4 Of The Best Chicago Rooftop Bars Revealed

Take in the views of Lake Michigan, the Chicago River, Lincoln Park.

J Parker Chicago Rooftop Bar

Whether your summer is spent working in a Chicago skyscraper, lying on the beaches of Lake Michigan, or being the coffee running intern you will eventually find yourself on one of Chicago’s many rooftop bars. This seems only appropriate in the city that invented the skyscraper to sit perched atop them to take in the views of Lake Michigan, the Chicago River, Lincoln Park all while sipping on some delicious cocktails.


12 S. Michigan Ave (Loop)

Cindy's Rooftop
FACEBOOK Cindy’s Rooftop

If you have ever spoken to someone about Chicago rooftop bars nine times out of ten, the first one that they’ll recommend is Cindy’s. On top of the Chicago Athletic Association Cindy’s holds one of the most picturesque views in the city. Overlooking Millennium Park, the modern wing of the Art Institute, as well as Lake Michigan its hard to see why people go to other rooftops. If you time it right you may even catch a Millennium Park concert from the terrace of Cindy’s in the summer or even cozy up next to a fire pit on chilly nights.

With such a gorgeous view comes loads of crowds. In the summer there is a line at the elevator to even get up to the roof and dinner reservations are required weeks and sometimes months in advance. Dinner is served more family style and booking a reservation is well worth it for this delicious food. If you want to try to sneak in at the last minute, try going to Cindy’s for lunch which is served 11-2 Monday – Friday. The downside of Cindy’s is that the large crowds have made the service begin to flounder. It becomes impossible for waiters and waitresses to navigate the crowded bar and expect any order to be at least a 15-minute wait. Everyone should go to Cindy’s for the view at least once. That said if you’re the type of person who expects good service then expect to be disappointed.

The J. Parker

1816 N. Clark St. (Lincoln Park)

The J. Parker
FACEBOOK The J. Parker

Rain or shine the J. Parker is there for a rooftop cocktail. Its retractable glass roof allows you to stay right at your hard earned seat even if it begins to sprinkle a little. Sitting on the 13th floor of the Hotel Lincoln, The J. Parker provides you with a more organic view of the city. Overlooking Lincoln Park, Lake Michigan, the Gold Coast and the city skyline provides the perfect after work relaxation spot. With 55 seats on the inside and 140 outside you may have to befriend the couple who just got their check to get them to give their seats to you but its well worth the wait.

The bar boasts its destination themed cocktails such as Lake Geneva, Ibiza, and Zanzibar. Some so exotic that the pronunciation is on the menu to avoid the awkward finger point when ordering. These themed cocktails are absolutely delicious and cover a wide range of flavors from tropical to spicy. The food menu is pretty minimal, but has something for everyone including a fried chicken sandwich, grilled cheese, and an incredible burger for large plates. So take a sip to another place an enjoy the view.


122 W. Monroe Street (Loop)

Boleo chicago

While Boleo doesn’t have an open-aired terrace its retractable glass roof provides views of the city skyline including the Willis Tower which lies just stories above. Atop the Kimpton Grey Hotel, this rooftop bar/restaurant serves Southern Hemisphere drinks paired with Peruvian street food. Upon entering the sleek lush design of Boleo you feel as if you have been transported to South America as you become engulfed into vibrant music. Boleo is perfect for a night of drinks and sharing small plates with a group of friends. The large dance floor lies just below the glass roof allowing you to dance the night away under the stars.


201 E. Delaware PL (Gold Coast)

Drumbar chicago
INSTAGRAM @drumbarchi

Drumbar holds several rooftop bar accolades including best whiskey bar and best rooftop bar in Chicago. Drumbar is best known for their extensive list of old fashioneds, but their rotating cocktail menu is absolutely delicious. The rooftop terrace is lined with couches around the perimeter paired with chairs surrounding the numerous fire pits. This speakeasy-style bar provides something for everyone from its intimate indoor lounge area to its cozy terrace.

From June 23 – September 1 every Saturday Drumbar is presenting a series entitled Summer Sounds 2018. This series includes performances of today’s top artists to raise funds and awareness for mentor health and minority mentorship costing $25 for general admission and $35 for VIP tickets. While I am all for supporting local movements I question how business is going for Drumbar as they’re implementing this new initiative and taking a weekend day out of the week for the crowd just looking for cocktails.

Emma Hoskins


Emma is a Chicago native currently studying environmental engineering at Carnegie Mellon. You can typically find her going on spontaneous road trips, eating good food or hiking.

Jetset Times in your inbox

Sign-up for our newsletter

By signing up, you agree to our Privacy Policy and European users agree to the data transfer policy.