The Best Hotels to Book in Illinois

Chicago Athletic Association has the feel of a gentlemen's club, with leather armchairs and sporting trophies galore
Chicago Athletic Association has the feel of a gentlemen's club, with leather armchairs and sporting trophies galore | Courtesy of Chicago Athletic Association / Expedia
Photo of Joe Bindloss
7 October 2021

There’s more to Illinois than the Windy City, of course, but coming here without visiting Chicago would be like going to Paris and skipping the Eiffel Tower. The vast expanse of Lake Michigan lends a seaside feel to the mightiest metropolis in the Midwest, and cultured museums and green-fingered parks are tucked in among the soaring skyscrapers of downtown. Stay downtown if you can, or try the inner suburbs just outside the CBD, home to the best bars and eats in the city. Here are the best hotels in Illinois – bookable on Culture Trip.

The Publishing House Bed and Breakfast

Bed and Breakfast
Courtesy of the Publishing House Bed and Breakfast / Expedia
An effortlessly cool revamp of a turn-of-the-century publishing house, this sophisticated B&B delivers a generous serving of industrial chic. Polished concrete and exposed steel rub up against Ottoman rugs, old timber floors and buffed-up workshop chairs. Provocative artworks share wall space with steer skulls and antique glass mirrors. Then there’s the Fulton Market location, which puts you just across the North Shore Channel from the Loop, with skyscraper views.
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Chicago Athletic Association

Boutique Hotel, Hotel
4.5/5 (964 Reviews)
Courtesy of Chicago Athletic Association / Expedia
Price Drop
Now from $205 per night
Is this a hotel, or a club for gents in top hats, teleported from the 1890s? The Chicago Athletic Association reclines lavishly behind a gothic facade facing Millennium Park, just yards from the Art Institute and pretty much everything else downtown. Inside, it’s all marble stairways, time-worn bookshelves, leather armchairs and sporting trophies. Rooms with vintage-inspired furniture make playful nods to the sporting past of the building – pommel horse for your clothes, anyone? What’s more, there are seven – yes, seven – places to eat and drink here.
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Freehand Chicago

Boutique Hotel
4.1/5 (1327 Reviews)
Courtesy of Freehand Chicago / Expedia
Price Drop
Now from $107 per night
You’ll know there’s something bohemian about the Freehand as soon as you see the frontage, with its hand-scrawled nameplate and vintage theater vibes. The bar and restaurant are crammed with old-fashioned wallpaper and tiki bar ornaments, and rooms and suites are full of mismatched details – coat-of-arms fireplaces, textured throw cushions, geometric rugs, mid-century sideboards – that somehow work seamlessly together as a whole. It’s irreverent, atmospheric and a whole lot of fun.
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The Guesthouse Hotel

Bed and Breakfast
4.8/5 (140 Reviews)
Courtesy of the Guesthouse Hotel / Expedia
Price Drop
Now from $238 per night
Being near the lake and close to green spaces are the must-haves for North Chicago, and this relaxing suburban hotel ticks both boxes. Facing the sprawling St Boniface Cemetery, the hotel is within walking distance of a string of lake shore parks and beaches, and has a calm roof terrace that will lift you up above the city streets. There are suites with one to three bedrooms, great for families and for those who like to be self-sufficient, with kitchens, breakfast bars and private balconies with gas barbecues.
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Thompson Chicago

Chain Hotel, Luxury
4.7/5 (962 Reviews)
Courtesy of Thompson Chicago / Expedia
Price Drop
Now from $189 per night
With a lavish lobby full of two-tone brickwork, convex mirrors and sultry lighting, the Thompson Chicago is the downtown dream, and the Near North Side location puts you within strolling distance of good eating and drinking and the sands of Oak Street Beach, just a block from the soaring steelwork of the John Hancock Center. It’s all about the views in the creatively themed rooms, with line-drawn artworks and huge windows framing sections of the Chicago skyline, lake shore and city lights.
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4.6/5 (944 Reviews)
Courtesy of Staypineapple /
Price Drop
Now from $113 per night
Firstly, consider the location of Staypineapple, circled by the Loop. It’s two blocks to City Hall in one direction, and two blocks to Millennium Park in the other. Go two blocks north and you hit the Chicago Theatre; go two blocks southeast and you’ll reach the official start of Route 66. Floor space comes at a premium this close to the action, but rooms at Staypineapple are comfy and calm, with Keurig coffee-makers and views over a swathe of glass towers.
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  • Hotel Arista

    Boutique Hotel, Hotel
    4.7/5 (961 Reviews)
    Hotel Arista
    Courtesy of Hotel Arista /
    Price Drop
    Now from $175 per night
    If you absolutely must be downtown, the Naperville setting might push the Hotel Arista off your shortlist, but there are perks to the Illinois tech corridor location. This sleek modern block rises above the CityGate campus, putting eating, drinking and live music within easy reach, and nearby, the I-88 running west to Iowa meets the I-55 running south to St Louis. It’s an inviting stop, with a full-service spa and big rooms with large windows to let in the light.
    More info

    Sophy Hyde Park

    Boutique Hotel
    4.8/5 (430 Reviews)
    Courtesy of Sophy Hyde Park / Expedia
    Price Drop
    Now from $200 per night
    Everyone clamors for the center, but there’s life south of the Loop, with plenty going on around the University of Chicago campus and Jackson and Washington parks. Stay at the Sophy Hyde Park and you’ll detect a tangible student buzz, with the lake shore right on the doorstep. Artsy murals and framed artworks splash color around the rooms – even in the bathrooms – and Metra trains zip north to the Loop and south to the Museum of Science and Industry.
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    Virgin Hotels Chicago

    4.6/5 (1204 Reviews)
    Virgin Hotels Chicago
    Courtesy of Virgin Hotels Chicago / Expedia
    Price Drop
    Now from $180 per night
    Edging into the Loop just below the Chicago River, this downtown hotel is walking distance from pretty much everything, from the Chicago Theatre to Millennium Park and the Art Institute – in other words, you’ll have culture on tap here. Sure, the hotel isn’t shy about putting Virgin branding on display, but the chambers – rooms, to you and me – have a calm maturity, with vaguely Nordic lines, downtown views and Tube logo rugs hinting at the brand’s British roots.
    More info
    These recommendations were updated on October 7, 2021 to keep your travel plans fresh. This article is an updated version of a story created by Joe Bindloss

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