The Top 10 Rooftops and Terraces in Chicago to See This Summer

These rooftops and terraces should be at the top of your must-see list this season.

The city of Chicago in the summertime is almost an entirely different city with a lighter, happier, more relaxed state of mind. Beach days, outdoor festivals and concerts and rooftop terraces dominate the summer social scene. And these top ten rooftops and terraces won’t disappoint any visitorwhether it’s for the food, drink or views. It’s best to put every single one on your summer bucket list.

1. Cindy’s Rooftop

As a part of the Chicago Athletic Association, Cindy’s Rooftop restaurant and open-air terrace tops most Chicagoans’ must-see lists due to its stunning views of the city’s treasured Millennium Park, Lake Michigan and beyond. “Cindy’s unique view makes it different from other rooftops in Chicago. With a design aesthetic reminiscent of a Great Lakes beach house, the open-air terrace serves as the front porch to the city – opening to the sweeping vista,” said a spokesperson from the restaurant.

Try out one of the inventive cocktails from Spirit Guide Nandini Khaund, including 4 different rosés curated by Sommelier Sterling Knight, and two homemade popsicles (one with booze) from Executive Pastry Chef Jove Hubbard.

2. Joy District

Looking for a cool vibe for your next round of drinks? The rooftop deck at Joy District Chicago could be the spot. This New American restaurant and cocktail bar in the River North neighborhood has a comfortable rooftop lounge and late-night dancing if you’re up for it.

Murals line the place inside and out while menu items like Tuna Poke Cones and Smoked Pork Spare Rib Lollipops help the menu stand out from the norm. If you’re looking for a quiet night, this is not the place to go as loud music keeps the crowd dancing and drinking throughout the night.

3. Cerise Rooftop at the Virgin Hotel

At Cerise rooftop bar, you can “discover a new point of view.” In the heart of the Loop in Chicago you’ll find this cocktail lounge and dance club on the 26th floor of the Virgin Hotel. A casual chic vibe with city skyline views, this rooftop could be the place to start your night or hang out with friends. Enjoy music from live DJs or sip craft cocktails as you enjoy the view.

4. RAISED | An Urban Rooftop Bar

Going on its second summer and year in business, RAISED prides itself on its relaxed and laid back atmosphere while still providing an unforgettable dining and drinking experience. “It’s a fun place to come visit and while we take our cocktails, wine and beer super seriously, we like to have fun with our customers,” said Bill Nykaza, Bar Operations Manager.

As far as which cocktails to try, Nykaza suggests the Watered Flowers and Summerhouse Cigar as the top two on his list. You can also sip on one of their draft wines or local beers that must be brewed in the city of Chicago or the surrounding area. Don’t forget to get there early on a typical night, as the open rooftop is first come first serve, just like any beer garden.

5. The J. Parker

On a beautiful Chicago summer day, this bar is one that should be high up on your list. The J. Parker sits on top of the Lincoln Hotel in Chicago’s Old Town neighborhood with unobstructed views of Lake Michigan. Sip on one of their Signature Cocktails, craft beers or wine while taking in the view in the lounge’s comfortable seating. Try brunch from 9 a.m. - 2 p.m. on Saturdays and Sundays.

6. Homestead on the Roof

From walking by, you may not see this cozy rooftop spot. This seasonal farm-fresh restaurant hides above Roots Handmade Pizza in Chicago’s West Town neighborhood. The rooftop patio restaurant also has a small production of wines, a weekly rotating craft brewery and a 100-bottle spirits list as part of their beverage program. The cozy restaurant serves farm to table fare with seasonal ingredients and dishes ranging from gazpacho, to foie gras to seafood paella. Stop by on a warm night for delicious food, desserts and drinks.

7. Drumbar

On the 18th floor of the Raffaelo Hotel, you will find the speak-easy style bar and rooftop, named Drumbar. With views of the Chicago’s Gold Coast neighborhood, Lake Michigan and the Hancock Building, you can sip exciting cocktails in the comfortable lounge area complete with fire pits. “Upon entering the space, a decadent interior lounge area makes way to a 1,500-square foot rooftop terrace, offering built-in lounge seating, two fireplaces and panoramic views of the lake and city,” said Jamie Gray, PR Manager for Drumbar. Gray also recommends the Bolivia cocktail from Drumbar’s new Around the World menu made with Singani 63, olive oil, lemon, pineapple, cumin, egg white and garnished with black pepper.

8. Gene’s Sausage Shop

In 1972, Gene’s Sausage Shop opened as a small neighborhood deli specializing in homemade smoked sausage and Polish delicacies. When the shop opened in a new location in Lincoln Square, they were able to add its Rooftop Beer & Wine Garden. Dine and drink with friends at communal wooden tables in the European atmosphere next to flowers, tomatoes, herbs and grapes. Get something fresh off the grill or poured from the skylight bar once this rooftop opens after Memorial Day weekend each year.

9. IO Godfrey Lounge at the Godfrey Hotel

This urban roofscape is found on the fourth floor of the Godfrey Hotel in the middle of River North with uninterrupted views of the city’s southern skyline. Named with “IO” for its captivating indoor and outdoor ambiance, the rooftop takes up 15,000 square feet and has a retractable roof to enjoy the space during all types of Chicago weather.

10. The Robey

High above Wicker Park’s busiest corner at Milwaukee, Damen and North Avenue sits the Robey Hotel. This stunning rooftop lounge is located on the 13th floor of one of the highest buildings in the area for miles providing breathtaking views. What makes this rooftop even more unique is that it boasts a beautiful rooftop pool providing an oasis vibe perfect for summer in the city. Cool off from the heat with a cocktail and a dip in the pool.