Literature, sports, comedy, history, architecture; there are a number of reasons to visit the metropolis on Lake Michigan. But Chicago’s best hotels are so good they become destinations in their own right.
Lovers of mid-century styles and Art Deco architecture will be in heaven in this city and the hotel scene offers a number of different playful interpretations of the historic styles that characterize the aesthetic of this city.
We’ve rounded up a selection that stands out, like a design hotel built in a former gymnasium or a chic hideaway inspired by a pioneering modernist sculptress. And there’s a warm All-American to match. Take vacation notes – and interior design.
The best hotels in Chicago
1. The publishing house
In 1909, this West Loop building began life as a Free Methodist publishing house. Today, it’s a sophisticated 11-room boutique hotel, where each of the individually designed rooms recalls the building’s history, with rooms dedicated to different Chicago literary personalities, such as Saul Bellow and Stuart Dybek.
The look is confident and comfortable mid-century modern, with lots of exposed brick and painted woodwork, accented with modernist furniture and fixtures.
The decor’s vibe is more boutique hotel than bed and breakfast, but there’s a homey welcome from the wife and husband team who run it, with snacks and sodas on offer and a hearty breakfast.
The downside: the (almost) dozen rooms in this hotel are so popular that it is often full, so book early!
Book a stay at The Publishing House Bed and Breakfast (opens in a new tab). Rooms start around $200.
2. Chicago Athletic Association
Housed in an 1893 building, originally a sports club with members of various famous local athletes (hence the name), this hip hotel has quickly become a downtown Chicago mainstay.
The original purpose can be seen throughout, with a design loosely based on an early 20th century sports club. There’s a distinct vintage Americana feel, with generous portions of wood and leather.
Design highlights include the Cherry Circle Room restaurant’s sleek curved bar and repurposed vintage gym equipment.
Book a stay at the Chicago Athletic Association (opens in a new tab). Rooms from $190.
3. The Robey
The Robey is located inside a distinctive art deco building formerly known as the Northwest Tower. You will immediately notice the main building with its distinctive triangular shape, somewhat reminiscent of Manhattan’s Flat Iron.
It’s located in the trendy and buzzing Wicker Park neighborhood and its own rooftop bars are part of the area’s buzzing food and drink scene.
The former office building has been reborn into an 89-room hotel under the direction of Belgian design duo Nicolas Schuybroek Architects and Marc Merckx Interiors.
In the main office building you will find the “Tower Rooms” and rooftop spaces, then there are 20 “Annex Loft” suites in an adjoining structure, a 1905 building that was once the fireproof Hollander warehouse. The industrial space has been transformed by the DELORDINAIRE architects, while retaining some period touches.
Book a stay at La Robey (opens in a new tab). Rooms from $350
4. Chicago Freehand
Once again housed in a building from the 1920s, this boutique hotel from the Freehand group was designed by the famous New York firm Roman and Williams. They kept the sign outside the previous business, “Tokyo Hotel”.
It’s stylish but very reasonably priced, with comfortable bunk bed options for families.
The decor is inspired by a vintage Midwestern aesthetic: think dark wood light fixtures, sleek vintage wallpaper, and colorful modernist patterns.
The craft cocktail bar, Broken Shaker, is a local favorite.
Stay at Freehand Chicago (opens in a new tab). Rooms start around $175.
5. Soho House Chicago
Soho House always hits the mark in terms of style, and their rooms attached to the Chicago branch are no exception.
The house is located in a former belt factory and period details include reclaimed hardwood floors, period tile and a hall wall clad in the wood of the original rooftop water tower of the building.
Today, the rooftop is home to the band’s signature rooftop pool, adjoining Chicago’s rooftop Italian restaurant.
The rooms have these cute vintage looking Marshall Bluetooth speakers and Cowshed products.
The hotel can only be booked by Members and Friends.
Book a stay at Chicago Soho House (opens in a new tab). Rooms from $240.
6. The Hoxton, Chicago
The essential London hotel group opened its third address in the United States in 2021 in the former meat district of Fulton Market/West Loop.
It has all the hallmarks we’ve come to expect from the London-based group: a laid-back, creative atmosphere with a polished finish, decor that hints at the locality, and great food and drink options.
In the rooms, you’ll find floor-to-ceiling industrial windows and, you guessed it, exquisite mid-century modern furnishings. We particularly like the modernist motifs on the bedspreads and the elegant armchairs that could come straight out of the Mad Men decor.
In the rooftop bar, Cabra, stunning design details like rich green tiles and decorative lanterns are set against the backdrop of Chicago’s skyscrapers through huge windows. The rooftop pool, dotted with pastel-pink tiles and furniture, also offers fabulous skyline views.
Book a stay at The Hoxton, Chicago (opens in a new tab). Rooms start around $350.
7. The Gwen Hotel
The hotel is named after and inspired by Chicago-born abstract sculptor Gwen Lux (her work is well worth a look, by the way). Lux artwork features on the elegant facade and there’s an overall Art Deco aesthetic with lots of curved lines and gold embellishments.
The luxury hotel is located on the very chic “Magnificent Mile” and enjoys an excellent reputation, for its rooms and its rooftop bar and restaurant Upstairs at the Gwen.
All rooms have large windows overlooking the Chicago skyline and are adorned with chic, comfortable modernist furnishings and artwork that pays homage to the style of Gwen Lux.
The hotel offers an “urban glamping experience” (pictured below), inviting guests to camp among the city’s skyscrapers.
The on-site Italian restaurant Nico Osteria is a favorite of local and visiting foodies.
Book a stay at Hotel Gwen (opens in a new tab). Rooms from $500
The ambitious yet comfortable Hotel Thompson is located in one of Chicago’s most upscale neighborhoods in the Gold Coast neighborhood.
The design respects the classic Art Deco feel of the building, with modernist art features and lots of curved lines in the furniture, but it’s far from musty. There are Joe Perez wall prints and the much-loved subway tiles in the bathrooms.
Brit Tara Bernerd is the designer behind the look and at the time of the hotel’s opening she described the feel as “raw luxury”.
Book a stay at Thompson Chicago (opens in a new tab). Rooms from $300.