Chicago Rooftop Season

Chicago Rooftop Season By Marissa Rainone

Summer is here, which means Chicago Rooftop Season is here! Chicago has so many rooftops to pick from, it’s hard to choose just one. Don’t worry, we’ve got you covered. Check out our list of some of the best rooftops Chicago has to offer.

Cindy’s Rooftop

Looking to find breathtaking panoramic views of both the city skyline and Lake Michigan? Look no further than the popular Cindy’s. Set on the rooftop of the Chicago Athletic Association hotel, overlooking Millennium Park, Cindy’s features both a spacious indoor lounge with floor-to-ceiling windows and an open-air rooftop terrace. Enjoy the locally-sourced, New American menu within the relaxed atmosphere of a Great Lakes beach house, while you enjoy the view of Chicago’s own Great Lake.

Rosebud on Randolph

This brand new flagship Rosebud location is the perfect spot for a tasty weekend brunch, lunch, or dinner. Or head to the penthouse level Cocktail Club for a libation of your choosing. Needless to say your drink comes with spectacular views of the world famous Millennium Park. Z Bar

High above bustling Michigan Avenue on the sixth floor of The Peninsula Chicago you will find the upscale, internationally inspired Z Bar. Enjoy specialty cocktails and tasty bites while admiring the incredible views around you. Z Bar also offers the monthly “Wanderlust Cocktail Class” showing you how to create your own favorite cocktail.

Flash back to better days with the 80s-and-90s-inspired rooftop bar, Whiskey Business. At this vibrant and quirky rooftop you can enjoy your favorite classic movies on their 100-inch TVs and the sounds of 80s and 90s music all night long. Choose from over 100 different whiskeys, specialty cocktails, and a wide range of delicious foods.

London House Rooftop

This tri-level rooftop bar above the London House Hotel is widely considered one of the best in the city and it’s easy to see why! With stunning views of surrounding buildings and the Chicago River AND Lake Michigan, delicious cocktails, tasty bites and a vibrant atmosphere, the London House is perfect for a special night out!

Utopian Tailgate

Looking for something fun for your group of friends? Check out Chicago’s favorite adult playground, Utopian Tailgate. Located above the Second City Comedy Club, this 10,000-square-foot rooftop bar includes tire swings, yard games, colorful picnic tables, and eye-catching views. Feed your inner child with elevated bar food while sipping decidedly un-childlike cocktails and draft beers.

Homestead on the Roof

Take a trip to the rustic countryside with Homestead on the Roof located above Roots Handmade Pizza in West Town. This literal farm-to-table rooftop trades Chicago skyline views for over 3,000-square-feet of organic rooftop gardens. With elegant cuisine and amazing cocktails, this small rooftop serves as the perfect intimate setting for a romantic night out.

Offshore Rooftop & Bar

Check out the nation’s largest rooftop venue, Offshore Rooftop & Bar, featuring a 36,000-square-foot indoor lounge and a 20,000-square-foot outdoor terrace. Sited on the third floor of Navy Pier’s Festival Hall, the panoramic views of the lake and skyline are like nowhere else. To make your experience even better, Offshore offers delicious small plates, fresh American cuisine, and select cocktails. Open year-round in all weather.