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As the third largest city in the United States, Chicago is — perhaps unsurprisingly — one of the country's top tourist destinations. It has a bit of everything and for all types of travelers; there are the beaches of Lake Michigan, an incredible architectural history, world-class museums like the Art Institute of Chicago, professional sports played every season and a top-notch dining scene. Of late, a number of gorgeous boutique properties have been debuting across the city, adding to the already stellar field. We’re helping you narrow down your options by picking our favorite Chicago boutique hotels across a variety of categories, from super-chic budget properties to ultra-luxurious accommodations.
Best Overall: Thompson Chicago, a Thompson Hotel
With 247 rooms, the Thompson Chicago pushes the size boundaries of a boutique hotel, but it’s undoubtedly one of Chicago’s swankiest properties. A 2014 renovation saw the interiors revamped with an elegant midcentury-meets-contemporary aesthetic that makes the hotel feel like a luxurious yet relaxed residence. There are quirky elements, too, like funky works of art and industrial-chic filament lights. Located on the Gold Coast, many of the rooms have lake views — made all the better with floor-to-ceiling windows — while others look out onto the famous skyline. Rooms feature a gray palette and modern furniture (including Saarinen Tulip chairs), and bathrooms dazzle with marble counters, white subway tiles and navy blue ceilings. While there’s no spa or pool at the Thompson Chicago, the stars of the show are the restaurant and bar — both of which are popular with locals, so definitely make a reservation in advance. There is, however, a fitness center for those looking to stay in shape.
Best Budget: Longman & Eagle
Longman & Eagle is one of the buzziest restaurants in Chicago, and if you eat so much you can’t make it home, you’re in luck — you can crash in one of six hotel rooms located on the second floor, and usually for less than $100 a night. The Logan Square spot doesn’t really have anything in the way of amenities, save the restaurant, of course, but the rooms are a bit of a hipster heaven. Each is individually decorated, featuring exposed brick or wood walls, artsy prints and photos and even cassette players with house-curated mixtapes. Potential guests should note that the noise from the very, very rowdy bar will permeate the rooms, so it’s a good idea to bring a pair of earplugs. That said, the restaurant and bar are the highlights of the property, and guests often spend a good amount of time there in the evenings. While you're there, try out one of the 150 whiskeys offered by the bar as a nightcap.
Best Historic: Chicago Athletic Association Hotel
Opened in 1893, just in time for the World's Columbian Exposition, the Chicago Athletic Association was originally a men’s sports club for the most elite Chicagoans, housed in a Victorian Gothic tower by Henry Ives Cobb on a prime site on Michigan Avenue. The actual club closed in 2007, and the building was reborn as a 241-room hotel in 2015, with architects and designers working to retain its heritage — like the elaborate woodwork adorning the public spaces, the original Carrara marble and wood flooring and intricate stained-glass windows. Plus, in the rooms, you’ll find vintage athletic equipment woven into the design, like a pommel horse as a bench and tennis racquet grips as nightstand legs. Aesthetics aside, the Chicago Athletic Association Hotel is a foodie’s delight with no less than seven amazing bars and restaurants — most notably, Cindy’s on the rooftop with great views of Millennium Park. For more casual dining, you'll also find a Shake Shack.
Best for Families: Hotel Lincoln, a Joie de Vivre Hotel
Though it’s not in the heart of Chicago’s main tourist area, Hotel Lincoln, a Joie de Vivre Hotel, is in the upscale neighborhood of Lincoln Park, located just a five-minute walk from the Lincoln Park Zoo and a 15-minute walk from the beach — two perfect activities for families. Best of all, the spot even offers free pedicab rides to the two activities. The quirky hotel has a laid-back atmosphere that comes across in its funky decor, like a “wall of bad art” in the lobby. While standard rooms are a little tight, there are family suites with two bathrooms and bunk beds for the kids. Additionally, pets are welcome here (for a fee), so the whole family can stay. On-site dining skews toward the adult side, with the rooftop bar J Parker, the Kennison restaurant and Elaine’s Coffee Call. Even though kids are welcome at the restaurant for dinner, if they’re tired, room service is available.
Best for Romance: St. Jane
The brand-new St. Jane hotel, which just opened in July 2018, is the place to go for a romantic getaway in Chicago. Named after the Nobel Peace Prize winner (and native Chicagoan) Jane Addams, a social reformer, the 365-room property sits in an Art Deco building that was formerly the home of the Hard Rock Hotel, but today, the atmosphere is more in the realm of relaxed luxury than rock and roll. Standard rooms are lovely, with white walls, elegant moulding on the ceiling, and pink accents, but for the most romantic experience, you’ll want to upgrade to The Tower, a hotel-within-the-hotel that is even more luxurious than the main property. There are only 33 suites here — all on floors 25 and up — and they’re decorated with dark gray walls, domed headboards and modern art. Guests of The Tower have complimentary access to 24th-floor lounge The Nobel, a romantic rooftop spot that is only open to other hotel guests for a fee.
Best for Luxury: Soho House Chicago
This hotel-meets-private-club is the definition of industrial chic, sitting in a century-old warehouse in the West Loop. While the amenities of Soho House are typically for members only, the hotel can be booked by the public and access to all amenities is included when you stay as a guest. Forty rooms are divided into three categories — Tiny and Small, Medium and Medium Plus, and Big — which range in size from 200 square feet to 600 square feet and have gentlemanly decor like dark wood furniture, patterned rugs and brass detailing. (Splurge on a Big room to get an incredible freestanding tub.) You’ll, of course, want to spend time enjoying Soho House’s amenities, like the 17,000-square-foot gym that has a boxing ring and offers group classes, the indulgent Cowshed Spa and the gorgeous rooftop pool. Then there are the restaurants and bars. Three are open to the public, but head to the House Kitchen grill or Roof for an air of exclusivity.
Best Hostel: Freehand Chicago
Housed in the former Tokyo Hotel building in the ever-popular River North neighborhood, the Freehand Chicago is a glamorous hostel-hotel hybrid with 80 shared rooms (for four people each) and 135 singles — each with a private en-suite bath. (There are also two penthouse suites for those who want to splurge.) The entire property exudes a retro-cool vibe, with wood trim and paneling, vintage-looking tilework and plenty of colorful textiles. Amenities are a bit limited — there’s a small fitness center, a shared kitchen for home-cooked meals and a café for dining out — but the real attraction here is the popular Broken Shaker bar, a staple of the Freehand brand. This cocktail den attracts locals and guests alike with its stellar cocktail menu. Don’t miss happy hour from 4 p.m. to 6 p.m. Monday to Friday!
Best Design: The Robey
Located in trendy Wicker Park, the Robey Hotel is housed in a wedge-shaped building originally built in 1929 as an office but reopened as a 69-room hotel in 2016. Though the design-forward property nods to the property's heritage with the building's original directory in the lobby and Art Deco design elements in the public spaces, the majority of rooms are more subdued spaces with midcentury-inspired furniture in neutral hues with jewel tone accents. There are also Annex Lofts that take on an industrial vibe with white brick and concrete — these rooms have extra beds for larger groups or families. There’s a café and a lounge that are great for meals or drinks, but the real stunners are the rooftop bar with a terrace and the sixth-floor Cabana Club, which is also outdoors, has a pool and offers great views of the skyline. The latter is the perfect summertime hotspot, so be prepared for some crowds.
Best Apartment-Style: The Guesthouse
For travelers looking for a homier stay, The Guesthouse provides a residential vibe — and plenty of space for each guest via 25 one-, two- and three-bedroom apartments with full kitchens and in-unit laundry. The tradeoff, however, is that it’s located about eight miles from the city center, in the neighborhood of Andersonville. But with such spacious and well-appointed accommodations, we think it’s worth the trek. (For what it’s worth, public transportation can easily get you to the city center.) It’s important to remember that this is a true hotel, too, despite the large room sizes: there’s a 24-hour front desk, a gym, a business center, a gift shop and a communal roof deck. Though there’s no on-site restaurant, the hotel has partnered with local eateries that will deliver directly to your room. Similarly, you can get a spa treatment in your room, or you can visit a full-service spa just next door.