Sprawling chain hotels can be a total snooze (although Chicago boasts some beauties in its best hotels). Luckily, the Windy City has an impressive assortment of boutique properties that trade size for warm, personalized service and lashings of character. Whether it's your first time here or you're planning a cheeky staycation, these hotels make a cozy backdrop when you're away from home. Take a look at our all-time favorites—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.
RECOMMENDED: Find more places to stay with our guide to the best downtown Chicago hotels in the Loop
Best boutique hotels
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—throwbacks to the club rooms of athletic associations long gone. But 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.
Straight from the streets of central London, is this fab British import, which functions as a private members' club meets unique boutique hotel. Each of the 40 rooms come with king-sized beds, Egyptian cotton sheets andwalk-in rainforest showers. If you book one of the Big Rooms, you also get 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.
In a landscape filled with mega-hotels and Airbnb rentals galore, there’s something extra special about a good old bed and breakfast. The quaint but impressive Publishing House has 11 unique rooms (from cozy to XL) that are outfitted in cowhide rugs, clawfoot tubs and funky vintage furniture. Each room is wildly different, giving guests an excuse to venture back again and again. As much as you won’t want to leave your room in the morning, one whiff of breakfast—cooked by owners Shawn Uldridge and Kimberly Lowery—will surely draw you out of bed.
Staying at the Freehand is like crashing at your ubercool friend's very stylish pad. The rooms at this hybrid hotel-hostel are small but 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.
When family comes to town (or you just want a low-key staycation), the Guesthouse Hotel is a charming base for exploring Andersonville or the north side. Each room is a two- or three-bedroom suite with a kitchen (stocked with cookware and glasses), a balcony with a grill and a washer-dryer. While the hotel is located within a few blocks of excellent restaurants and bars (and each room comes with a helpful guide to the neighborhood offerings), you can also have ingredients delivered to cook yourself in the kitchen or order meals from local spots, including Calo Ristorante and Southport Grocery. The hotel also has free wifi, as well as a small gift shop with locally made products.
Clean mid-century design and effortless luxury in the heart of Chicago, the Thompson Hotel 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. The hotel features an on-site fitness center, too.
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.
Gadget geeks will get a kick out of techie amenities, like flat-screen TVs concealed behind bathroom mirrors and mechanized drapery, at this 63-room property in Loop- and River North-adjacent Streeterville. It’s all of a piece with the faintly futuristic vibe that dominates here, from cool white textiles and angular armchairs in guest rooms to 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.
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 and renamed The Alise, although it's now dubbed 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.
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.
This comfortable Gold Coast hotel recently received a four-month interior makeover spearheaded by 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, sophisticaed design touches.