The Best Rooftop Bars in Chicago

On the 13th floor of the Chicago Athletic Association hotel, Cindy's looks directly over Millennium Park and Grant Park to Lake Michigan beyond. The view is the best of any rooftop bar in Chicago: the Bean, the park, the lake, and the south side of the Loop in one frame. The cocktail menu is well-executed and the staff understand the bar's position as a destination rather than a neighbourhood spot. The outdoor terrace fills by 6pm on summer weekends.

Order: Chicago Style Old Fashioned with Widow Jane bourbon and a Luxardo cherry

On the 21st floor of the Peninsula Chicago, Z Bar looks north along Michigan Avenue and the Gold Coast, with the lake visible to the east through the gap between the towers. It is a more contained view than Cindy's but the quality of the experience is higher — better cocktails, better service, and a terrace that does not feel overrun on a Wednesday evening. The Peninsula's bar team knows what it is doing. The whiskey selection alone justifies the trip.

Order: Peninsula Manhattan with Knob Creek Single Barrel and Carpano Antica sweet vermouth

Raised Bar at the Renaissance Chicago occupies a north-facing terrace that looks over the Chicago River and the bridge district. It is a different orientation from the lake-facing bars but the river at night, with the bridges and the architecture on both banks lit up, is a view that holds its own. The cocktail program is modern American and better than hotel bars typically manage. The crowd skews business travel on weeknights and social on weekends.

Order: River North Gimlet with local FEW Spirits gin and house-made lime cordial

On the 16th floor of a River North tower, Spire 16 offers 360-degree views of the Chicago skyline that no hotel rooftop can match for sheer comprehensiveness. The full Loop to the south, the Gold Coast to the north, the river to the west, and a sliver of lake to the east. The cocktail program is solid and the bar does not take itself too seriously, which means the prices are slightly more reasonable than the view would suggest they need to be.

Order: Spire Mule with Koval Millet Whiskey, fresh ginger, and house ginger beer

The rooftop level of Nobu Chicago in the West Loop is a Japanese-inflected cocktail experience with city views that improve as the West Loop's skyline continues to fill in. The bar program here draws on the kitchen's influences — yuzu, shiso, Japanese whisky — and executes them without the gimmickry that destination cocktail bars sometimes mistake for creativity. Go Thursday evenings when the crowd is predominantly restaurant-industry and the bartenders have more time to talk.

Order: Shiso Gimlet with Nikka Coffey Gin, shiso simple syrup, and fresh yuzu

Wicker Park is where Chicago actually lives between the tourists and the corporate crowd, and Beacon Taproom Rooftop is the honest rooftop bar that neighbourhood deserves. The view is Wicker Park rooftops rather than the Loop, the beer selection is excellent, and the prices are what they should be. Local craft beer on tap, a food menu of above-average bar snacks, and a crowd of people who live within cycling distance. More enjoyable than 80 percent of the hotel rooftops on this list.

Order: Revolution Anti-Hero IPA on draft, the best local IPA in the city

Lincoln Park's rooftop bar sits above the neighbourhood's brownstones and tree canopy with a north-facing lake view that most visitors never discover. The crowd is predominantly local — the kind of residents who moved to Lincoln Park specifically to avoid the hotel-bar circuit. The cocktail program is serious without being pretentious. The chef-driven bar snacks are better than the bar needs them to be and considerably better than the menu price suggests.

Order: Lakeside Negroni with Three Dogs Run Gin, Carpano Bianco, and local cherry bitters

The Old Post Office conversion is the most dramatic piece of adaptive reuse in Chicago's recent history, and the rooftop occupies the enormous terrace above the old sorting floor with views down the length of the Chicago River toward the Loop. It is a context that no purpose-built hotel rooftop can manufacture. The bar program is cocktail-forward and rotating. The wind can make open sections uncomfortable — note the enclosed sections for the cooler months.

Order: Chicago River Sour, a rye whiskey and apple cider shrub cocktail with house barrel bitters

Harriet's at the 21c Museum Hotel brings the art hotel concept to Chicago's West Loop rooftop, which means the design is genuinely interesting rather than decorative. The contemporary art installations change quarterly, the cocktail program is developed by a serious bar team, and the crowd is creative-professional rather than financial-professional. Best on Thursday evenings during summer when the gallery stays open late and the terrace catches the last of the western light.

Order: The Curator, a lavender and honey gin cocktail with edible flower garnish

Three Dots and a Dash is primarily a subterranean tiki bar, but the summer terrace above it operates as a genuine rooftop with city views and the full rum-forward cocktail menu available outdoors. The tiki tradition is taken seriously here — proper rums, proper citrus, proper ice. It is the most fun rooftop bar in Chicago during the summer months, with a crowd that has made a deliberate choice to be there rather than defaulting to the nearest hotel terrace.

Order: Three Dots and a Dash signature, a three-rum blend with allspice dram and lime served in a tiki mug