Photo Credit: Plymouth Restaurant & Rooftop Bar
Photo Credit: Plymouth Restaurant & Rooftop Bar

Chicago has one of the most beautiful skylines of any city in the country, so why not take it all in while grabbing a drink or enjoying a meal? We’ve put together a list of 8 of the best rooftop restaurants and bars in the city:

Photo Credit: Cindy’s


12 S Michigan Ave, Chicago, IL

Quite possibly one of the best rooftops in the city of Chicago, Cindy’s is undoubtedly a fantastic spot for any occasion. This hip, stylish spot is a guaranteed hit with anyone who visits. Located downtown in the Chicago Athletic Association Hotel, Cindy’s offers a selective yet unique menu that is guaranteed to send your taste buds on a journey. If you need a suggestion, we recommend the Smoked Whitefish Dip as a starter, followed by Jerk Chicken for the main dish. Of course, you can count on Cindy’s to have an incredible drink selection, too.

Plymouth Restaurant & Rooftop Bar

327 S Plymouth Ct, Chicago, IL

If you’re looking for a year-round rooftop with an extensive menu, look no further than Plymouth Restaurant & Rooftop Bar. Located in the Loop, this classic spot offers a wide variety of sandwiches and burgers, pairing perfectly with their long list of beers, cocktails and liquors. The three-level restaurant in Chicago is perfect for any occasion. Not sure what to get? You can never go wrong with the Fish Tacos paired with a Bells 2 Hearted Ale.

Photo Credit: LondonHouse Rooftop

LondonHouse Rooftop

85 East Wacker Drive At, N Michigan Ave, Chicago, IL

This chic, upscale spot with indoor and outdoor seating is a classic in the Chicago area. Located in LondonHouse downtown, close to the Magnificent Mile, the rooftop has one of the most picturesque views of the city. You’ll get to enjoy your meal or a drink while fully immersing yourself in everything that downtown Chicago has to offer. We suggest the Lobster Biscuits and Gravy, without a doubt.


203 N Wabash Ave 26th floor, Chicago, IL

Located in Virgin Hotels Chicago, this hip venue is a great spot for a night out. Offering drinks and dancing, all while enjoying breathtaking views of the city, Cerise provides everything you need for a fantastic night on the town with your friends. Luckily, this place isn’t just for the nightlife. They also have a dining menu with American fare classics that are guaranteed to satisfy your cravings.

Photo Credit: RAISED


1 W Wacker Dr, Chicago, IL

This urban rooftop bar located right along the river is a dream location for many. Providing creative cocktails and exquisite small plates for a sophisticated time out, RAISED is sure to exceed any expectations. With the indoor and outdoor lounge-style seating, there’s no doubt you’ll be able to relax with your loved ones in this chic atmosphere. Try the Scarlet Begonias cocktail. You can thank us later.

Streeterville Social

455 N Park Dr, Chicago, IL

Located in the Loews Chicago Hotel, Streeterville Social is a stunning spot featuring elevated menu options and unique cocktails to match. The urban landscape is a great way for you to dive into the city, all while enjoying dishes that make your mouth water with every bite. We recommend the Mini Lobster Rolls to eat with the Sweet Dreams cocktail. 

Photo Credit: Cabana Club

Cabana Club

2018 W North Ave, Chicago, IL

Located on top of The Robey in Wicker Park, Cabana Club has a mix of everything. With their unique selection of cocktails, light fare and urban atmosphere, there really is something for everyone here. They even have a guests-only pool, but feel free to sunbathe on the rooftop while enjoying a drink if you’re just stopping by!


2 W Erie St, Chicago, IL

Sitting atop the Dana Hotel and Spa downtown, Apogee is a River North hot spot for all things drinks and dancing. Hosting DJs, serving creative cocktails (including their infamous Bong Drink) and providing a venue space, Apogee has got it all. Conde Nast Traveler rated this spot one of the Best Rooftop Bars in 2018. Still not convinced? Go check it out for yourself and you’ll be quick to understand the hype.

With so many rooftop spots to choose from, it can be hard to narrow down the list to just 8 choices. Didn’t see your favorite rooftop on our list? Drop us a comment below with other suggestions!

Author Bio: Lydia Matteoni is an avid plant lover, cat mom, and self-declared Twitter addict. After moving from Pittsburgh to Chicago in 2018, she decided to fully immerse herself in Chicago culture, more specifically, in music and the arts.

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