Breakfast Club (breakfast restaurant), Gallucci Pizzeria Napoletana (pizza restaurant), Philz Coffee (coffee shop), Art Of Hair Design (beauty salon), Crumbl – Old Town (dessert shop), The Spice House (spice store), Topo Gigio Ristorante (Italian restaurant), Fudge Pot (candy store), Zanies Comedy Night Club (comedy club), Up Down Cigar (tobacco shop), 80 Proof (bar) and more are in the neighborhood.

Within feet:

Within 1.1 miles:

      • Chicago Museum of Contemporary Art

Within 1.2 miles:

      • Peggy Notebaert Nature Museum

Within 2.1 miles:

      • Willis Tower

Old Town Two-Bedroom House is 19 miles from Chicago O’Hare International Airport.

Approximate cost per night: $791

Cost per person (four people): $197

 

 

 

The Peninsula Chicago

108 East Superior, River North

Hotels in Chicago

Water Tower Chicago

Boasting a full-service Asian-inspired spa, an award-winning restaurants, spacious rooms, city views, 42-inch flat-screen TVs, free WiFi, temperature and lighting control consoles, soaking tubs, a half-Olympic indoor swimming pool enclosed by floor-to-ceiling windows, a modern gym, fitness and yoga classes, an outdoor terrace and afternoon tea serving champagne and chocolate, The Peninsula Chicago is near Pierrot Gourmet at The Peninsula (French restaurant), The Peninsula Spa, Shanghai Terrace (Chinese restaurant), Z Bar (bar), Tiffany & Co. (jewelry store), Victoria’s Secret & PINK (lingerie store), RL Restaurant (American restaurant), ALTHEA (vegan restaurant), Friends Sushi (Japanese restaurant), Rosebud on Rush (Italian restaurant), Giordano’s (pizza restaurant) and more.

Within feet:

      • Water Tower Chicago
      • Michigan Avenue
      • Ann & Robert H. Lurie Children’s Hospital of Chicago
      • Northwestern Memorial Hospital

Within 1.4 miles:

      • Union Station

Within 4.5 miles:

      • Guaranteed Rate Field

The Peninsula Chicago is 9.6 miles from Midway International Airport.

Approximate cost per night (deluxe suite): $1,555

Cost per person (five people): $311

 

 

 

Lakeview Stone Mansion

3152 North Pine Grove Avenue, Lakeview

Hotels in Chicago

Fullerton Beach

You’ll get 4 bedrooms, 2 bathrooms, a garden, a tennis court, air conditioning, a patio, a picnic area, free WiFi, free private parking, a terrace, quiet street views, a flat-screen TV, a fully-equipped kitchen, a fireplace and an on-site bar at Lakeview Stone Mansion. Just down the street are  Buena Vista Restaurant (Mexican restaurant), Wilde Bar & Restaurant (bar & grill), Yellowtail Sushi Bar & Asian Kitchen (Japanese restaurant), Fancy Plants Cafe (cafe), Luxura Med Spa Lakeview (spa), Robert Jeffrey Salon (hair salon), DryHop Brewers (brewery), Roebuck (brewpub), Archetype CrossFit (gym), Broadway Liquors (liquor store), RockItCoin Bitcoin ATM, BottlesUp! (wine store), Muse Spirits (bar), Laugh Factory (comedy club), Broadway Shoe Repair (shoe repair shop), Mini Nails (nail salon), Salad House (salad shop), The Nail Collaborative (nail salon), OMI Cafe, Dance On Broadway (dance school), Choc Choc Cosmetics (cosmetics store), Intelligentsia Coffee Broadway Coffeebar (coffee shop), The NOW Massage Lakeview (massage therapist), Sila’s (Mediterranean restaurant), Dong-ne (Korean restaurant), Tom Yum Cafe (Thai restaurant), Fox Training Studio (fitness center), The Bagel Restaurant and Deli (restaurant), Stella’s Diner, Dram Shop (bar) and more.

Within feet:

      • Fullerton Beach
      • Belmont Train Station

Within 1.1 miles:

      • Lincoln Park Conservatory

Within 1.5 miles:

      • Lincoln Park Zoo

Within 2.6 miles:

      • Saddle & Cycle Club

Within 4.6 miles:

      • Buckingham Memorial Fountain

Lakeview Stone Mansion is 12 miles from Chicago O’Hare International Airport.

Approximate cost per night: $1,846

Cost per person (twenty people): $92

 

 

 

The Guesthouse Hotel

4872 North Clark

Hotels in Chicago

Saddle & Cycle Club

With gourmet kitchens, a fitness center, free WiFi, flat-screen TVs, high ceilings, private balconies, washing machines, barbecue facilities, a 24-hour front desk, meeting facilities and a shared lounge, The Guesthouse Hotel is next door to Pick Me Up Cafe (restaurant) and Revive Massage Therapy & MedSpa (massage therapist).

Within feet:

Within 1 mile:

      • Foster Beach

Within 4.4 miles:

      • Wicker Park

Within 4.9 miles:

      • Skokie Northshore Sculpture Park

The Guesthouse Hotel is 11 miles from Chicago O’Hare International Airport.

Approximate cost per night (Three-Bedroom Suite): $498

Cost per person (six people): $83

 

 

 

Wrigleyville Two-Bedroom House

3406 N Seminary Ave, Lakeview

Hotels in Chicago

Addison Subway Station

Just 4 blocks from Wrigley Field, Wrigleyville Two-Bedroom House has 2 bedrooms, 2 bathrooms, air conditioning, a balcony, concierge service, an ATM, free WiFi, a flat-screen TV, a washing machine and a fully-equipped kitchen. You may find Al’s #1 Italian Beef (sandwich shop), Cheba Hut “Toasted” Subs (sandwich shop – bar), Penny’s Noodle Shop (noodle shop), Bolivar & Lincoln (Venezuelan restaurant), Reflexion Spa (massage therapist) and Two Hearted Queen (coffee shop) in the neighborhood.

Within feet:

      • Addison Subway Station
      • Chicago Lakefront Trail

Within 1.7 miles:

      • Peggy Notebaert Nature Museum

Within 2.9 miles:

      • Charnley-Persky House Museum

Within 3.6 miles:

      • Loyola University Museum of Art

Wrigleyville Two-Bedroom House is 11 miles from Midway International Airport.

Approximate cost per night: $202

Cost per person (six people): $33

 

 

 

Old Town Mansion

1509 North Sedgwick Street 3

Hotels in Chicago

Charnley-Persky House Museum

Old Town Mansion has 8 bedrooms, 4 bathrooms, free WiFi, a flat-screen TV, a fully-equipped kitchen and a private entrance. Kapéj Coffee Roasters (coffee shop), Wild Willow Salon (beauty salon), Pazza Pizza (fast food restaurant), European Wax Center (waxing hair removal service), Sweet Vegan Bakes (vegan restaurant) and more are in the area.

Within feet:

Within 1.1 miles:

      • 360 Chicago

Within 3.2 miles:

      • Field Museum of Natural History

Old Town Mansion is 13 miles from Chicago O’Hare International Airport.

Approximate cost per night: $2,430

Cost per person (sixteen people): $151

 

 

 

Xbox Game Pass

Gold Coast Two-Bedroom Apartment

21 East Chestnut Street 7G

Hotels in Chicago

360 Chicago

Offering 2 bedrooms, air conditioning, free WiFi, a flat-screen TV, a washing machine, a fully-equipped kitchen and a fireplace, Gold Coast Two-Bedroom Apartment is near Bistronomic (restaurant), Lamborghini Gold Coast (lamborghini dealer), MASERATI of CHICAGO (maserati dealer), Perillo (car dealer), Devil Dawgs Rush St (hot dog restaurant), Streeter’s Tavern (bar), Angelina’s Psychic Readings (psychic), Trove Smoking Treasures (tobacco shop), Chick-fil-A, Alpana (restaurant), Friends Ramen (Ramen restaurant) and more.

Within feet:

Within 1.1 miles:

      • Cloud Gate – The Bean

Within 1.3 miles:

      • Art Institute of Chicago

Within 2.4 miles:

      • Adler Planetarium & Astronomy Museum

Gold Coast Two-Bedroom Apartment is 14 miles from Chicago O’Hare International Airport.

Approximate cost per night: $413

Cost per person (four people): $103

 

 

 

North Paulina Penthouse

884 North Paulina Street

Hotels in Chicago

Wicker Park

An exceptional penthouse accommodation, North Paulina Penthouse has 3 bedrooms, 2 bathrooms, free WiFi, a flat-screen TV, a washing machine and a fully-equipped kitchen. Forbidden Root Restaurant & Brewery (brewpub), Yuzu Sushi & Robata Grill (sushi restaurant), JJ Thai Street Food (Thai restaurant), Alcala’s Western Wear (western apparel store), Flour Power (restaurant), Anytime Fitness (gym), Beatnik West Town (restaurant), Koko’s Mediterranean Grille (Mediterranean restaurant), Arami (Japanese restaurant), West Town Bakery, Cleos Bar and Grill (sports bar), Hummus Grill Chicago (Mediterranean restaurant), Damen Tavern (bar), Nilda’s Place (bar), Black Dog Gelato (ice cream shop), Kasama (restaurant), Taqueria Traspasada 2 (taco restaurant), Opart Thai House – West Town (Thai restaurant), Provare Chicago (Italian restaurant), Standing Passengers (coffee shop), Beauty Bar Chicago (bar), Five Star Bar (bar), Chipp Inn (bar), Mano Modern Cafe (coffee shop), Market Select (gourmet grocery store), Kimchi Pop by Chef Son (Korean restaurant) and more are in the vicinity.

Within feet:

      • Wicker Park
      • Division Subway Station

Within 2.1 miles:

      • Chicago Riverwalk

Within 2.3 miles:

      • Picasso Statue

Within 2.9 miles:

      • Ohio Street Beach

North Paulina Penthouse is 8 miles from Midway International Airport.

Approximate cost per night: $791

Cost per person (six people): $131

 

 

 

The LaSalle Chicago, Autograph Collection

208 South LaSalle Street, Chicago Loop

Hotels in Chicago

Chase Tower

A fitness center, a shared lounge, a bar, a 24-hour front desk, free WiFi, an ATM, concierge service, luggage storage and a restaurant are amenities at The LaSalle Chicago, Autograph Collection. Grill on 21 (restaurant), The Florentine (Italian restaurant), The Rookery Building (historical place), Elephant & Castle (restaurant), Field Building (historical landmark), Drybar – W Chicago City Center (hair salon) and more are nearby.

Within feet:

      • Chase Tower
      • Willis Tower
      • Art Institute of Chicago
      • Millennium Park

Within 1.2 miles:

      • Field Museum of Natural History

Within 1.4 miles:

      • Ohio Street Beach

The LaSalle Chicago, Autograph Collection is 8 miles from Midway International Airport.

Approximate cost per night (Executive Suite): $949

Cost per person (four people): $237

 

 

 

River North Three-Bedroom Apartment

353 West Chicago Avenue, River North

Hotels in Chicago

Chicago Riverwalk

River North Three-Bedroom Apartment comes with 3 bedrooms, 2 bathrooms, a balcony, free private parking, a fully-equipped kitchen and a fireplace. In the area you may find Lang Ocean Spa Thai Bodywork (Thai massage therapist), GOAT Wellness (health spa), Michael & Michael (hair salon), Ikigai Sushi & Izakaya (authentic Japanese restaurant) and more.

Within feet:

      • Chicago Riverwalk
      • Water Tower Chicago
      • Loyola University Museum of Art
      • Oak Street Beach

Within 1.2 miles:

      • Cloud Gate – The Bean

Within 1.5 miles:

      • Lincoln Park Zoo

River North Three-Bedroom Apartment is 13 miles from Chicago O’Hare International Airport.

Approximate cost per night: $2,380

Cost per person (ten people): $238

 

 

 

Bake Me A Wish

The Penthouse at Grand Plaza

540 North State Street, River North

Where to Stay in Chicago IL

Michigan Avenue

The Penthouse at Grand Plaza offers 3 bedrooms, 3 bathrooms, 3 balconies, a rooftop swimming pool, a sun deck, a fitness center, a basketball court, free WiFi, floor-to-ceiling windows, a fireplace, a fully-equipped kitchen, a dining area and  laundry facilities. It’s close to Bed Bath & Beyond, Cold Stone Creamery, Gelato D’Oro (Italian restaurant), Eggsperience Cafe, M Burger, Osteria Via Stato (Italian restaurant), Weber Grill, The Dinner Detective, Fleming’s Prime Steakhouse, Pizzeria UNO, Broken Shaker (cocktail bar), The Berkshire Room (lounge), Corey’s NYC Bagel Deli, Grossman & Jack Talent and more.

Within feet:

      • Michigan Avenue
      • Shops at Northbridge
      • Chicago Tribune Tower
      • Wrigley Building
      • House Of Blues Chicago

Within 1 mile:

      • Union Station

Within 4.1 miles:

      • Wrigley Field

The Penthouse at Grand Plaza is 9.3 miles from Midway International Airport.

Approximate cost per night (three-bedroom penthouse): $1,587

Cost per person (eight people): $198

 

 

 

Wicker Park Home

1731 West Potomac Avenue Coach House, Wicker Park

Hotels in Chicago

Division Subway Station

Featuring free WiFi, free parking and a garden, Wicker Park Home is in the vicinity of Craft Pizza (pizza restaurant), Tous Les Jours (bakery), Tortello (Italian restaurant), Tailor Barber Co. (barber shop), Wicker Park Fitness (gym), Smoke Daddy BBQ – Wicker Park (barbecue restaurant), Mac’s Wood Grilled (bar & grill), Body High Fitness (fitness center), Yolk – Wicker Park (brunch restaurant), Parlor Pizza Bar (pizza restaurant), Machine: Engineered Dining & Drink (New American restaurant), Sushi Taku (sushi restaurant), CHICAGO BATH HOUSE (day spa), Penelope’s (clothing store), The Perch Kitchen and Tap (restaurant), Easy Bar (bar), Cheba Hut “Toasted” Subs (sandiwch shop), Colectivo Coffee – Wicker Park (coffee shop), Do Division Street Fest (festival), Rainbo Club (dive bar), Takito Kitchen (Mexican restaurant), Benches on Division (art center), Cafe Istanbul (Turkish restaurant), El Bagel Cafe (restaurant), Meraki Room Chicago (hair salon), Bourbon on Division (bar), Innjoy (bar & grill), Jack’s Bistro and Bar (French restaurant), Folklore | Argentine Restaurant (Argentinian restaurant), Le Midi Wine (wine bar), Lash ‘O’ holics (beauty salon), Queen Mary (bar), The Circle Salon (hair salon), Old Dog Barbershop (barber shop), Letizia’s Natural Bakery (bakery), Viktoria Spa (day spa), Holy Trinity Orthodox Cathedral (Eastern Orthodox church), The Inner Town Pub (bar), Wake N Bakery Wicker Park (coffee shop), Philz Coffee (coffee shop), SpaDerma (medical spa), Kurimu (ice cream shop), La Costa West Town (Mexican restaurant), Lawn Craft Hamburger (hamburger restaurant), Bodywise Spa (massage therapist), Dusty Groove (record store), Podhalanka (Polish restaurant), Brazilian Waxing Co (waxing hair removal service), Gorilla Sushi Wicker Park (sushi restaurant), Iron Age Korean Steakhouse (restaurant), Luxo Nail Spa (nail salon), Innovative MedSpa (medical spa), BANG! Salon (hair salon), Grooming Lounge Chicago (barber shop), Shuga Records (record store), Cinnaholic (bakery), Chengdu Impression (Sichuan restaurant), Big Mini Putt Club (miniature golf course), Belmont Army Surplus Wicker Park (Army & navy surplus shop), Komorebi Sushi (sushi restaurant), Falafel & Grill (Middle Eastern restaurant), The Den Theatre (performing arts theater), David Leonardis Gallery (art gallery), Garfield’s Beverage Express (wine store), Shabu Plus Rotary (hot pot restaurant), TITLE Boxing Club Chicago Wicker Park (boxing gym), Antique Taco Wicker Park (taco restaurant), Emporium Arcade Bar (bar), Cracked on Milwaukee (restaurant), Reckless Records (record store), Oiistar (Ramen restaurant) and more.

Within feet:

      • Division Subway Station
      • Wicker Park

Within 2.3 miles:

      • Charnley-Persky House Museum

Within 2.4 miles:

      • Peggy Notebaert Nature Museum

Within 23 miles:

      • Four Lakes Rope Tow

Wicker Park Home is 11 miles from Chicago O’Hare International Airport.

Approximate cost per night: $370

Cost per person (six people): $61

 

 

 

United Center House

2130 West Washington Boulevard

Hotels in Chicago

United Center

Just 2 blocks from the Chicago Bulls and Chicago Blackhawks arena, United Center House provides 4 bedrooms, 4 bathrooms, a garden, a terrace, free private parking, free WiFi, a flat-screen TV, a washing machine, a fully-equipped kitchen, a fireplace and a rooftop barbecue area. Not far also are Midwest Coast Brewing Company (brewery), Walden (event venue), City View Loft (event venue), Sliced | Chicago Charcuterie, Fairlie (event venue), Ovation Chicago (event venue), Coalition Strength & Conditioning (gym), Hovet Fashion Studio (fashion design school), Rhine Hall Distillery (bar), Metric (coffee shop), Brite Donuts & Baked Goods (bakery), The Carter Chicago (event venue), Le Petit Sucre Ltd (bakery), Lil’ Kickers & Skills Institute (soccer club) and more.

Within feet:

Within 1.7 miles:

      • Wicker Park

Within 2.3 miles:

      • Willis Tower

Within 2.7 miles:

      • Marina City
      • Dearborn Station

United Center House is 7 miles from Midway International Airport.

Approximate cost per night: $1,682

Cost per person (sixteen people): $105

 

 

 

The Publishing House Bed and Breakfast

108 North May Street, West Loop

Hotels in Chicago

University of Illinois at Chicago

The Publishing House Bed and Breakfast features free WiFi, a restaurant, a bar, a shared lounge, a buffet breakfast and a business center. Near here you may find The Press Room (American restaurant), Gioia Ristorante e Pastificio (restaurant), Eat Me Milk Me Coffee & Tea (coffee shop), Free People (women’s clothing store), Alice In Ivory (bridal shop), Nancy’s Pizzeria (pizza restaurant), Pockets Restaurant, Monteverde Restaurant & Pastificio (Italian restaurant), Jet’s Pizza, CrossTown Fitness, Cone Gourmet Ice Cream, Black Barrel Tavern, SpaDerma (medical spa), StretchLab (fitness center), Chicago Waffles (brunch restaurant), Cat & Mouse Games (toy store), The CrossRoads Bar & Grill, Sumu Tokyo (sushi restaurant), Third Rail Tavern (bar), Eyelashes R Us (beauty salon) and more.

Within feet:

Within 1 mile:

      • Civic Opera House

Within 1.3 miles:

      • Chicago Board of Trade Building

Within 1.5 miles:

      • DePaul University

The Publishing House Bed and Breakfast is 14.3 miles from Chicago O’Hare International Airport.

Approximate cost per night (Sinclair room): $388

 

 

 

Sol Sana AU

Wrigleyville Gem

3824 North Clark Street, Lakeview

Hotels in Chicago

Sheridan Subway Station

Just up the street from Wrigley Field, Wrigleyville Gem has 3 bedrooms, 2 bathrooms, free WiFi, private parking, air conditioning and a fully-equipped kitchen. Close by are Nuts on Clark (popcorn store), East Lake View Food & Liquor (beer store), Greenstar Brewery (brewery), Hilltop Yoga (yoga studio), Almost Home Tavern & Grill (bar & grill), Cloud Cookie (cookie shop) and more.

Within feet:

      • Sheridan Subway Station
      • Chicago Lakefront Trail

Within 1.7 miles:

      • Saddle & Cycle Club

Within 2.3 miles:

      • Lincoln Park Conservatory

Within 5 miles:

      • Navy Pier

Wrigleyville Gem is 11 miles from Chicago O’Hare International Airport.

Approximate cost per night: $979

Cost per person (seven people): $139

 

 

 

Wrigley Oasis

1207 West Eddy Street, Lakeview

Hotels in Chicago

Southport Subway Station

Also close to Wrigley Field, Wrigley Oasis comes with 3 bedrooms, free WiFi, a flat-screen TV, a patio, a terrace, air conditioning, a fully-equipped kitchen, a coffee machine and a hairdryer. Guthries Tavern (bar) is in the neighborhood.

Within feet:

      • Southport Subway Station

Within 1.7 miles:

      • Montrose Beach

Within 1.8 miles:

      • Fullerton Beach

Within 3.7 miles:

      • 360 Chicago

Wrigley Oasis is 11 miles from Chicago O’Hare International Airport.

Approximate cost per night: $356

Cost per person (six people): $59

 

 

 

McCormick Place Apartment

2036 South Michigan Avenue, South Loop

Hotels in Chicago

Soldier Field

Near Soldier Field and McCormick Place Convention Center, McCormick Place Apartment has 3 bedrooms, 2 bathrooms, an elevator, full-day security, free WiFi, air conditioning, a fully-equipped kitchen, a coffee machine and a hair dryer. Also nearby are L+A Healing Studio (massage therapist), C.I.T.Y. Club Gymnastics Academy (gymnastics center), Il Culaccino (Italian restaurant), Orangetheory Fitness (gym), Steve’s Bite (Halal restaurant), Mae District (event venue), Reggies Chicago (bar & grill), Momentum Coffee (coffee shop), Phenomenal Fitness (gym) and more.

Within feet:

Within 1 mile:

      • Arvey Field

Within 1.2 miles:

      • Upper Hutchinson Field
      • Adler Planetarium & Astronomy Museum
      • Dearborn Station

Within 2.9 miles:

      • Chicago Museum of Contemporary Art

McCormick Place Apartment is 7 miles from Midway International Airport.

Approximate cost per night: $965

Cost per person (six people): $160

 

 

 

Move With US USA

North Frontier Villa

1149 North Frontier Avenue

Hotels in Chicago

North/Clybourn Subway Station

North Frontier Villa provides 5 bedrooms, 4 bathrooms, free private parking, a balcony, free WiFi, outdoor dining, a terrace, garden views, a flat-screen TV, a fully-equipped kitchen, air conditioning, a washing machine and a hair dryer. In proximity are Old Town Fit Body Forever (fitness center), Chicago Executive Limousine Inc. (transportation service), Chicago Strength (gym), Texican (Mexican restaurant), Bettie’s Chicago (cooking class) and more.

Within feet:

      • North/Clybourn Subway Station
      • Chicago History Museum

Within 1 mile:

      • Charnley-Persky House Museum

Within 1.1 miles:

      • Oak Street Beach

Within 2.3 miles:

      • Buckingham Memorial Fountain

North Frontier Villa is 13 miles from Chicago O’Hare International Airport.

Approximate cost per night (): $1,489

Cost per person (fourteen people): $106

 

 

 

The Rainbow by Cloud9

730 North Milwaukee Avenue, River West

Hotels in Chicago

Chicago Subway Station

Home to multiple, exceptional penthouses, The Rainbow by Cloud9 has a garden, a terrace, free WiFi, private parking, washing machines, fully-equipped kitchens, expansive views, balconies and air conditioning. Gallery Café 2 (coffee shop), Intuit: The Center for Intuitive and Outsider Art (art museum), Tiki Tiki Chicago (tiki bar), Matchbox Bar (bar), Orangetheory Fitness (gym) and more share the area.

Within feet:

      • Chicago Subway Station

Within 1.4 miles:

      • Marina City

Within 1.5 miles:

      • Loyola University Museum of Art

Within 1.8 miles:

      • Millennium Park

The Rainbow by Cloud9 is 13 miles from Chicago O’Hare International Airport.

Approximate cost per night (Penthouse Apartment): $2,178

Cost per person (seven people): $311

 

 

 

Gold Coast Villa

113 West Elm Street, Gold Coast

Hotels in Chicago

North Avenue Beach

You’ll have access to 4 bedrooms, 4 bathrooms, free parking, a garden, free WiFi, a balcony, a terrace, inner courtyard views, a flat-screen TV, a fully-equipped kitchen, air conditioning, a washing machine, a hair dryer, a private entrance and full-day security at Gold Coast Villa. Church of the Ascension (Episcopal church), LaSalle Street Church (Christian church), Dancing Fingers Authentic Chinese Massage (massage spa), Blue Door Kitchen & Garden, BIGGS Mansion Chicago (cigar shop), La Storia, Italian Restaurant, Chicago Q (barbecue restaurant), The Balancing Center (chiropractor) and more are in the area.

Within feet:

      • North Avenue Beach
      • 360 Chicago
      • Chicago History Museum

Within 1.6 miles:

      • Navy Pier

Within 2.8 miles:

      • Adler Planetarium & Astronomy Museum

Gold Coast Villa is 13 miles from Chicago O’Hare International Airport.

Approximate cost per night: $1,501

Cost per person (ten people): $150

 

 

 

ENGRAVABLE STETHOSCOPES - MDF Instruments

West Chicago Avenue Penthouse

2048 West Chicago Avenue, Ukrainian Village

Hotels in Chicago

Ukrainian National Museum

Offering 4 bedrooms, 2 bathrooms, a terrace, free private parking, free WiFi, a flat-screen TV, a washing machine, a fully-equipped kitchen, a private entrance and a furnished rooftop, West Chicago Avenue Penthouse is near North Paulina Penthouse.

Within feet:

Within 2.8 miles:

      • Water Tower Chicago

Within 2.9 miles:

      • Oak Street Beach

Within 3.1 miles:

      • Art Institute of Chicago

West Chicago Avenue Penthouse is 11 miles from Chicago O’Hare International Airport.

Approximate cost per night: $715

Cost per person (ten people): $71

 

 

 

McCormick Place Three-Bedroom Apartment

2036 South Michigan Avenue, South Loop

Hotels in Chicago

Glessner House Museum

Featuring 3 bedrooms, 2 bathrooms, free WiFi, private parking, an elevator, full-day security, air conditioning, a flat-screen TV, a fully-equipped kitchen and a washing machine, McCormick Place Three-Bedroom Apartment is near McCormick Place Apartment.

Within feet:

Within 1.2 miles:

      • Adler Planetarium & Astronomy Museum

Within 1.5 miles:

      • Buckingham Memorial Fountain

Within 2.8 miles:

      • Navy Pier

McCormick Place Three-Bedroom Apartment is 7 miles from Midway International Airport.

Approximate cost per night: $965

Cost per person (six people): $150

 

 

Elvis & Kresse

Urban Mansion

1629 West Superior Street, West Town

Hotels in Chicago

Snowberry Park

Urban Mansion has 5 bedrooms, 4 bathrooms, a garden, free private parking, a fully-equipped kitchen, a sun terrace, a steam room, free WiFi, a flat-screen TV, a washing machine, a fireplace, a game console, laundry service, a snack bar, a bar, a lounge and a rooftop basketball (half) court. Near here are West Chicago Avenue Penthouse and North Paulina Penthouse.

Within feet:

Within 1 mile:

      • Wicker Park

Within 2 miles:

      • Chicago Riverwalk
      • Willis Tower

Within 2.2 miles:

      • Picasso Statue

Within 3.3 miles:

      • Navy Pier

Urban Mansion is 12 miles from  Chicago O’Hare International Airport.

Approximate cost per night: $1,681

Cost per person (ten people): $168

 

 

 

Wicker Park House

1328 North Leavitt Street, Wicker Park

Hotels in Chicago

Damen Subway Station

With 4 bedrooms, 4 bathrooms, air conditioning, free WiFi, a flat-screen TV, a washing machine, a fully-equipped kitchen, a fireplace and a garden, Wicker Park House is in the vicinity of Wicker Park Home.

Within feet:

      • Damen Subway Station
      • Wicker Park

Within 2.5 miles:

      • Lincoln Park Zoo

Within 2.9 miles:

      • Chicago Lakefront Trail

Within 10 miles:

      • Museum of Science and Industry – Chicago

Wicker Park House is 8 miles from Midway International Airport.

Approximate cost per night: $3,540

Cost per person (twenty people): $177

 

 

 

SodaStream USA, inc

Wrigleyville Penthouse

3505 North Seminary Avenue, Lakeview

Hotels in Chicago

Merkle’s Bar & Grill

Steps from Wrigley Field, Wrigleyville Penthouse has 3 bedrooms, 2 bathrooms, air conditioning, a balcony, free WiFi, a flat-screen TV, a washing machine, a fully-equipped kitchen and a private roof deck. Sunnyside Cannabis Dispensary – Wrigleyville (cannabis store), Nude Dude Food Pizza (pizza restaurant), Shake Shack Wrigleyville, Alamo Drafthouse Wrigleyville (movie theater), STRETCH BAR/GRILL (bar & grill), nola bar & kitchen (bar), The Sandlot Wrigley (bar), The Rabbit Hole Wrigley (restaurant), Roadhouse 66 Gas N’ Grill (bar), Lucky’s Sandwich Co. (sandwich shop), Dimo’s Pizza Wrigley (pizza restaurant), Cozy Noodle (Thai restaurant), Happy Camper Pizza – Wrigleyville (pizza restaurant), The Graystone Tavern (bar), Nisei Lounge (bar), W Hair Room Wrigley (barber shop), Rice’N Bread (Korean restaurant), The Newport Theater (performing arts theater), Smoothie joint (juice shop) and more are down the street.

Within feet:

Within 1.7 miles:

      • Peggy Notebaert Nature Museum

Within 2.2 miles:

      • Foster Beach

Within 4.7 miles:

      • Willis Tower

Wrigleyville Penthouse is 11 miles from Chicago O’Hare International Airport.

Approximate cost per night: $788

Cost per person (eight people): $98

 

 

 

Old Town Townhome

1734 N. Sedgwick St., Old Town

Hotels in Chicago

Lincoln Park Conservatory

Offering air conditioning, free WiFi, a flat-screen TV, a fully-equipped kitchen and a fireplace, Old Town Townhome is near Marge’s Still (tavern), Midwest Buddhist Temple (Buddhist temple) and Twin Anchors Restaurant & Tavern (barbecue restaurant).

Within feet:

Within 1.7 miles:

      • Arts Club of Chicago

Within 2.3 miles:

      • Navy Pier

Within 2.5 miles:

      • Art Institute of Chicago

Old Town Townhome is 13 miles from Chicago O’Hare International Airport.

Approximate cost per night: $241

Cost per person (four people): $60

 

 

 

Master & Dynamic MW75 Active Noise-Cancelling Wireless Headphones

The Twin Lions

1919 North Wolcott Avenue, Bucktown

Hotels in Chicago

Clybourn Train Station

The Twin Lions includes 3 bedrooms, a garden, a bar, concierge service, private check-in/out, free WiFi, an outdoor fireplace, air conditioning, a fully-equipped kitchen, a coffee machine, bathrobes, a private entrance, a dart board and a sun terrace.  Lottie’s Pub (bar), En Hakkore Bibimbap & Taco (Korean restaurant), George’s Hot Dogs (fast food restaurant), JuiceRx (juice shop), Mercedes Brow Bar (waxing hair removal service), Le Bouchon (French restaurant), Studio I-90 (beauty salon), Dance with Miss Priya (dance school), St Mary Of The Angels Catholic Church (Catholic church) and more are nearby.

Within feet:

      • Clybourn Train Station

Within 2.3 miles:

      • Chicago History Museum

Within 2.9 miles:

      • 360 Chicago

Within 4 miles:

      • Buckingham Memorial Fountain

The Twin Lions is 9 miles from Midway International Airport.

Approximate cost per night: $393

Cost per person (six people): $60

 

 

 

The Luxury Closet

The Wrigleyville VIP

3618 North Racine Avenue, Lakeview

Hotels in Chicago

Holy Trinity Lutheran Church

A block away from Wrigley Field, The Wrigleyville VIP has 2 bedrooms, 2 bathrooms, air conditioning, a fully-equipped kitchen, a coffee machine, a flat-screen TV and a barbecue. Wrigley Oasis is also in the neighborhood.

Within feet:

Within 2.4 miles:

      • Lincoln Park Zoo

Within 3.9 miles:

      • Water Tower Chicago

The Wrigleyville VIP is 11 miles from Chicago O’Hare International Airport.

Approximate cost per night: $422

Cost per person (eight people): $52

 

 

 

Certified Piedmontese
 

 

So there they are, hotels in Chicago that will help make for a memorable experience. We hope you have found this information valuable and most of all, that you enjoy your time in Illinois!

56 Replies to “Hotels in Chicago”

  1. Your list of Chicago penthouses and Chicago area attractions is amazing. I love the crisp photos, they make me feel there already. I am imagining the club life and fine dining, the music, and the atmosphere. Most of those Penthouses look expensive so they are probably not in my current budget but let’s see what a year brings.

    1. Hi Andy. Thank you for the comment! Chicago has some of the best club life, fine dining, music and atmosphere, so you’re right in the money there. Best luck to you this year. You can do it and the sky’s the limit!

  2. I love Chi-town. As someone who’s only lived on the coasts (born and raised in CA and lived in NY for the past 35 years) Chicago was off my radar. When our daughter moved there for a job opportunity after graduation from college I’ve been able to spend some time in the Windy City. Mt husband and I both love Chicago – the fact that the people are super-friendly plus the amazing restaurants and night life.   In checking some of the prices of the rooms listed they seemed almost too good to be true. Which of these have you personally visited?

    1. Hi lynnsamuelson and thank you for the comments! These listings are based mostly on overall consumer sentiment. Hope you are your husband get to visit some of these amazing stays 🙂

  3. FieldHouse Jones looks really nice for a hangout, I can imagine myself there already! Looks like a super cool for a hangout with friends on my trip, I looked through the other rooms and they are all super sporty looking, awesome! Kinda brings me back to the old high school days, fret bois unite!

  4. Oh wow!!

    I have been to Chicago before but only on a flying visit for a friends wedding. Randolph Street (the first one) is absolutely stunning! I defo want to stay here if we are ever in Chicago again. 

    It looks like something from a movie or Suits!

    Which one is your favourite here?

    Mike

    1. Hi Mike and thanks again! All these Chicago options are truly special, but what do you think about the first one?

  5. Just took a look at the New York rentals, but I must say the Chicago ones look even better. Looks like I will have to plan a round trip. I didn’t realize there were such stunning views in Chicago.

    I love that you have given all the nearest highlights to go and see so that we can pick the penthouse closest to our interests. I would not have a vehicle if I visited Chicago, so I would preferably go for one of the apartments that are near to public transport like the one on Randolph street.

    1. Hi Michel and thank you again for your kind comments. One of the best things about Chicago is that public transportation is easy to come by, so you shouldn’t have any issues with any of these locations. 

  6. This article is so helpful when traveling to Chicago which I do travel there a lot! It’s so nice to know what places are close by and how long it will take to get there. In the past when traveling it was so hard to find out what places was around me. Now I can just go to this site and find the places around me. I can see what dining places are around and what activities I can do and even how long it will take to get there. This site is amazing!

    1. Hi Ruth, thank you so much! All of the references are of the highest caliber, so you are sure to have the best experience at one, or many, of them wherever you stay. Hope to see you again soon!

  7. Thank you for your recommendations for these penthouses. This is a really useful article for a traveller who wishes to travel and stay in Chicago. I like travelling a lot and would love to explore Chicago city someday. Thank you for describing each penthouse description, location and features of these. I should say these are very cosy penthouses. Thanks for the article. 

  8. Hi, 

    Great domain. It’s very catchy. Great post also. I’ve never been to Chicago but a lot of these places look very nice. I especially like The Penthouse at Grand Plaza. It looks very upper class and ritzy. I also like the Sunny Penthouse. I can see myself visiting a lot of those restaurants.

    Have you ever been to any of these places? 

    Brian

  9. i visited your site and i need to ask you this. Is this your first website?, if its not then my word you’ve done a darn good job, your site is very informative, narrative i can safely say this is a good website….the only thing i realize is that a lot of words are under line. Is there any specific reason for this? but all in all keep up the good work. 

    1. Hi Sherman thank you. The underlined words are links to local top-rated businesses. This gives you some ideas for near where you’re staying and easy access to the websites.

  10. It is funny I can across this article because I have been planning a trip to Chicago for a long time and it is about time I make it happen. These penthouses are definitely something different than just renting a hotel room but they are pretty steep for someone who is just going themselves or bringing their family. I guess if you are taking a trip with a group of friends or colleagues then the price per person isn’t so bad when you figure a small hotel room cost about 125 or more a night!

    The triple bunk bed at the Fieldhouse Jones is pretty cool… Never seen a triple bunk bed and the $341 price is a little more reasonable. This is a great reference for where to stay when taking a trip to Chicago and I will definitely bookmark. Have any guides on where to eat, good attractions or entertainment?

    1. Hi Salvatore and thank you! Fieldhouse Jones is definitely a solid option. Some great places around here include BIG & little’s Restaurant, Steven Deer Salon, Millennial Mart, MarwenKiki’s Bistro(French Restaurant), Savage Smyth (event venue), Revitalab (spa and health club), Mogadishu Restaurant, Bismilahi Restaurant, Flex Pilates ChicagoHaute Living (furniture store), Headquarters Beercade (bar & grill), Good Measure (bar), Farmhouse Chicago (American restaurant), Steves Place (American restaurant), Paper Source (stationery store), Griddle 24 (diner), KC Chocolatier (chocolate artisan).

  11. I think the New Reserve Penthouse Collection at 25 West Randolph Street is actually super affordable for 10 people, that’s like the perfect getaway for my team! Tavern’s near, and so is the theatre and shopping places. It’s some ways to the airport but that’s no bother because once we’re there, it’s like the centre of everything we need to have a good time.

    Would be a great place to do a mini team meeting there with the free wifi! With such an attractive offer, no doubt a lot of people are eyeing there as well. How many days in advance would you advise me to book if I were to stay there?

  12. I always see Chicago with a lot of Skyscrapers from all the TV series I’ve seen. All the penthouses you suggested look marvellous and expensive. I guess it’s better to choose one of these rather than hotels because it offers more spectacular views, comfort and style. I assume the unit is much bigger too which is suitable for family or groups. as a tourist, I would probably opt for a place near a museum, park or zoo. Hopefully I can find one of those picture perfect pent houses you suggested. It’s a good option if you are looking for a high end looking but peaceful place to stay. Thanks for sharing!

  13. I like that one that has a lake view and the cost is good too. The cost per person is just $93 so it fits our group’s budget. We are a group of network marketers who will be attending training with our upline living in Chicago. It might take us a week before we’re done with the training. 

    There’s just one thing that I’d like to clarify. The cost is $93 per person, right? What about if I invite a relative who’s living in Chicago to visit us? Are visitors allowed or do we have to pay an extra for a visitor?

    1. Hi Gomer thank you! Visitors should be allowed, but be sure to include how many are actually staying so that you can receive the appropriate number of keys.

  14. whoah! you got some nice photos of the penthouses! I’ve never been to Chicago, and I can’t wait to visit this City hopefully by next year! I’m more like an AirBnB person and I think living in a penthouse in Chicago with a nice view of sky scrapers would be the best way to do it. You pretty much covered everything here, I like the Gorgeous Penthouse with Lake View because of its simplicity and the…. rate.. 🙂

  15. whoah! you got some nice photos of the penthouses! I’ve never been to Chicago, and I can’t wait to visit this City hopefully by next year! I’m more like an AirBnB person and I think living in a penthouse in Chicago with a nice view of sky scrapers would be the best way to do it. You pretty much covered everything here, I like the Gorgeous Penthouse with Lake View because of its simplicity and the…. rate..

  16. Grew up in Iowa, right next to Illinois. 

    Watched the Bears, White Sox, Cubs on TV growing up. Black Hawks are usually contenders. Love UNO Chicago-style Pizza.

    Interviewed for a job there once with Hewitt and Associates. Wasn’t a fit. 

    It’s cold there, but these Penthouse accomodations could make that all right. Lake, night life, music scene, and the food all make Chicago a great destination. I never thought about taking a bunch of people there and rent a Penthouse, which reduces the cost per person to doable levels. And who doesn’t love a little luxury? Great idea.

    This is great idea for visiting any city. I’m going to check out New Orleans. Last time I stayed in the Quarter. Done that once.

    Thanks for this post.

    Mike

    1. Thank you for your experience and insights Mike. The Soldier Field area is really beautiful, perfect place to catch a Bears’ game for anyone who hasn’t tried it yet. If you’re catching a Bears’ game Printers Penthouse might be a good bet. New Orleans sounds fun as well. Happy travels 🙂

  17. Wow, these are some beautiful Penthouses. This would be great for a family from 4-10 people.

    Some are a bit pricy, but for the wonderful view and area, it should be worth it. And I know at these kinds of places you have to book in advance. There is no way around it. I made that mistake once of not booking in advance.

    Thank you for sharing these amazing places and all the best.

    1. Booking in advance is good advice, Aabidah. Generally you should give yourself 30 days to book one of these penthouses, give or take. We’ll let you know if a place is in particularly high demand in the post. Thanks again for stopping by and happy travels out there 🙂

  18. It’s funny how you divide the price by 6, 8 or 10: do owners really let big groups of college kids trash their pricey penthouses for a wild rave?? Perhaps they do and have the insurance policies to back it up?!

    But I do very much appreciate your penthouse reviews. I travel a lot for work and leisure, and I have a conference coming up in Chicago. Sometimes it’s really the most convenient to book just the conference main hotel, since this minimizes the walking, but since I’ve been to Chicago many times, I’m curious about trying something very different. I really liked several of your listings. 

    I wish though you’ve had them on a map, it would really help with the choice.

    1. Hi Phil, pricing is divided by the number of guests who can stay. Pricing accounts for any additional fees and includes a cancellation option. As for college kids, unsure, but we hope that all guests will respect the property. Your suggestion is noted and thank you for stopping by.

  19. Chicago, a city of luxury and beauty. Definitely I am not too surprised with the list of the penthouses made available here. This is a city hub of commerce and definitely, if there were ever to be a reason to have a shot or documentary in this city, a penthouse would be the most ideal to have the feeling of luxury and to accommodate all the crew members. The pricing is very affordable when being shared among the number of people that would stay inside. I like the Reserve Collection Penthouse the most.

    1. Tracy thank you for the comments. Chicago is a beautiful city for sure and your idea of a documentary is an interesting one. Happy travels to you!

  20. What a plethora of information and need. Beautiful photos that make me feel like I am there already. Then description of what is around the penthouses and pricing is really all one needs to book it. This is a wonderful need for a great portion of people and you are providing the solution. Great job

  21. Thanks for this informative article, choosing the type of home you want to live in is one of life’s most complicated tasks, you have made it easier to make a choice, both countryside and city views of a penthouse are truly unique. A perspective that will allow you to enjoy the views. From the picturesque mountains to a city skyline, not to mention the natural and magical views that a penthouse on the beach can have. I’m looking forward in renting one for the holidays for a perfect getaway. Thanks alot 

  22. Wow, what a beautiful collection of penthouse rentals in the Chicago area. I like how you’ve already done the math to figure out how much it would cost per person based on the number of occupants the penthouse can hold. This looks like a great way to enjoy a big event with friends like a bachelor or bachelorette party group… and would also be much less expensive than a trip to Vegas!

  23. Your list of Chicago penthouses and Chicago area attractions is amazing. 

    I love the crisp photos, they make me feel there already. 

    I am imagining the club life and fine dining, the music, and the atmosphere. 

    Most of those Penthouses look expensive so they are probably not in my current budget but let’s see what a year brings.

  24. Oh my,this is nothing but beautiful to see that there are very awesome places here that I can stay in and still enjoy in Chicago. What you have mentioned here about the city, I did not know about before. This is very good and I will be very glad to learn more about it. I like the idea of the different pent houses. They are nice. I will check in whenever I visit to the 21 East Bellevue Place

  25. I  and a couple of friends are thinking of visiting the beautiful state of Chicago this Christmas because we feel like it is going to be a very good experience that will mark one of the best for us this holiday. I am very happy with the fact that you have mentioned that there are a number of penthouses here for me to have fun in. This is just beautiful. I will show this them surely, thanks

  26. Hey, I enjoy a lot while reading your guide on Chicago. I always see Chicago with a lot of Skyscrapers from all the TV series I’ve seen. All the penthouses you suggested look marvellous and expensive. I’m more like an AirBnB person and I think living in a penthouse in Chicago with a nice view of sky scrapers would be the best way to do it. This is great idea for visiting any city. Thanks for sharing. 

    1. Hello Prithvi, Chicago has one of the more impressive skylines out there, especially when it comes to the Midwest US. Chicago IL hotels especially in regard to penthouses are a nice way to stay. Summertime is particularly outstanding in The Windy City. Thanks for stopping by and happy travels!

  27. I think if I were to stay in Chicago, the only thing I can really think of is watching the Chicago Bulls since I love NBA. Sorry if I’ll sound lazy here, but which penthouse is nearest to the basketball arena? Also, I might try eating in some restaurants when I stay in the place. Is there a particular area that you’ve experienced firsthand and you’d strongly recommend?

    1. Hi Dominic. The Madhouse on Madison where the Bulls play is as electric a stadium as any you’ll find out there, so that would be a great place to add to your Chicago trip. The United Center (aka The Madhouse on Madison) is on the downtown area’s west side. The closest from our list of Chicago IL hotels would be Architectural Loop Penthouse, which is only a 10 minute ride via public transport on the 20 bus, for reference.

  28. Hey nice article you have there. Chicago is indeed one of a kind with so much to explore. The Lincoln Park Zoo really got my attention the most with it’s excellent features. It has exactly what my family needs in a suit to be comfortable, like the garden, gymnasium, bicycling etc. This will definitely be the perfect place for us to go during the Summer holiday.

    1. Hi there and thanks for the comments. Lincoln Park Zoo is a great time for the whole family and the best part is, admission is free! Chicago IL hotels are outstanding especially in summertime, and hopefully you get to travel soon.

  29. Thank you for this timely review, Easter holiday is at hand and traveling is one of those ways I enjoy my holiday. The penthouse at grand plaza is a home from home. The spacious amenities from the roof top swimming pool, to the 3 balconies, to the bedroom and other amenities looks like an environment that one should spend some quality time. Top of it are other places around it that one can see

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