Rooftop Bars We’re Raving About in Chicago

Chicago may be known as the Second City, but their rooftop bar game is second to none. Home to four of the top 10 tallest buildings in the United States, you can’t beat the skyline views from a rooftop bar in Chicago.

Despite their relatively short summer season, if you find yourself breezing through the Windy City on a warm summer night you’ll have no shortage of rooftop bars and beer-gardens to choose from.

With more than 60 different rooftop bars, we’ve compiled a list of the top 3 to visit this summer in Chicago. So sit back, sip some wine, and prepare to watch the sunset over the city, because we’ve got the inside scoop on the best rooftop bars Chicago has to offer!



Photo: Apogee

Located 26 stories up, in Chicago’s River North neighborhood, Apogee offers panoramic city views. Of course, gorgeous views are great, but you know we’re all about the drinks.

Apogee is known for their whimsical approach to mixology, whipping up craft cocktails that look like something from a Tim Burton movie on the daily. Thankfully, their seasonal rooftop is no exception to their Alice in Wonderland approach to crafting cocktails.

Drink Recommendations

If you’re ordering a single cocktail on a hot summer night, we suggest keeping cool with an Apogee Frose (Frozen Rose, Aperol, St. Germain, Raspberry). If you heading out with friends, we suggest trying one of Apogee’s ‘large format’ drinks, like the Mr. Nice Guy (Absolut Elyx Vodka, Hop Smoke, Ginger, Pineapple).



Photo: Chicago Athletic Association

Although the skyline is impressive, there’s so much more to see in the city, and Cindy’s has a view of it all. With amazing views of Lake Michigan, Millennium Park, and Chicago’s iconic Bean, Cindy’s city views are tough to beat.

Drink Recommendations

If you’re looking for something refreshing to sip this summer, we suggest their Leila Elixir (Tito’s Handmade Vodka, cocchi americano, emperor’s chamomile, lemon, cucumber, peychaud’s).

The Robey (Cabana Club)


Photo: The Robey

Escape the hustle and bustle of downtown and soak up some real city vibes at the Robey in Chicago’s vibrant Wicker Park neighborhood. The Cabana Club is nestled atop the 6th floor of The Robey hotel, and is one of the few rooftop bars located outside of downtown. Bonus, if you’re a guest at the hotel, you also have access to the rooftop pool located in the Cabana Club!

Drink Recommendations

Nothing beats a frozen cocktail on a hot summer day, and the Cabana Club has a variety to choose from. We suggest a Basil Gimlet, perfect for sipping while soaking up 180 degree views of Chicago’s skyline.

Hit the Rooftop

Now that you know all the hottest rooftop bars in Chicago, you’re ready to hit the roof… soon. I mean, not tonight obviously. Tonight’s more of a sip wine on the couch and watch Netflix kind of night. You know how it is.

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