14 Awesome Rooftops To Check Out In Chicago

Mª del Rosario Castro Díaz Mª del Rosario Castro Díaz

Chicago Rooftops

This year more than ever, summer calls for outdoor dining and gorgeous city views so we’ve put together a list of rooftops around Chicago you need to try right now!

From mouthwatering Mediterranean food and absolutely delectable Mexican slow-roasted meats with a side of refreshing margaritas to rooftop yoga with bottomless mimosas, these rooftops have it all (including safe social distancing guidelines)! Check out these 14 awesome Chicago spots below:


1. Aba, West Loop

Are you a fan of Mediterranean cuisine? Then we suggest checking out Aba. This low-key rooftop restaurant set in the historic Fulton Market District incorporates influences from across the Mediterranean including Israel, Lebanon, Turkey and Greece to create light and delectable dishes. Their bar menu also features rare Mediterranean-inspired wines and spirits. Our favorites are their whipped feta spread with crushed pistachios ($9.95) and the Chef’s special Khachapuri with cremini mushrooms and graviera ($13.95). Combine them with their Mediterranean Mule ($13) featuring herb-infused vodka and pistachio and you’ve got the perfect pairing!

You can find Aba at 302 N Green St. 


2. AIRE, The Loop

Journey 24 floors up through the Hyatt Hotel to enter this summer oasis known as the AIRE rooftop. Here you’ll find a wide seasonal array of handcrafted cocktails, shareable plates and local craft beers as well as the usual pop-ups by local businesses. In the past, AIRE has hosted pop-ups from Soulé and Scooped Cookie Dough Bar among others.


You can find AIRE at the Hyatt Hotel at 100 W Monroe St. 

3. Cindy’s, The Loop

With its glass-vaulted ceiling, this rooftop perched upon Chicago Athletic Association Hotel is an excellent choice come rain or come shine. At Cindy’s, you’ll be able to enjoy your favorite comfort food while taking in the gorgeous panoramic views of Millenium Park and Lake Michigan. Their seasonal menu also features a rotating selection of “bio-dynamic wines and award-winning cocktails” such as their Old Fashioned ($16) and their  “Effective Immediately” ($10) for which the restaurant is currently donating $2.00 per drink sold to the My Block My Hood My City’s foundation in aid of Chicago’s Black communities.

You can find Cindy’s at 12 S Michigan Ave.

4. Etta, Wicker Park


Etta is an excellent choice if you’re looking for home-made Italian food. Their pasta team starts hand-rolling their dough at 5 am every morning for you to enjoy some delicious pasta dishes like their “Cavatelli Bolognese” ($16) that come served with a delicious parmesan fondue (🤤). For dessert, we suggest trying their “The Celebration” ($5/person), a slew of coffee shots served with birthday cake macaroons.

You can find Etta at 1840 W North Ave.

5. Federales, Wicker Park

As far as modern Mexican rooftop eateries go, Federales is one of our absolute favorites. At this open-air tequila and taco restaurant, you’ll be able to enjoy a delicious selection of slow-roasted meats with some excellent homemade margaritas ( one of our favorite ones is the Spicy Watermelon Margarita!).  And if you’re looking for a fun night, Federales’ got your back too! The Wicker Park rooftop turns into a full-on fiesta once the sun goes down.  While you’re at Federales, we also suggest trying your hand at shot throwing with their signature tequila bell. Get 8 tequila shots in ice glasses and test your aim by throwing it at Federales’ bell, you’ll be in for a super fun night you might forget–or not, it all depends on the shot count!

You can find Federales at 180 N Morgan St.

6. Floating Rooftop at Chicago’s First Lady, Riverwalk

Celebrate summer in style while sipping on local spirits at Chicago’s one and only floating rooftop bar! Chicago’s First Lady Floating Rooftop is located on the upper deck of one of Chicago’s First Lady luxurious vessels which is currently docked on the Riverwalk. Here you’ll be able to enjoy a bevy of refreshing summer cocktails, wine and other spirits while you take in the beautiful views of the Riverwalk this water-bound location has to offer. Our favorite drink? Their Chicago Mule ($11) with grapefruit and rose-infused vodka–a totally refreshing twist on the classic. The floating rooftop works on a first-in, first-served basis and requires no reservation so you can just walk up to the spot and cozy up on one of their tables for up to 90 minutes!

You can find Chicago’s First Lady Floating Rooftop dock on the Riverwalk between Michigan Avenue and Wacker Drive.

7. Homestead on the Roof, East Village

Enjoy some delicious farm-to-table dishes at this rooftop located in East Village. Homestead on the Roof features a seasonally-rotating menu that incorporates ingredients sourced directly from their on-site garden, a lovely patch of greenery you’ll get to enjoy and look at while dining at Homestead. This summer, the restaurant’s menu features home-made dishes based on their chefs’ cultural roots such as Chef Ivan’s “Mole Negro” a traditional dish from his home state of Michoacan, Mexico.

You can find Homestead on the Roof at 1924 W Chicago Ave.

8. Joy District, River North

If you’re looking for a laid back time or you’re looking for a fun night out,  Joy District’s the place to go! This summer, the multi-tiered club will be holding  rooftop yoga classes with bottomless mimosas  every weekend to help you start your morning right. But if you’re looking for a bit of (safe) partying,  you’ll find that Joy District’s rooftop offers quite the lively scene after 5pm.

You can find Joy District at 112 W Hubbard St. 


9. Prairie Terrace at the Ace, West Loop

Want to enjoy a relaxing evening of music and cocktails? Then we suggest heading over to the Prairie Terrace at the Ace Hotel. At the Prairie Terrace you’ll be able to lay back and enjoy the gorgeous Chicago views while listening to some wondrous classical numbers in an enchanting candlelit setting all while sipping on your favorite cocktail. It’ll be an evening you won’t forget!

You can find the Prairie Terrace at 311 N Morgan St.

10.  Streeterville Social, Streeterville

 Located on the third floor of the Loews Hotel, Streeterville Social is the perfect place in which to relax in swing chairs and chill out with friends while playing giant Jenga. This summer, the rooftop has partner with a number of local businesses to bring you some of the best food and drink in Streeterville; these include Pinched on the River, D4 Irish Pub & Café and Luella’s Southern Kitchen among others.

You can find Streeterville Social 455 N Park Dr.

11. The Promontory, Hyde Park

This stylish and modern eatery based in Hyde Park is perfect for a low-key evening of excellent food and live music. The Promontory offers delectable dishes cooked in their open-hearth kitchen along with some excellent traditional cocktails with a twist such as their Earl Berry Collins ($11) with strawberry vodka and Earl Grey tea that are an absolute must-try! If you’re a music fan you can also catch a live show while at the Promontory and celebrate the era when Chicago’s South Side was the capital of American music. Due to COVID-19 restrictions, The Promontory’s rooftop is currently opening only Friday through Sunday from 3 pm until 11 pm.

You can find The Promontory at 5311 S Lake Park Ave.

13. The Rooftop Bar at Nobu, West Loop

Say hello to the newest member of the Chicago bar scene! At  The Rooftop Bar at Nobu Hotel features you’ll be able to enjoy Nobu’s take on Japanese-Peruvian fusion cuisine in the shape of a wide range of small dishes such as nori tacos ($15/pc) with caviar and avocado, wagyu dumplings ($26) with smoked jalapeño miso that are perfect for sharing. Pair these with one of Nobu’s signature cocktails and you’ll be in for a lovely evening set against the backdrop of Nobu’s killer skyline views! The Rooftop Bar is open every day from 4 pm until 10 pm with nightly live performances. Reservations are required and spaces are limited so we recommend booking your spot ahead of time.

You can find The Rooftop Bar at Nobu at 155 N Peoria St.


14. VU Rooftop, Near South Side

Located 22 stories high next to McCormick Place VU offers some absolutely gorgeous views of the Lake and Downtown Chicago. On its 3,000-foot space, you’ll find three different bars and two patios in which to enjoy some top-notch cocktails and bites. VU follows a classy and fun dress code so make sure to pull out your best outfits for the occasion and leave your beach shoes and shorts at home.

You can find VU at 133 E Cermak Rd. 


13. Whiskey Business, Wicker Park

With more than 100 different whiskeys and over 20 beer choices on the menu, you know you’re bound to find your perfect summer drink at Whiskey Business. Their 3,000-foot rooftop is awesome for a relaxed and laid-back time with friends while sipping on some killer drinks, whether you choose to chill out at their “Rooftop Beach Club” during the day or vibe with their dazzling new laser show “Neon Reef Nights” during your weekend nights!

You can find Whiskey Business at 1367 N Milwaukee Ave.


See also: PB&J Restaurant Opens In West Loop, Offers A $350 Peanut Butter And Jelly Sandwich

[feature image: @marilyn_bergeron, Instagram]





Food & Drink