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Photograph: Courtesy Freehand Chicago

The 10 best boutique hotels in Chicago

Treat yourself to a stay in one of the most special and unique hotels in Chicago

Written by
Cate Huguelet
&
Morgan Olsen
Contributors
Rhys Thomas
,
Lola Christina Alao
&
Alex Floyd-Douglass
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While massive hotel chains aren't for everyone, Chicago boasts some of the best hotels, which you should totally check out. Thankfully, the Windy City has an impressive assortment of boutique properties that trade size for warm, personalized service and a huge helping of character. And these are things we certainly look for in our hotels here at Time Out.

Whether it's your first time here or you're planning a cheeky staycation, these boutique hotels make a cozy backdrop when you're away from home. Our top picks range from a stylish stunner in Wicker Park to a British import crowned by one of the city’s best rooftop pools. With choices like these, you'll be packing your bags in no time. Happy vacations, people. Or maybe even a staycation? Because any excuse to stay in some of these...

Find more places to stay with our guide to the best downtown Chicago hotels in the Loop. Or stay one of the coziest Airbnbs near Chicago this winter. Feeling fancy? Check out the most lavish Airbnbs in Chicago. Feeling quirky? Here's the most unique Chicago Airbnbs.

Who makes the cut? While we might not stay in every hotel featured, we've based our list on top reviews, hosts and amenities to find you the best stays. This article includes affiliate links. These links have no influence on our editorial content. For more information, see our affiliate guidelines. 

Best Chicago boutique hotels

  • Hotels
  • Boutique hotels
  • Gold Coast

Clean, chic, and effortlessly cool, the Thompson Chicago is a boutique centerpiece on the Gold Coast. The hotel's amazing restaurant, Nico Osteria, offers authentic and light Italian seafood while the in-house bar and gathering space Salone Nico serves crafted cocktails and a fine Italian and Meditteranean wine list. If you need to work off that hangover, luckily for you, the hotel features an on-site fitness center, too.

Mood? Contemporary chic. 
Location perks? Nestled in the city center.
Budget range? Well priced.

  • Hotels
  • B&Bs
  • West Loop

In a landscape filled with mega-hotels and Airbnb rentals galore, there’s something extra special about a good old bed and breakfast. Especially one as good as this. The quaint but impressive Publishing House has 11 unique rooms (from cozy to XL) that are kitted out in cowhide rugs, clawfoot tubs, and funky vintage furniture. Each room is wildly different, giving guests an excuse to return for more again and again. As much as you won’t want to leave your room in the morning, one whiff of breakfast will surely draw you out of bed (it’s very good here).

Mood? Sustainable luxury. 
Location perks? In West Loop, within easy walking distance of most attractions.
Budget range? Mid-range.

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  • Hotels
  • Boutique hotels
  • Loop

To say the Chicago Athletic Association is beautiful is, to put it mildly. The gorgeously restored and revamped hotel, opened in 2015, boasts over 200 luxury boutique rooms. It also sports plenty of features to make it a favorite of Chicago residents, from the unparalleled view of Millennium Park and Lake Michigan at Cindy’s rooftop restaurant to more great food and drink at Cherry Circle Room (with its private alley entrance) and even a Shake Shack. You’ll also love the Game Room, with bocce, shuffleboard, and billiards to supplement its terrific cocktails; for a special occasion, book in advance for the eight-seat Milk Room bar stocked with ultra-rare spirits.

Mood? Landmark living. 
Location perks? Rooftop views overlooking Lake Michigan. 
Budget range? Surprisingly affordable. 

  • Hotels
  • Boutique hotels
  • River North
  • price 2 of 4

Staying at the Freehand is like crashing at your uber-cool friend's very stylish pad. The rooms at this hybrid hotel-hostel are cozy and highly designed with funky textiles and bunk beds in the shared rooms. Downstairs, guests can enjoy excellent craft cocktails and indulgent bites at the lobby bar Broken Shaker. Because the hotel is located in the heart of River North, you'll be a stone's throw from major tourist attractions and some of the best restaurants and bars the city has to offer.

Mood? Utopian delight.
Location perks? Located on Chicago's River North. 
Budget range? An absolute steal.

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  • Hotels
  • Boutique hotels
  • Uptown
  • price 3 of 4

Whenever loved ones are visiting (or you just need a quick staycation), the Guesthouse Hotel is a really charming base for some exploration of Andersonville or the north side. Each room is a two- or three-bedroom suite with a kitchen (stocked with cookware and glasses, naturally), a balcony with a grill, and a washer-dryer. While the hotel is located within a few blocks of some of the city’s finest restaurants and bars, you can also have ingredients delivered to cook yourself in the kitchen or order-in meals from local spots. Sounds good to us.

Mood? Eclectic vibes.
Location perks? Located between Lincoln Square and Uptown. 
Budget range? Mid to high-end.

Hotel Lincoln
  • Hotels
  • Boutique hotels
  • Lincoln Park
  • price 2 of 4

The complete overhaul of this 12-story Lincoln Park hotel (formerly a Days Inn) is Joie de Vivre’s first in Chicago. It offers 184 guest rooms, clever artwork (quirky paintings on a lobby wall were sourced from Lincoln Park yard sales), room service from The Kennison, and a coffee shop, Elaine's Coffee Call, featuring La Colombe java. The hotel’s rooftop bar, The J. Parker, is a lively hot spot, offering views of the park and skyline.

Mood? Cozy convenience. 
Location perks? Lincoln Park views all round.
Budget range? Cheap and cheerful.

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  • Hotels
  • Boutique hotels
  • Loop
  • price 2 of 4

This Loop hotel in the Reliance Building, built in 1895 and now on the National Register of Historic Places, was known as the Hotel Burnham from 1999 to 2016 when it was bought by a small West Coast boutique chain called Pineapple Hospitality. Today, it's known as Staypineapple, matching another property the company owns in San Francisco. Designed by famed architect Daniel Burnham, along with Charles Atwood and John Root, the building still features the original ornate grillwork on the elevators. The ground-floor restaurant, formerly the Atwood Café, is now simply called Atwood following a spiffy remodel. Perfect for visiting architecture buffs.

Mood? Bespoke design. 
Location perks? Certain suites offer Lake Michigan views.
Budget range? A great deal.

  • Hotels
  • Boutique hotels
  • River North

This extremely modern Chicago hotspot is filled with tons of tech amenities, like the 42" flat-screen TVs. Some rooms even feature a separate living room. It's located near North Side, putting you in the heart of Chicago should you decide to stay here. This boutique hotel is also just steps from the Magnificent Mile. If you feel like dining and drinking here, you can take a seat on their sky terrace rooftop lounge and have a small bite to eat or make the most of their happy hour.

Mood? Boutique chic. 
Location perks? Two blocks from Magnificent Mile. Magnificent indeed.
Budget range? Great offering. 

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  • Hotels
  • Boutique hotels
  • Rush & Division

The newly redesigned Talbott hotel – transformed from an old-school hideaway to a bright, modern city escape – is the perfect place for a staycation. It's in the center of the Gold Coast, just a stone's throw away from the nightlife, shopping, and dining. In your room, you'll find a flat-screen TV with HD channels and free WiFi. Some suites are even equipped with a living area and sofa for ultimate relaxation. Plus, the hotel has its very own restaurant, where you can find American bistro classics for breakfast, lunch, and dinner.

Mood? Super glamourous.
Location perks? Situated downtown, within walking distance from Magnificent Mile. 
Budget range? Extremely good value. 

Sophy Hyde Park
Photograph: Courtesy Booking.com

10. Sophy Hyde Park

This crafty boutique hotel celebrates art and artists. Every corner of the place is covered in unique murals and paintings, from the floor-to-ceiling colourful abstract paintings behind the beds or the arts and crafts style doodle-strewn ceiling in the bar. Hit up the swanky bar and restaurant for locally sourced plates, or head to the alfresco terrace festooned with string lights for post-dinner drinks. 

Mood? Eclectic luxury.
Location perks? Tucked away in the Hyde Park neighbourhood, less than a mile away from The University of Chicago and the Museum of Science and Industry. 
Budget range? Good value. 

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