The best hotels in Chicago, where fabulous design meets perfect rooftop pools

Book at stay at one of the best hotels in Chicago, from literary temples to a former belt factory but all with incredible decor

The rooftop pool at Hoxton, Chicago
(Image credit: Hoxton Chicago)

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 

An elegant sitting area in the Publishing House hotel

(Image credit: Anna Zajac)

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.

The Publishing House Hotel, Bellow bedroom

(Image credit: The Publishing House Hotel)

2. Chicago Athletic Association

Chicago Athletic

Old-school Americana glamor at the Cherry Circle bar

(Image credit: Chicago Athletic)

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.

Chicago Athletic

The décor strongly alludes to the building's past

(Image credit: Chicago Athletic)

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

(Image credit: 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 Robey

(Image credit: The Robey)

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

Freehand Chicago

(Image credit: 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

Freehand Chicago are evocative of retro train cabins

(Image credit: Freehand Chicago)

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

Soho House Chicago

One of the stylish bedrooms at Soho House Chicago

(Image credit: 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.

Soho House

The look is old-school but slinky

(Image credit: Soho House)

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

Hoxton Chicago bedroom

Bedrooms with a city view in downtown Chicago

(Image credit: Hoxton 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. 

The rooftop pool at Hoxton, Chicago

(Image credit: Hoxton Chicago)

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.

Hoxton Chicago

(Image credit: Hoxton Chicago)

7. The Gwen Hotel

Gwen Hotel suite

(Image credit: 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.

Gwen Hotel

(Image credit: Gwen Hotel camping)

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

Thompson Hotel

(Image credit: Thompson Hotel)

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.

Thompson Hotel

(Image credit: Thompson Hotel)

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.

Hannah Meltzer

Hannah Meltzer is a Londoner by birth and Parisian by adoption. She previously worked on the staff of The Daily Telegraph’s travel desk, before moving to Paris in 2017. She writes regularly about travel and Parisian culture for The Telegraph as an expert destination correspondent. She has also written for The Independent, The Times, Vanity Fair, openDemocracy and Télérama. Recently she wrote a podcast series about Parisian culture for an LA-based production company.

Hannah is based in the 18th arrondissement in the less touristy side of Montmartre behind the Sacré-Coeur basilica. Though her life sometimes resembles a hammy cliché — sketching in sidewalk terraces, walking her beloved dog Babette through the streets of Montmartre — she is adamant she has not lost her London humour and open-mindedness, or her accent.