Single Girl Summer’s Guide to Chicago’s Hottest Rooftops

Single Girl Summer’s Guide to Chicago’s Hottest Rooftops

Summertime Chi…There’s nothing like it…so hot, so much to do, but so little time. Make every moment count by enjoying your dinner or drinks on a fabulous rooftop. Here’s a Sweet Sixteen list (in alphabetical order) that’s Single Girl Summer approved:

1) Citizen (River North at 364 W. Erie Street) With tasty food and fun crowd, this is the place to be for an after work cocktail. Stay from sun down until the moon comes up.

2) Epic Sky (Downtown at 112 W. Hubbard) This favorite spot is super-sexy-chic and the food is delicious. Get there early!

3) Fountainhead (Ravenswood at 1970 W. Montrose Avenue) You’ll forget you’re in the city lounging in this secluded “Old World” rooftop that specializes in craft beer, bourbon, scotch, and whisky.

4) Market (West Loop at 1113 W. Randolph Street) Recently voted one of the top 10 rooftops in the world, highlights at this gorgeous, posh spot include sleek wood furniture, a runway stage, huge flat screen TV, cooling fans that delightfully mist water from the roof (my favorite feature), and DJ’s on the weekends. The Director of Marketing at Market, Lauren Zeien, was kind enough to let me stage a photo shoot there. She even played the part of photographer. And as you can see from the picture below, Market has a wonderful view of the beloved Sears Tower (AKA Willis Tower).

5) NoMi Garden at the Park Hyatt (Downtown at 800 N. Michigan) Elegant and classy, this gem has the best view of Michigan Avenue and amazing food.

6) Plymouth (South Loop at 327 S. Plymouth Court) Unwind after a hectic workday at this causal getaway. Great happy hour specials and heaters so it’s open year round.

7) Reggie’s (South Loop at 2105 S. State Street) For the regular folks who love live music, deliciously cheap eats, wallet-friendly drink specials, and a cool-azz rooftop that has a free pool table, basketball hoop, corn hole, and lots of TVs to watch the games.

8) ROOF on The Wit (Downtown at 201 N. State Street) A Chicago favorite, ROOF has a breathe-taking view of the city, built-in fire pits and is a great place to rub elbows with celebrities, socialites, and social climbers.

9) Southern (Bucktown at 1840 W. North Avenue) Enjoy canopied cabanas, an ultra-cool South Beach vibe, and yummy Southern cooking including Johnny cakes and grilled shrimp and grits.

10) SushiSamba Rio (River North at 504 N. Wells Street) Enjoy your sake and sushi while being transported to a gorgeous Japanese garden.

11) The Terrace at the Conrad (Downtown at 521 N. Rush Street) Mag Mile Magnificence! Great atmosphere, appetizers and mojitos. Check out the Sunday movies at dusk.

12) The Terrace at Trump (Downtown at 401 N. Wabash Avenue) The drinks are pricey, but more than worth it for the amazing view at this 16th-floor oasis.

13) Twisted Spoke (West Town at 501 N. Ogden Avenue) The perfect pick for your next weekend brunch. This spot offers a diverse crowd, Bloody Mary menu, and unique motorcycle decor.

14) Vertigo Sky Lounge at the Dana Hotel (River North at 2 W. Erie Street) This upscale lounge has a great indoor and outdoor space, wrap-around glass windows, exotic Asian dishes, fire pits, and a strict dress code.

15) Wrigley Field Rooftop Club (Lake View at 3617 N. Sheffield Avenue) Located on the right field line at Wrigley Field, they specialize in corporate and group outings. With your package, your guests enjoy unlimited food and drinks while rooting for the Cubbies.

16) Zed 451 (Downtown at 739 N. Clark Street) Ascend an ultra-sleek staircase to this Zen garden reminiscent of a posh LA hot spot. If you're in the downtown area, call the restaurant and request the free Zed shuttle that will bring you right to the front door!

Deanna Burrell is the author of the dynamic novel “Single Girl Summer.” Described as the healthy, bouncing baby that would be produced if “Waiting to Exhale” and “Sex and the City” procreated, Single Girl Summer is available in paperback and ebook download. Visit for more information. Your summer won't be complete without it!

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