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Chicago's Best Rooftop Bars for Spring

Posted on April 30, 2025   |   Updated on September 30, 2025
Adrian González

Adrian González

Person with blue fingernails and silver bracelet pours orange cocktail in glass. Rooftop view of a neighborhood in the background.

The Skyline cocktail at Up Room. (Photo by Tess Graham)

Warmer days are here, so we’re sharing the best Chicago rooftops to soak up the spring sunshine.

Up Room and Solana | Wicker Park

Atop the Robey Hotel is a two-fer. On the 13th floor, Up Room offers an updated spring cocktail menu, panoramic city views, and both indoor and outdoor seating. Meanwhile, a few floors below, Solana brings the party vibes. Solana opens officially on May 5, replacing the neighborhood favorite Cabana Club — but don’t worry, the space retains Wicker Park’s only public pool. It’s low-key but legendary.

Cerise Rooftop | Downtown

Head to the Virgin Hotel for sunset drinks and dancing at “the cherry on top,” a cocktail lounge on the 26th floor with a great rotation of DJs and social events.

Newsletter editor Emmi Mack at Offshore Rooftop. Wingspan for scale. (Photo by Cori Dahl)

Newsletter editor Emmi Mack at Offshore Rooftop. Wingspan for scale. (Photo by Cori Dahl)

The world’s largest rooftop bar is, in fact, at Navy Pier, according to Guinness World Records, measuring in at over 50,000 square feet. However, note that the majority is enclosed. Still, the glass ceiling lends an airy feel that’s worth a stop if you’re already at the Pier. You can also step onto a smaller outdoor patio for scenic pics if you really want to indulge your inner tourist.

The Woodland | Avalon Park

This beautiful community space has phenomenal food, a large event space, and a rooftop with immaculate vibes. It’s the perfect place to eat, drink, and vibe.

Open Outcry Brewing | Morgan Park

The beer and cocktail selection continues to expand, plus the pizza is killer and they prioritize fresh ingredients in their food. Full rooftop service doesn’t begin until later in the season, but you can take your drinks upstairs and start enjoying the sunshine.

Did we miss your favorite rooftop bar? Let us know!

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