Chicago · Rooftop bars
Best Rooftop Bars in Chicago for Grown-Ups
Chicago's rooftops are at their best from May to September, but the good ones keep going with heaters, fire pits and glass rooms well into autumn. These are the five we would pick for a drink with a view, grouped by the part of town you will be in anyway.
- Best view of the park and lake
- Cindy's
- Best for the river
- LH Rooftop
- Highest
- CloudBar at 360 CHICAGO (94th floor)
- Best for dinner
- Cabra, West Loop
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In the Loop, on the lake side
If you only have one rooftop evening, make it Cindy's. It sits on the 13th floor of the Chicago Athletic Association, directly across Michigan Avenue from Millennium Park, and it has a glass-roofed room as well as the terrace, so it works in shoulder season too. LH Rooftop on the LondonHouse hotel is a five-minute walk north, on the Michigan Avenue bridge: three levels of terrace facing the river, the Wrigley Building and the lake. Go in the late afternoon, before the after-work crowd.
Cindy's
Chicago Athletic Association, 12 S. Michigan Ave
A 13th-floor glass-atrium restaurant and terrace looking over Millennium Park and the lake. Fire pits in winter, open-air seats in summer.
LH Rooftop
LondonHouse, Michigan Ave bridge
A tri-level rooftop above the Michigan Avenue bridge with river, lake and Magnificent Mile views. Busy in summer; lovely in the late afternoon.
Highest in the city
CloudBar is not a rooftop in the open-air sense: it is an 18-seat bar inside 360 CHICAGO, the observation deck on the 94th floor of the former John Hancock Center. You pay for deck entry, and in return you get the whole city and the lakeshore laid out below you. Time it for sunset and stay for the lights coming on.
360 CHICAGO and CloudBar
94th floor, 875 N. Michigan Ave
The 94th-floor observation deck in the former John Hancock Center, with an 18-seat CloudBar for a cocktail with the view. TILT, which leans you over the edge, is extra.
North of the river: Lincoln Park
The J. Parker on the 13th floor of Hotel Lincoln faces Lincoln Park and the lake, and it is calmer than the downtown rooftops on most weeknights. It pairs well with an early show at The Second City in Old Town, a short walk or ride away.
The J. Parker
Hotel Lincoln, 1816 N. Clark St (13th floor)
The rooftop bar on the 13th floor of Hotel Lincoln, with about 140 outdoor seats and a 55-seat indoor room looking over Lincoln Park, Lake Michigan and the skyline. The best rooftop north of the river, and a natural first stop before Second City or a Lincoln Park dinner.
Tip: Reservations are taken online; the outdoor seats go first on warm evenings.
The Second City
1616 N. Wells St, Old Town
The improv and sketch theatre that launched generations of comedians. The mainstage revue runs two shows on Friday and Saturday nights.
West Loop: a rooftop dinner
For a meal rather than a round of drinks, Cabra on top of The Hoxton is Stephanie Izard's Peruvian restaurant, with skyline views to the east. It is in the middle of the Randolph Street restaurant row, so it is also an easy pre-dinner drink before Girl & the Goat or Monteverde.
Cabra
The Hoxton, 200 N. Green St (rooftop)
Stephanie Izard's Peruvian rooftop restaurant and bar on top of The Hoxton, with West Loop skyline views and bright Peruvian plates and cocktails. Dinner nightly from 4 p.m., brunch on weekends, and a Sunday pool pass in season.
Tip: Happy hour runs Monday to Friday in the late afternoon; book dinner for sunset.
Tips for a rooftop evening
- Book when you can. Most Chicago rooftops take some reservations and keep some space for walk-ins; the walk-in seats vanish first on warm Friday and Saturday evenings.
- The wind off the lake can make a rooftop 10 degrees cooler than the street. Bring a layer, even in summer.
- Sunset is the best time for the view and usually the calmest hour before the late crowd arrives.
- Pair a rooftop with a river trip: the architecture cruise leaves from Wacker Drive, a short walk from LH Rooftop.
Everything here was checked in September 2026. Club line-ups, cruise seasons and performance calendars change, so confirm before you go.
Questions people ask
What is the best rooftop bar in Chicago?
For a first visit, Cindy's: it looks straight over Millennium Park to the lake and has a glass-covered room for cooler nights. LH Rooftop is the pick for river views.
What is the highest bar in Chicago?
CloudBar at 360 CHICAGO, on the 94th floor of the former John Hancock Center. Entry to the observation deck is required.
Are Chicago rooftop bars open in winter?
Some are. Cindy's has an enclosed glass room and fire pits, and The J. Parker has an indoor room. Open-air terraces are best from May to September.
Is there a rooftop restaurant in the West Loop?
Yes. Cabra, on the roof of The Hoxton at 200 N. Green St, serves Peruvian food with skyline views, dinner nightly and brunch on weekends.