Literature, sports, comedy, history, architecture; there are any number of reasons to visit the metropolis on Lake Michigan. But the best hotels in Chicago are so good that they're becoming destinations in their own right.
Lovers of mid-century stylings 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 this city's aesthetic.
We've rounded up a selection that stand out, like a design hotel built in a former gymnasium or a chic bolthole inspired by a trailblazing modernist sculptress. And there's a cozy All-American welcome to match. Take vacation - and interior design - notes.
The best hotels in Chicago
1. The Publishing House
Back in 1909, this building in West Loop started life as the Free Methodist Publishing House. Today it's a sophisticated 11-room boutique hotel, where each of the individually designed room nods back to the building's history, with rooms dedicated to different Chicago literary figures, such as Saul Bellow and Stuart Dybek.
The look is confident and comfortable mid century modern, with plenty of exposed brick and painted wooden paneling, embellished with modernist furnishings and light fixtures.
The feel of the décor is more boutique hotel than bed and breakfast, but there's an intimate welcome from the wife and husband team who run it, with snacks and sodas on offer and a generous breakfast.
The downside: this hotel's (almost) dozen rooms are so loved that it's often fully booked, so reserve early!
Book a stay at The Publishing House Bed and Breakfast. Rooms from around $200.
2. Chicago Athletic Association
Old-school Americana glamor at the Cherry Circle bar
Housed in an 1893 building ,originally a sports club where various famous local athletes were members (hence the name), this funky hotel has quickly become a mainstay of downtown Chicago.
The original purpose is seen throughout, with design loosely based on an early 20th century sports club. There's a distinct vintage Americana feel, with generous helpings of wood and leather.
The décor strongly alludes to the building's past
Design highlights include the elegant curved bar at the Cherry Circle Room restaurant and the repurposed vintage gymnastics equipment.
Book a stay at Chicago Athletic Association. Rooms from $190.
3. The Robey
The Robey is set inside a distinctive art deco building formerly known as Northwest Tower. You'll notice the main building at once with its distinctive triangular shape, somewhat reminiscent of the Flat Iron in Manhattan.
It's located in the hip and buzzing Wicker Park area and its own rooftop bars form part of the area's vibrant food and beverage scene.
The former office building was reborn as an 89-room hotel under the direction of Belgian design duo Nicolas Schuybroek Architects and Marc Merckx Interiors.
In the main office building you'll find the "Tower Rooms" and the rooftop spaces and then there are 20 "Annex Loft" suites in an adjoining structure, a 1905 building that was once the Hollander Fireproof Warehouse. The industrial space has been transformed by DELORDINAIRE architects, while keeping some period touches.
Book a stay at The Robey. Rooms from $350
4. Freehand Chicago
Housed once more in a 1920s building, this boutique hotel from the Freehand group, was designed by the famous NYC firm Roman and Williams. They've kept the sign outside from the previous business, 'Tokyo Hotel'.
It's stylish but very reasonably priced, with cozy bunk bed options for families.
Freehand Chicago are evocative of retro train cabins
Decor is inspired by a vintage Midwestern aesthetic: think dark wood fixtures, natty vintage wallpaper and colorful modernist motifs.
The artisanal cocktail bar, Broken Shaker, is a local favorite.
Stay at Freehand Chicago. Rooms from around $175.
5. Soho House Chicago
One of the stylish bedrooms at Soho House Chicago
Soho House always hits the mark style-wise, 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, vintage tile and a lobby wall clad in the wood from the building’s original rooftop water tower.
These days, the roof is home to the Group's signature rooftop pool, neighboring the rooftop Chicago Italian restaurant.
The look is old-school but slinky
Rooms feature those lovely Marshall vintage-look Bluetooth speakers and Cowshed products.
The hotel is only bookable by Members and Friends.
Book a stay at Soho House Chicago. Rooms from $240.
6. The Hoxton, Chicago
Bedrooms with a city view in downtown Chicago
The unstoppable London hotel group opened this, its third address in the US, in 2021 in the Fulton Market/West Loop former meat packing district.
It's got all the hallmarks we expect of the London-founded group: a laid-back, creative feel with a polished finish, décor that alludes to 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 be straight from the set of Mad Men.
In the rooftop bar, Cabra, gorgeous design details like rich green tile and deco lanterns are set to a backdrop of Chicago's skyscrapers thanks to the huge windows. The rooftop pool, studded with pastel pink tile and furnishings, also offers a fabulous view of the skyline.
Book a stay at The Hoxton, Chicago. Rooms from around $350.
7. The Gwen Hotel
The hotel is named after and inspired by Chicago-born abstract sculptor Gwen Lux (her work's well worth looking up, by the way). Lux's works features on the elegant facade and there's a general Art Deco aesthetic with plenty of curved lines and gold embellishments.
The luxury hotel is located on the upscaled "Magnificent Mile" and enjoys and excellent reputation, for its rooms and its rooftop bar and restaurant Upstairs at the Gwen.
All the rooms feature big windows looking out onto the Chicago skyline and are finished with chic yet comfy modernist furnishings and artworks that pay homage to Gwen Lux's style.
The hotel offers an "urban glamping experience" (pictured below), inviting guests to camp among the city's skyscrapers.
The in-house Italian restaurant Nico Osteria is a favorite with local and visiting foodies.
Book a stay at The Gwen Hotel. Rooms from $500
8. Thompson Chicago
The aspirational yet cozy Thompson Hotel is located in one of the smartest parts of Chicago in the Gold Coast neighborhood.
Design respects the classic Art Deco feel of the building, with modernist art features and plenty of curved lines in the furnishings, but it's far from fusty. There's wall prints from Joe Perez and and the much-loved subway tile 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 "rough luxury".
Book a stay at Thompson Chicago. Rooms from $300.
