From soaring urban rooftops to cozy backyard patios, here’s a handful of concierges’ favorite places for summer bar crawls.
Do Downtown
Laura Trylong, a corporate concierge with AXA Assistance USA, recommends spending an afternoon and evening imbibing downtown. She suggests starting with a glass of Champagne at Raised, the Renaissance Chicago’s new third floor indoor-outdoor rooftop lounge before heading down to the Chicago Riverwalk and enjoying a frosty libation at waterside venues like Island Party Hut and City Winery. Afterward, she would cross the bridge at Clark Street and head down to river level to catch a baseball game and local brew on one of the big screens at Bridge House Tavern’s riverside patio before rounding out the evening with a nightcap on Smith & Wollensky’s flower-lined deck.

Raised
Lincoln Square
You know what pairs well with rooftops? Specialty meats. Gene’s Sausage Shop & Delicatessen, whose fantastic rooftop beer garden is essentially summer on a roof, is an ideal spot to relax and soak up some sun while enjoying a few sausages and pints. The view overlooks the main drag and an adorable block of shops, so it is a prime location for people watching as well.
Just a bit south of Gene’s you’ll find Fountainhead and one of the best neighborhood rooftops around. Although it can get crowded, rooftop seating here never feels cramped. Fountainhead has a stellar craft beer and whiskey selection, both of which are perfect for sipping the afternoon away.
Logan Square
Chicagoans and visitors alike can’t get enough of Parson’s Chicken & Fish, whose sprawling patio is best compared to a backyard BBQ. Laid back and casual, grab a spot at one of the communal picnic tables and do yourself a favor by ordering one of their negroni slushies. Paired with some buttermilk fried chicken and crunchy cool sides? You’ve got a can’t-beat summer experience.
Just down Armitage Avenue from Parson’s you’ll find Best Intentions, a neo-dive bar with an unexpected tropical hideout of a back patio. Here you’ll find a cabana bar, decorated with family heirlooms, offering select bottled and canned beer, wine, and an elevated cocktail program.

Parson’s Chicken & Fish. Photograph by Clayton Hauck.
Rooftop Hop
Concierges’ can’t get enough of Chicago’s rooftop lounges—and for good reason. With numerous options now dotting the landscape, they recommend soaking in those Instagram-worthy views at such hot spots as LondonHouse Chicago’s new and only tri-level rooftop venue LH; the Terrace at Trump, nestled in the shadows of iconic edifices like the Wrigley Building and Louis Sullivan’s Jewelers Building; and The J. Parker, offering incredible views of Lincoln Park Zoo and the famous curve of Lake Shore Drive.