Where to Stay in Chicago IL

If you’re looking for information on where to stay in Chicago IL then we have some great recommendations for you! Penthouses are a way to travel luxuriously yet affordably, especially when traveling in a group. Where to stay in Chicago IL does not have to be a challenging and time-consuming question. Here we’ve put together a straightforward list to help you find your perfect Chicago accommodation, penthouse-style! Also included are the best nearby local attractions. Your quest regarding where to stay in Chicago IL starts now!

Chicago, with its over 2.7 million inhabitants, is the most populous city in both Illinois and the Midwest United States. Bordering Chicagoland is Lake Michigan to the east and several suburbs to the north, west and south. Altogether the Chicagoland area is home to roughly 10 million people.

Chicago is largely known for its sports, food and finance. Chi-town is one of the few United States cities with two professional baseball teams, the Chicago Cubs on the Northside and the Chicago White Sox on the Southside. The Chicago Bears (football), the Chicago Blackhawks (hockey) and the Chicago Bulls (basketball) make up the other professional teams. Great food can be found throughout Chicagoland. The finance and big business sector is located in the south Loop area, where the Chicago Board of Tradeand Willis Tower are located.

This most populous Midwest city is home also to some very fine museums such as the Museum of Science and IndustryThe Field MuseumThe Art InstituteAdler PlanetariumShedd Aquarium and The Museum of Contemporary ArtLincoln Park Zoo is a fun and free experience, especially for the kids.

Where to stay in Chicago IL is a great question and we think you’ll find your perfect accommodation from the list below.

 

Reserve Collection Penthouse in the Loop

25 West Randolph Street

Where to Stay in Chicago IL

What’s nearby?

Reserve Collection Penthouse offers 3 bedrooms, a living room, a fully equipped kitchen, free WiFi and air conditioning. Near this Loop penthouse you’ll find: The Dearborn (urban American tavern), Magnolia Bakery, Disney Store, Latinicity (food hall + lounge), AMC DINE-IN Block 37 (movie theater), Block 37 (shopping mall), Godiva Chicago, CHANEL, Macy’s, Old Navy, Argo Tea, Garrett Popcorn Shops, Paul Young Fine Jewelers, James M. Nederlander Theatre, Gene Siskel Film Center, Roti Modern Mediterranean, Atwood (seasonal American fare), Nordstrom Rack, H&M and more.

Millennium Park is 0.3 miles, Chicago Theatre is 0.1 miles, Union Station is 0.7 miles and O’Hare Internaional Airport is 15.6 miles from this location.

Approximate cost per night: $1,240

Cost per person (ten people): $124


 

 

 

Thompson Chicago

21 East Bellevue Place

Where to Stay in Chicago IL

What’s close?

Thompson Chicago offers a penthouse suite and amenities such as 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.

This property is 0.3 miles from Oak Street Beach, 0.4 miles from Water Tower Place, Chicago Museum of Contemporary Art and Michigan Avenue, 1.4 miles from Navy Pier and 15.2 miles from O’Hare International Airport.

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

 

 

 

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Freehand Chicago

19 East Ohio Street

Where to Stay in Chicago IL

River North

With a penthouse suite option, free WiFi, seating areas, desks, air conditioning, linens, towels, flat-screen TVs, mini-bars a 24-hour front desk, a onsite bar/restaurant and 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.

This location is 0.2 miles from Chicago Tribune Tower and Wrigley Building, 0.3 miles from Michigan Avenue and House of Blues, 0.7 miles from Millenium Park, 1 mile from Willis Tower and 15.4 miles from O’Hare International Airport.

Approximate cost per night: $1,549

Cost per person (six people): $258


 

 



FieldHouse Jones

312 W. Chestnut

Where to Stay in Chicago IL

Oak Street Beach

FieldHouse Jones 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. This hotel is near: 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.

Oak Street Beach is 700 feet, Michigan Avenue is 0.7 miles, Navy Pier is 1.7 miles, Wrigley Field is 3.6 miles and O’Hare International Airport is 14.8 miles from this location.

 

Approximate cost per night: $341

Cost per person (six people): $56

 

 

Penthouse Rentals in Miami

 

The Penthouse at Grand Plaza

540 North State Street

Where to Stay in Chicago IL

Michigan Avenue

The Penthouse at Grand Plaza offers a rooftop swimming pool, a sun deck, a fitness center, a basketball court, 3 bedrooms, 3 bathrooms, 3 balconies, 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.

Marina City, House of Blues and Michigan Avenue are 0.3, Art Institute of Chicago is 0.9 miles, Willis Tower is 1 mile and O’Hare International Airport is 15.4 miles from this location.

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

Cost per person (eight people): $198

 

 

Kendo - Kat Von D Beauty

 

Architectural Loop Penthouse

182 West Lake Street

Where to Stay in Chicago IL

Lyric Opera of Chicago

Offering 3 bedrooms, a living room, a fully-equipped kitchen with dishwasher and microwave, a flat-screen TV, a washing machine, city views and free WiFi, this loop penthouse is close to: Ajida Ramen, Jo Chicago (hair salon), Surmesur (custom menswear), Prime & Provisions (fine dining restaurant), Costa Vida (Mexican restaurant), Boar’s Head Cafe, Veggie Grill, Goodwin’s (American restaurant), Mixed Greens (salad shop), Diana’s Nail & Spa, Whimsical Candy, 5411 Empanadas, Big Shoulders Coffee, Rosati’s (pizza restaurant), Asada Chicago (Mexican restaurant), La Cocina (Mexican restaurant), Crepe Bistro (French restaurant), Off the Tracks Grill, The UPS Store, Monk’s Pub, Pierogi Heaven, Philip Di Ciminna Barber Shop and more.

Chicago River Walk and Cadillac Palace Theatre are 0.1 miles, Lyric Opera of Chicago is 0.3 miles, Willis Tower is 0.5 miles, Navy Pier is 1.6 miles and Midway International Airport is 8.8 miles from this location.

Approximate cost per night (three-bedroom penthouse): $670

Cost per person (eight people): $83

(high demand – book in advance)


 

 

 

 

The Robey

2018 W North Avenue

Where to Stay in Chicago IL

Wicker Park

This Wicker Park hotel has a penthouse suite, free WiFi, hardwood floors, 400 thread sheets, flat-screen TVs, an on-site cafe and is near: 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), Angry Pig Tavern and more.

The Robey is 1 mile from Congress Theater, 2.1 miles from United Center, 2.2 miles from Second City and Lincoln Park Zoo, 2.8 miles from Wrigley Field and 12.5 miles from O’Hare International Airport.

Approximate cost per night (penthouse suite): $699

(high demand – book in advance)

 

 

Cashmere in Love

 

 

Wicker Park Penthouse

1719 W Pierce Ave

Where to Stay in Chicago IL

What’s in the vicinity?

Measuring 2,500 square feet this two-bedroom Wicker Park Penthouse can be found near: I Love Kickboxing, Modern Gentlemen Salon, Celebrity Skin, Infiniteus (juice bar), The Delta (cocktail bar), Orange Theory Fitness, Salon Blonde, North Bar, Avenue N Guitars, Gallery Cafe, Uni Sushi, Diplomatic Seventeen Fifty (consignment shop), Pure Barre (fitness class), Las Palmas (Mexican restaurant), Lucia (Italian restaurant) and more.

From here you’ll find Steppenwolf Theatre 1.2 miles, DePaul University – Lincoln Park Campus and Congress Theater 1.3 miles, The Noble Horse Theatre 1.7 miles, Second City, Oak Street and Lincoln Park Zoo 1.9 miles, Wrigley Field 2.8 miles, Millennium Park 3.1 miles and Chicago O’Hare International Airport 12.9 miles.

Approximate cost per night: $515

Cost per person (four people): $128


 

 

 

 

Corner Balcony Penthouse

750 North Wabash Avenue

Where to Stay in Chicago IL

What’s going on?

Steps from Michigan Avenue, this corner balcony penthouse is close to: Holy Name Cathedral Parish, Chick-fil-A, Loyola University of Chicago, Alfredo’s Barber Shop, Friends Ramen, Friends Sushi on State, Golden Needle Tailoring, Devon Seafood Grill, Sunny Side Up & Coffee Shop, Sport Clips Haircuts, Giordano’s (pizza), Potbelly Sandwich Shop, Downtown Dogs, Pippin’s Tavern, Streeter’s Tavern, Stiles Chiropractic Offices, Flaco’s Tacos, Wow Bao (Chinese restaurant), Forever Yogurt and more.

Water Tower Place is 0.2 miles, Millennium Park is 1 mile, Willis Tower is 1.3 miles and O’Hare International Airport is 15.3 miles from this location.

Approximate cost per night: $743

Cost per person (five people): $148

 

 

 

Bloomingdale's

 

 

 

Printers Penthouse

W Polk St. and S Clark St.

Where to Stay in Chicago IL

Near here?

Printers Penthouse has 3 bedrooms, a fully-equipped kitchen with dishwasher and microwave, a flat-screen TV, free WiFi, a shared lounge, 24-hour front desk, spa and wellness facilities with a hot tub and sauna and an on-site casino. You will find close to this location: Umai, LO Spa and Nails, Pat’s Pizza, Sociale (small plates restaurant), Dollop Coffee, Half Sour (cocktail bar), First Draft (craft beer house), South Loop Strength & Conditioning, Sofi Restaurant (Italian restaurant), Sandmeyer’s Bookstore and more.

This location is 0.4 miles from the Chicago Board of Trade, 0.5 miles from Willis Tower, 0.6 miles from Art Institute of Chicago and Union Station, 0.9 miles from Shedd Aquarium and 15.8 miles from O’Hare International Airport.

Approximate cost per night: $893

Cost per person (six people): $148

 

 

 

So there you have it, a concise list of Chicago’s top penthouse rental options. We hope that you have found this information as wonderful as we have and most of all, that you enjoy your Chicago trip!

49 Replies to “Where to Stay in Chicago IL”

  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

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