One Life Kitchen

Top Five Favorite Chicago Rooftops

Chicago is well known for beautiful summer days. With epic views the city rooftops create for some of summer’s most happening moments. With only so many summer days and so many awesome rooftops, I am sharing in today’s blog some rooftop recommendations that I think you must hit up this summer. 


On the rooftop of the Chicago Athletic Association is where you will find Cindy’s. The high energy, hip rooftop has views of Millennial Park, the water of lake Michigan and City landscape. The rooftop offers its patron’s a variety of eating options. From little bites to go with your favorite cocktail to a full-on dinner menu and yes even brunch (cause in the city brunch is absolutely the best meal of the day) anytime of the day is a great time to be at Cindy’s. Known for being one of the more favorite Chicago rooftops, you will find this place is filled with a lively active nightlife. The Causal sit-down dining during the peak season will require a reservation. I have enjoyed quite a number of summer night’s here at Cindy’s and if you too are the social extrovert, I’m certain you will as well.


A Tourist dream rooftop is located at Navy Pier. This opened in 2019 and is the world’s largest rooftop. The views of Lake Michigan and the city skyline are priceless! The rooftop offers both a full-service bar and dining menu. Offshore as described on their site is 36K square feet with an additional 20k of terrace and 7 firepits

Being a Chicago resident, I personally avoid the tourist trap of Navy Pier, but I had to check this one out when I had CA friends visiting me. Offshore is located at the very end of the pier – yes making for quite a walk. While I personally don’t find this ideal for an average weeknight of rooftop drinking, I would absolutely recommend checking this rooftop out when you have a guest visiting in-town or when looking for something fun to do during a summer weekend.


Like Trump or not this glam rooftop in Trump tower is exquisite in every way. Whether it be the views of the river running through the city or the legendary Wrigley Clock Tower, this rooftop makes for a perfect photo-op. Trump terrace offers both a full bar and dinner menu. With a very generous square footage this rooftop provides a space of intimacy for both large and small gatherings. The service is excellent, the space is luxurious, and that high standard is carried all the way down to the luxardo cherry that tops off your cocktail. 

One of the more personal reasons I enjoy coming here often is because Terrace 16 is in the heart of downtown walking and it makes for a very quick and comfortably safe walk home.  While I have so many fond memories here, a favorite recent was on a beautiful Friday afternoon this past May with a group of my girlfriends. Chicago is exceptionally easy to show-off to my suburban friends when I bring them to Terrace 16 


Chicago club is the oldest private club in Chicago. In order to catch these rooftop terrace views you must be a member or know a member. If you are fortunate to visit this terrace, I am telling you this will turn out to be a summer memory of a lifetime! The views of Buckingham Fountain, Soldier Field, the water of Lake Michigan and the city scape when paired with their incredibly delicious food and service is truly something that is unmatched! The Club rooftop offers both a full bar menu and full-service dinner. There are several firepits and outdoor couches for intimate gatherings as well as a fireplace. The Chicago Club brings a respect to the city dining experience with its high-class service and required dress-code.  This rooftop makes also for an exceptional place to host a private party as I experienced first-hand when we celebrated my husband Sean’s 50th in June of this year.


Being one of Chicago’s most popular summer hangouts, I probably don’t have to share too much detail about what makes this tri-level rooftop such a happening summer hot spot. London House is located on Waker Drive in the heart of downtown. To say the views are incredible would be an understatement. Pretty much every direction you turn their amazing! I would highly recommend if you are visiting Chicago (or are in town on business) to stay at London House. It is a well-respected hotel and many of their guests will enjoy a business dinner in their restaurant followed by an after drink on the rooftop. 

Being a favorite to Chicago, this rooftop will get very busy during the summer months – especially on weekends. The vibe of the crowd definitely makes this high energy setting one that will require a reservation if you want to be seated. The rooftop itself offers a full bar and the bar menu is geared more as bite-size appetizers as their full menu is found in their indoor dining restaurant. I personally enjoy ending a summer day with a nightcap on this rooftop. Last time I was up here was right as summer was coming to an end. The city was looking so beautiful that I had to snap a photo to preserve my thought on how Chicago during the summer months is truly is a dream playground.

There is nothing like a summer memory in Chicago to hold onto during those cold bitter winter months. I hope in sharing my favorite rooftops, you will not only make a summer memory, but it will provide for you a guidance to a great rooftop to visit when in the Windy City. I would strongly encourage you during the high peak summer season to call ahead of time to make a reservation as is required for most outdoor dining/rooftopsj in Chicago.

linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram