Sipping at Chicago’s Best Rooftops

All it takes is 3 warm months a year to remind us why we love the city of Chicago. After the harsh winter we have experienced this year, it’s no surprise that Chicagoans are maximizing their time outdoors, whether it’s dining al fresco or sipping a refreshing cocktail at one of the many rooftop bars in the city. Here we cover three bars with distinct styles that can satisfy every reader.


Located on the 18th floor of the luxurious Rafaello hotel is the swanky Drumbar – a refined bar for the cocktail enthusiasts. The hotel’s bold character seeps into the speakeasy style bar that boasts three sections: A dim lit interior with deep leather sofas, bright brass, antiques and black and white photos on the wall; a chic rooftop with fire pits and fantastic views of Lake Michigan and the Hancock building; and a narrow corridor with marbled arches and small tables for those looking for some privacy.


Rooftop Drumbar

The man behind the outstanding bar is the charming and talented Alex Renshaw. Having left his corporate career he moved to Chicago to try his hand out for improv and along the way found his true passion in mixology. 


Alex Renshaw – Head bartender

Drumbar’s theme is classic and chic, it’s not molecular, it’s not clubby. Currently there are lots of light refreshing flavors – stuff you can drink in the patio. – Alex Renshaw

The cocktail menu boasts several classics along with seasonally inspired concoctions created by Alex Renshaw & his team.  The Business Lunch, a Paul Bastien creation, is a refreshing cocktail version of a classic summer salad made with Linie Aquavit, strawberry, arugula and white wine vinegar. Another cocktail to look out for is Alex Renshaw’s creation Beg Your Pardon – jalapeno infused chartreuse with a hint of pineapple and lemon that has a nice spicy kick to it.


Mojito at Drumbar

"Business Lunch" at Drumbar

Business Lunch at Drumbar



The J.Parker rooftop, perched atop the sleek Hotel Lincoln, offers some of the most stunning views in the city, looking out over Lake Michigan, Lincoln Park Zoo and the Gold Coast. There’s just something about this part of town that makes it so dreamy, from the captivating neighborhood to the chic people that frequent the area making the J.Parker a great place to people watch. 

J.Parker – Eric Kleinberg Photography

Part of the Boka Restaurant Group, the J.Parker offers small-plates by award-winning Chef Paul Virant (The Perennial Virant) and destination cocktails by beverage director Adam Halyckyj that pay homage to a different part of the world each time. The contemporary décor with the snug couches and high top tables makes this rooftop an ideal spot for a relaxed drink this summer. 


Spring Drinks at J.Parker – Eric Kleinberg Photography


IO Urban Roofscape

True to its name, this new and trendy hot spot in the River North area is an indoor and outdoor rooftop bar with a retractable ceiling and sleek décor. Away from the lake view this rooftop still offers splendid city skyline views from its 4th floor. It’s casual ambiance during the day transforms to a high-energy nightspot after 6pm. The trendy crowd and loud music reminds one of the night scene in LA or Vegas.


IO Urban Roofscape

Chef Riley Huddleston, formerly of The Aviary, brings in his culinary experience and talent to the Godfrey offering an extensive food as well as drinks menu. The menu features Chicago favorites such as the Pastrami Sandwich as well as popular signature cocktails such as margaritas that are prepared using scientific measurements to ensure consistency- an approach that may have been inspired by his time in the Aviary.

IO Margarita Cocktail

Margarita cocktail at IO Urban Roofscape

IO Urban Roofscape:





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