Hotels in Chicago


Hotels in Chicago offer top-class accommodations in a locale nicknamed “The Windy City”. Known for its deep dish pizza, its sports, its museums, its shopping, its conventions, its architecture, its parks and its captivating lakefront, Chicago is one of the best cities to visit especially during the summer. Some of Chicago’s most influential people have included Frank Lloyd Wright, Jane Addams, Ernest Hemingway, Carl Sandburg, Marshall Field, and Al Capone. When visiting Chicago, keep in mind that it is indeed a windy city, that the Red Line subway and elevated train will connect you directly to the Chicago Cub’s and Chicago White Sox’s stadiums, and that the south and west sides are generally best avoided. One of the best cities to enjoy an outdoor festival, Chicago is home to events such as Lollapalooza. Indeed, hotels in Chicago are some of the best you’ll find in the Midwest United States. Before we get to hotels in Chicago, let’s take a look at some background information on the area to help you along the way.

Organized as a town on August 12, 1833, Chicago grew from a population of 200 to over 6,000 people in a matter of seven years. Having been incorporated on March 4, 1837, Chicago became one of the world’s fastest growing cities for several of the following decades. In 1848, the Chicago Board of Trade formed the world’s first-ever standardized exchange-traded forward contracts, or futures contracts. One of The Windy City’s earliest convention centers was the Wigwam, which hosted Abraham Lincoln’s 1860 Republican National Convention presidential nomination. The Great Chicago Fire of 1871 caused city rebuilding by way of steel and stone materials. In 1885, Chicago constructed the world’s first skyscraper, known as the Home Insurance Building. Perhaps the most famous, and most notorious, Chicago inhabitant was Al Capone, the organized crime boss of the Chicago Outfit, who in 1929 ordered the St. Valentine’s Day Massacre on Chicago’s north side.

With its over 2.7 million inhabitants, Chicago is the most populous city in Illinois, as well as the Midwest United States. Bordering Chicago, Lake Michigan provides a dazzling spectacle as far as the eye can see to the east, while several suburbs stretch to the north, west and south. Altogether, roughly 10 million people inhabit the Chicagoland area. The city’s climate is humid continental, with pleasant summers and often bitter winters. Major points of interest include the Museum of Science and IndustryThe Field MuseumThe Art InstituteAdler PlanetariumShedd Aquarium, The Museum of Contemporary Art, Soldier Field, The United Center, Wrigley FieldGuaranteed Rate Field, McCormick Place and Lincoln Park Zoo. Chicago is a major sports city that boasts two professional baseball teams, the Chicago Cubs and Chicago White Sox, a professional hockey team, the Chicago Blackhawks, a pro basketball team, the Chicago Bulls, and a pro football team, the Chicago Bears. Popular 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. Craft beer and wine are popular, as well as Malört, which 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.




The Publishing House Bed and Breakfast

108 North May Street

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), Mad Social (American restaurant), Eyelashes R Us (beauty salon) and more.

This location is 0.1 miles from Harpo Studios, 0.4 miles from Hubbard Street Dance Chicago, 0.6 miles from University of Illinois at Chicago, 0.9 miles from Boeing International Headquarters, Rush University Medical Center and Illinois Medical District, 1 mile from Civic Opera House, 1.1 miles from Willis Tower, 1.3 miles from Chicago Board of Trade Building, 1.5 miles from DePaul University, 1.7 miles from Art Institute of Chicago, Millennium Station and Millennium Park, 4.5 miles from Wrigley Field and 14.3 miles from Chicago O’Hare International Airport.

Approximate cost per night (Sinclair room): $388




The Peninsula Chicago

108 East Superior

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.

You may find Michigan Avenue within feet, Water Tower Chicago and Loyola University Museum of Art 0.1 miles, Water Tower Place, Chicago Museum of Contemporary Art, Ann & Robert H. Lurie Children’s Hospital of Chicago, Northwestern Memorial Hospital and Arts Club of Chicago 0.2 miles, Navy Pier 1.1 miles, Union Station 1.4 miles, Guaranteed Rate Field 4.5 miles and Midway International Airport 9.6 miles from this accommodation.

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

Cost per person (five people): $311




The Langham Chicago

330 North Wabash Avenue

Hotels in Chicago

House Of Blues Chicago

With 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, The Langham Chicago can be found close to 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), House of Blues Chicago (live music venue), Chief Chicago Limo (limousine service), North Loop Market (grocery store), Smith & Wollensky (steak house) and more.

From this hotel Marina City, House Of Blues Chicago, Wrigley Building, Bridgehouse and Chicago River Museum and Chicago Vietnam Veterans Memorial are 0.1 miles, American Medical Association Headquarters, Chicago Tribune Tower, Chicago Theater and Shops at Northbridge are 0.2 miles, Chicago Riverwalk is 0.3 miles, Millennium Station is 0.4 miles, Millennium Park is 0.5 miles, Navy Pier is 1.2 miles, Guaranteed Rate Field is 4 miles, Wrigley Field is 4.4 miles and Midway International Airport is 9.1 miles.

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

Cost per person (four people): $292



Maison De Fashion



Thompson Chicago

21 East Bellevue Place

Where to Stay in Chicago IL

360 Chicago

Thompson Chicago features an on-site restaurant, a fitness center, free daily newspapers, coffee and tea, free WiFi, flat-screen TVs, minibars, bathrobes, deluxe bath amenities and modern rain shower-heads. It’s near Nico Osteria (Italian restaurant), Shinola (watch store), The Frye Company (shoe store), Starbucks, Stil Salon & Spa, Brilliant Earth (jeweler), COS (clothing store), Del Frisco’s (steakhouse), Fabbri Furs, Christian Louboutin, TOM FORD, Fig & Olive (Mediterranean restaurant), Charles Ifergan (hair salon), Jimmy Choo, Tavern on Rush, Luxbar, The Original Pancake House, Carmine’s, Gibsons Steakhouse, Hugo’s Frog Bar and more.

From here Oak Street Beach, 360 Chicago and Loyola University Museum of Art are 0.3 miles, Water Tower Place, Water Tower Chicago, Charnley-Persky House Museum, Ann & Robert H. Lurie Children’s Hospital of Chicago, Chicago Museum of Contemporary Art and Michigan Avenue are 0.4 miles, Oak Street is 0.5 miles, Millennium Station is 1.2 miles, Willis Tower and Chicago Board of Trade Building are 1.6 miles, Guaranteed Rate Field is 4.9 miles and Midway International Airport is 9.8 miles.

Approximate cost per night (penthouse suite): $1,423






Freehand Chicago

19 East Ohio Street

Where to Stay in Chicago IL

Shops at Northbridge

With free WiFi, seating areas, desks, air conditioning, linens, towels, flat-screen TVs, mini-bars, a 24-hour front desk, an onsite bar, a restaurant and a cafe, Freehand Chicago is near Pizzeria Uno, Fleming’s (steakhouse), The Dinner Detective (dinner theater), Weber Grill, The Berkshire Room (lounge), Pops for Champagne (wine bar), Watershed (bar), L.A. Burdick Chocolates, Alliance Patisserie (pastry shop), Adagio Teas, sweetgreen (salad shop), Nespresso USA, Bloomingdale’s, Eataly (Italian restaurant), Joe’s (seafood), Sable Kitchen & Bar and more.

You’ll find American Medical Association Headquarters and Shops at Northbridge 0.1 miles, Blue Chicago, Chicago Tribune Tower and Wrigley Building 0.2 miles, Arts Club of Chicago, Michigan Avenue, Marina City, House Of Blues Chicago and Water Tower Chicago 0.3 miles, Millennium Station 0.6 miles, Millennium Park 0.7 miles, Art Institute of Chicago 0.9 miles, Union Station and Navy Pier 1.2 miles and Chicago O’Hare International Airport 15.4 miles from this locale.

Approximate cost per night (penthouse suite): $1,549

Cost per person (six people): $258


Hotels in New York City



The Chicago Hotel Collection

312 W. Chestnut

Chicago IL Hotels

Oak Street Beach

The Chicago Hotel Collection resembles a field-house and has an on-site bar and restaurant, a 24-hour front desk, a gymnasium lounge, a coffee bar, seating areas, flat-screen TVs, free toiletries and hair dryers. Near here are BIG & little’s Restaurant, Steven Deer Salon, Millennial Mart, Marwen, Kiki’s Bistro (French Restaurant), Savage Smyth (event venue), Revitalab (spa and health club), Mogadishu Restaurant, Bismilahi Restaurant, Flex Pilates Chicago, Haute 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) and more.

This hotel is 0.1 miles from Oak Street, 0.5 miles from Blue Chicago, 0.6 miles from Water Tower Chicago, Loyola University Museum of Art and The Noble Horse Theatre, 0.7 miles from Michigan Avenue, American Medical Association Headquarters, 360 Chicago and Water Tower Place, 0.8 miles from Charnley-Persky House Museum, 1.3 miles from Millennium Park, 1.5 miles from DePaul University and Art Institute of Chicago and 14.8 miles from Chicago O’Hare International Airport.

Approximate cost per night (premium two-bedroom): $341

Cost per person (six people): $56



Certified Piedmontese

The Penthouse at Grand Plaza

540 North State Street

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), Rock Bottom Restaurant, Cantina Laredo (Mexican restaurant), Corey’s NYC Bagel Deli, Grossman & Jack Talent and more.

From this penthouse American Medical Association Headquarters is 0.1 miles, Shops at Northbridge, Chicago Tribune Tower and Wrigley Building are 0.2 miles, Marina City, House Of Blues Chicago, Arts Club of Chicago, Michigan Avenue and Bridgehouse and Chicago River Museum are 0.3 miles, Union Station is 1 mile, Wrigley Field is 4.1 miles and Midway International Airport is 9.3 miles.

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

Cost per person (eight people): $198




The Robey

2018 W North Avenue

Where to Stay in Chicago IL

Wicker Park

The Robey has free WiFi, hardwood floors, 400 thread sheets, flat-screen TVs and an on-site cafe. Cafe Robey, Le Labo Fragrances, Fairgrounds Cafe, Pork & Mindy’s (sandwich shop), reishi (health and beauty shop), The Tankard (pub), TOMS Chicago (shoe store), ENSO Sushi & Bar, Dimo’s Pizza, Shinola (watch store), Timbuk2 (bag store), Potbelly Sandwich Shop, lululemon, The North Face, Northside Bar, benefit (beauty salon), Real Good Stuff Co. (juice shop), Starbucks, Bonci Pizza, Subterranean (bar), Estelle’s (bar), Chop Shop (American restaurant), Tapster (bar) and more are all within range.

You may find Wicker Park 0.2 miles, Congress Theater is 1 mile, DePaul University – Lincoln Park Campus, Steppenwolf Theatre and Steppenwolf Theatre Company are 1.5 miles, United Center and The Noble Horse Theatre are 2.1 miles, Second City, Lincoln Park Zoo and Oak Street are 2.2 miles, Wrigley Field is 2.8 miles, Union Station is 2.9 miles, Navy Pier is 4 miles and Midway International Airport is 9.1 miles from here.

Approximate cost per night (penthouse suite): $699

(high demand – book in advance)






Villa D’ Citta

2230 North Halsted Street

Chicago IL Hotels

Lincoln Park Zoo

Featuring a private grotto and garden with BBQ facilities, free WiFi, flat-screen TVs, Italian-inspired décor, large windows with neighborhood views, a deck with a hot tub, daily continental breakfast, gourmet kitchen access, a hot breakfast on weekends and bicycle rentals, Villa D’ Citta is close to Studios FUSE (physical fitness program), Orangetheory Fitness (gym), Hang 5 Fitness (physical fitness program), Shine (Pan-Asian restaurant), Bluemercury (cosmetics store), Kameya (Japanese restaurant), Athenian Room (Greek restaurant), Liquor Expo (liquor store) and more.

This B&B is 0.4 miles from DePaul University – Lincoln Park Campus, 0.7 miles from Lincoln Park Conservatory, Steppenwolf Theatre Company and Lincoln Park Zoo, 0.8 miles from Steppenwolf Theatre and Peggy Notebaert Nature Museum, 1 mile from Second City, 1.1 miles from Briar Street Theatre, 1.8 miles from Wrigley Field, 3.2 miles from Chicago Board of Trade Building and 13.6 miles from Chicago O’Hare International Airport.

Approximate cost per night (queen room): $547

Cost per person (four people): $137



Hotel Chocolat Stores Ltd



Wrigley Field Penthouse

820 West Newport Avenue

Hotels in Chicago

Wrigley Field

Wrigley Field Penthouse has 2 bedrooms, free WiFi, air conditioning, a garden, a terrace, city views, a balcony, a flat-screen TV and a fully-equipped kitchen. This penthouse is less than a 10 minute walk from Wrigley Field, near which you’ll find Rice’N Bread (Korean restaurant), The Graystone Tavern (bar & grill), Happy Camper (pizza restaurant), Dimo’s Pizza, Roost Chicken & Biscuits (restaurant), Shake Shack, Do-Rite Donuts & Chicken, El Burrito Mexicano (Mexican restaurant), Smoke Daddy BBQ (barbecue restaurant), Jeni’s Splendid Ice Creams (ice cream shop), Bernie’s Tap & Grill, Lucky Dorr (bar), Murphy’s Bleachers (restaurant), Wrigley Rooftops (event venue), Raising Cane’s Chicken Fingers, Big G’s Pizza (pizza restaurant), La Mexicana Grill (Mexican restaurant), Metro (live music venue), The GMan Tavern (bar) and more.

Wrigley Field and Briar Street Theatre are 0.4 miles, Music Box Theatre is 0.8 miles, DePaul University is 1.4 miles, Peggy Notebaert Nature Museum and Lincoln Park Conservatory are 1.6 miles, Aragon Entertainment Center and Aragon Ballroom are 1.7 miles, Lincoln Park Zoo is 2 miles, Steppenwolf Theatre Company is 2.2 miles, Willis Tower is 4.6 miles, Art Institute of Chicago is 4.7 miles and Chicago O’Hare International Airport is 13.2 miles from this penthouse.

Approximate cost per night: $634

Cost per person (six people): $105





So there you have them, 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?


    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? 


  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.


    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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