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Photograph: Courtesy Freehand Chicago

The best boutique hotels in Chicago

Treat yourself to some of the most special and unique hotels in Chicago

Written by
Cate Huguelet
&
Morgan Olsen
Contributor
Rhys Thomas
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Massive hotel chains aren't for everyone (though, that being said, Chicago does boast 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 those are things are like 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...

RECOMMENDED: Find more places to stay with our guide to the best downtown Chicago hotels in the Loop

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Best boutique hotels

  • 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).

  • 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 241 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.

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

Staying at the Freehand is like crashing at your ubercool friend's very stylish pad. The rooms at this hybrid hotel-hostel are cosy and highly designed with funky textiles and bunk beds in the shared rooms. Downstairs, guests can grab coffee and pastries at Cafe Integral or belly up for excellent craft cocktails at 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. 

  • 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.

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Thompson Chicago
  • Hotels
  • Boutique hotels
  • Gold Coast

Cleann, chic and effortlessly cool, the Thompson Chicago is a boutique centerpiece in the Gold Coast. The hotel's amazing restaurant, Nico Osteria, offers authentic and light Italian seafood while 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, he hotel features an on-site fitness center, too.

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.

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  • Hotels
  • Boutique hotels
  • River North

Gadget geeks will get a kick out of the techie amenities at this Chicago hotspot: think flat-screen TVs concealed behind bathroom mirrors and mechanized drapery. This 63-room property is filled with cool white textiles and angular armchairs in guest rooms, hallways lined with abstract artwork and pillars of glowing light. For a dose of relaxation, splash out on one of the hotel’s suites, which feature spacious marble-clad bathrooms fitted with rainfall showers and soaking tubs.

  • 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.

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The Robey

Situated at the heart of hipster haven Wicker Park, this 69-room hotel—the long-awaited reimagining of the 1929 Art Deco Northwest Tower—earns coolness cred for its common spaces, like the French-accented Café Robey and rooftop pool-adjacent Cabana Club, appointed in a sleek palette of whites and grays. But for the minimal vibe of its public face, its mix of queen, king, and suite-style rooms aren’t without homey creature comforts; think crisp 400-thread-count linens, supple denim robes, Bluetooth sound systems and, thanks to the building’s unusual triangular shape, an abundance of windows that usher in natural light.

  • Hotels
  • Boutique hotels
  • Rush & Division

Not too long ago, this comfortable Gold Coast hotel received a four-month interior makeover thanks to Chicago designer Kara Mann, who transformed the space from an old-school hideaway to a bright, modern city escape. Situated in the heart of the Gold Coast, it’s an ideal launching pad for a staycation—guests are just around the corner from Michigan Avenue shopping, Oak Street Beach and the MCA. Back in your room, you'll find plush bedding, handsome furniture and clean, sophisticated design touches.

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  • Hotels
  • West Loop

Straight from the streets of central London, Soho House functions as a private members' club but also, you know, a unique boutique hotel. Each of the 40 rooms come with king-sized beds, Egyptian cotton sheets and walk-in rainforest showers. Book one of the Big Rooms for a free-standing tub, dining table and sitting area. While all members can use the plush screening room, Cowshed spa, gym (with a pro boxing ring!) and 60-foot rooftop pool, hotel guests get exclusive access to an array of other spaces, such as the intimate vintage drawing room.

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