In the summer, there’s nothing better than sitting on a rooftop and catching up with friends. I love going to different rooftops to try appetizers, people watch, get drinks, watch the sunset, and take in the views. Luckily, Chicago has a lot to offer, and no matter where you are in the city, you’re bound to be able to find a cute rooftop where you can unwind and relax. I’ve come up with a list of some of my favorite rooftops in Chi that each have something different to offer.

Cindy’s Rooftop

If you’re visiting and have to pick and choose which restaurants to hit, go to Cindy’s Rooftop. Nothing beats the incredible views of Millennium Park, Grant Park, and Lake Michigan—especially at sunset. It allows you to see some of the best parts of the entire city. To top it off, Cindy’s is fun, social, and full of young people and great food. And if you aren’t in the mood for drinks, do brunch instead—they added a full brunch menu just in time for the summer!

Little Goat

Little Goat is a cute little diner located in an up and coming, trendy neighborhood. It's in the hip area of the street with tons of fun restaurants and bars. The rooftop at Little Goat is perfect for casual drinks, a private party, or is even a great spot to enjoy a mimosa post brunch. 

Gibsons Italia

This swanky restaurant and bar has three levels of incredible city views. Each level has a different vibe—a normal "post work drinks" bar on the first floor, Italian restaurant on the second, and a rooftop bar on the third. After dinner, head up to the third floor for a good time! The music, drinks, strung lights, and open air bar make for the ultimate summer vibe.

London House

London House arguably has the best view on the Chicago River. It's located on the top floor of the London House Hotel and nothing beats the glowing city views at night. And, the place is always packed—especially during the summer.


3 Arts Cafe is a restaurant nestled in the center of a Restoration Hardware store in the Gold Coast neighborhood. No joke, this is the most aesthetically pleasing restaurant out there, trust me. With the marble tables, greenery, crystal chandeliers, open skylights, and a fountain in the center, you’re bound to get the best food pics. You also have to make sure to go upstairs to the rooftop garden. Although it’s kind of a hidden gem, its beautiful and has some pretty views. Since there is usually a long wait to get into 3 Arts, grab a latte from the coffee bar and head up to the rooftop with friends to enjoy your wait!

Wrigley Rooftops

It wouldn't be a Chicago post without a tribute to Wrigley. One of the best ways to enjoy a Cubs game is right from a rooftop which allows you to see the game, while preserving that fun bar, rooftop vibe. Any summer day at spent at Wrigley is certainly not a day wasted!

Next time you're in Chicago and looking for a fun time and good view, head to one of these rooftops—you certainly won't be disappointed!