Top 10: the best Chicago hotels with rooftop bars
An expert guide to the best Chicago hotels with rooftop bars, featuring the top spots for innovative cocktails, live DJs, swimming pools and incredible city and river views, near the Millennium Pier, Navy Pier, Shedd Aquarium and Art Institute of Chicago.
LondonHouse Chicago
Chicago, Illinois, United States
9Telegraph expert rating
It’s all about the rooftop LH on 22, which gives Instagram-worthy views of the Chicago River, Lake Michigan and the city’s skyline. The menu includes creative craft cocktails like the Roaring Twenties (strawberry, jasmine tea and champagne) and eclectic seafood-leaning selections. Standouts are the smoked arctic char, cold smoked salmon tartare and burrata salad. After spending the evening drinking in the views, wind down in one of the luxurious bedrooms with shimmery fabrics, funky light fixtures and marble-topped furnishings. Bathrooms have roomy walk-in showers and top-of-the-line bath amenities, along with a bath pouf. Read expert review From £89per night Check availability Rates provided by Booking.com
The Robey
Chicago, Illinois, United States
8Telegraph expert rating
When the weather warms, three words will be at play in the Wicker Park neighbourhood: double rooftop access. At the Robey, the 13th floor indoor-outdoor swanky rooftop lounge, Up & Up, gives way to remarkable views of the Chicago skyline, about four miles northeast. While its adjoining sister property, The Hollander, is home to a sixth-floor, indoor-outdoor rooftop lounge, with two bars and even a small, triangular dipping pool. The Robey is housed in a Twenties office building and vintage touches remain, from the preserved first-floor office directory to the etched Art Deco lifts. Natural light fills the bedrooms and the distant views of the city are worth the price of admission. Read expert review From £118per night Check availability Rates provided by Booking.com
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theWit Hotel
Chicago, Illinois, United States
8Telegraph expert rating
A kinetic energy buzzes through theWit, where the atrium-style glassed-in lobby looks out on the passing El train, and a nightclub-like vibe permeates the property all the way up to ROOF, the 27th floor bar. The rooftop also manages to glow an iridescent orange under the clubby pink lights. In summer, this open-air spot is perennially packed, and the sweeping views are well worth a $20/£16 glass of cabernet. The vistas continue in the bedrooms, with floor-to-ceiling windows that look across Chicago’s cityscape, river and lake. Beds are also comfortable, and the spa-inspired bathrooms have tasteful mosaic brown tile work. The fifth floor is home to a small gym with excellent views (and a yoga studio), as well as a spa. Read expert review From £72per night Check availability Rates provided by Booking.com
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Conrad Chicago
Chicago, Illinois, United States
9Telegraph expert rating
Bapiste & Bottle rooftop bar, located on the 20th floor, is bursting with bourbon-fueled energy. It serves 75 different whiskies and excels at classic cocktails (the Sazerac is divine) as well as more dramatic incarnations: the beverage director can be spotted pushing around a cart and creating Instagram-worthy drinks with flames and smoke (the Curtsey and a Bow, $25/£20 made with Basil Hayden 8 Year, orgeat and absinthe, served enshrouded in fog, doubles as entertainment). The bedrooms here are quite large, with warm earth tones, cushy orange coaches and enormous TVs. Read expert review From £181per night Check availability Rates provided by Booking.com
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The Godfrey Hotel Chicago
Chicago, Illinois, United States
8Telegraph expert rating
Its IO Rooftop Lounge (actually on a fourth-floor terrace, somewhat strangely) is the star, thanks to its glass ceiling and walls that retract. By day, locals come to gawk at the skyline view over beers and nibbles such as duck quesadillas. At night the music cranks up a notch, and club-going types wait behind a velvet rope to enter. The slate- and cocoa-coloured bedrooms here are unusually large, with mod-industrial touches like framed photos of gears on the walls. There's space enough for a plump king bed, wet bar, giant television, an ergonomic chair and desk, and a plum-hued lounge chair. Read expert review From £80per night Check availability Rates provided by Booking.com
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Virgin Hotel Chicago
Chicago, Illinois, United States
9Telegraph expert rating
It’s like a law of physics: when the weather is warm, Cerise is packed. The indoor/outdoor rooftop bar and nightclub has that uber cool, bold and splashy Virgin sensibility, drawing a particularly hip crowd. It’s all complemented by creative cocktails, DJs and panoramic 26th-floor views. There’s something mischievous about this hotel’s general feel; cue the Shag Room adjoining the bar ("it’s because of the carpet"). Virgin say they’re actively targeting female travellers and the bedrooms include well-lit theatre-style dressing tables, his and hers closets and a free yoga mat. Read expert review From £97per night Check availability Rates provided by Booking.com
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Soho House Chicago
Chicago, Illinois, United States
8Telegraph expert rating
It doesn’t get much better than a rooftop pool in the summer in Chicago, and at this indoor-outdoor lounge in the West Loop open only to overnight guests and members, there’s a whiff of giddy exclusivity. The sixth-floor perch is home to a pizza oven, bar, comfy daybeds, cosy outdoor fireplaces and, of course, glorious skyline views. This place brilliantly manages to never actually feel like a hotel. It’s more like you lucked into staying at your coolest friend’s city apartment, which happens to have an enormous gym with a boxing ring, spa and cinema. Each bedroom has that swanky apartment feel, with wood floors and vintage furnishings, along with modern touches like Nespresso machines. Read expert review From £322per night Check availability Rates provided by Mr & Mrs Smith
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Chicago Athletic Association Hotel
Chicago, Illinois, United States
9Telegraph expert rating
Buzzy rooftop spot Cindy's lends fantastic views, but people also flock for the food; the kitchen here serves lamb burgers, buttermilk-fried pheasant and other modern American fare, as well as posh cocktails. It's open for lunch, dinner and weekend brunch in a rustic-chic space with vaulted glass ceiling and awesome views of Millennium Park. The hotel itself is all dark wood, leather and retro-clubby public areas where whiskey glasses clink. It's in the thick of downtown's action — ace for business travellers and power sightseers. Playful touches like the Game Room keep things from getting too stuffy. Read expert review From £121per night Check availability Rates provided by Booking.com
Loews Chicago Hotel
Chicago, Illinois, United States
9Telegraph expert rating
'Sprawling' isn’t usually a word that applies to rooftops, but it applies here. The third-floor terrace at Loews is so large (it’s the biggest in Chicago), it feels like a city park, complete with trees, flowers, grassy spaces for lawn games, two bars and Steeterville Social, a restaurant that serves globally inspired small plates. Views peer up at surrounding buildings and out to Navy Pier and Lake Michigan. Other attractions here include an indoor lap pool and mini spa with treatment rooms for massages and facials. The casual-contemporary rooms are quite large. Blackout blinds are a welcome amenity. Especially after a heavy night on the rooftop. Read expert review From £97per night Check availability Rates provided by Booking.com
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Hotel Lincoln
Chicago, Illinois, United States
8Telegraph expert rating
To understand how beautiful Chicago is, do as the locals do and head to The J. Parker on the 13th floor of Hotel Lincoln. The Lincoln Park rooftop gazes out at the deep blues of Lake Michigan, the white sands of North Avenue Beach and the lush greens of Lincoln Park. With a retractable roof, you can enjoy craft cocktails and snacks, rain or shine. Original, retro-cool design and kitschy fun are the hotel's hallmarks. Perks for guests include free pedicab (think rickshaw) rides to the nearby beach and zoo. Bedrooms have a groovy style with either checkered or zig-zag-print carpet and colourful modern paintings by local artists covering the earth-tone walls. Some have lake views. Read expert review From £81per night Check availability Rates provided by Booking.com
