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5 Cocktail Spots to Kick Off Summer in the Chicago Loop

Posted  5 years ago  in  Eat & Drink

3 MIN READ - Summer, the most beautiful season in Chicago, is here, which means you’ll want to treat yourself to an ice-cool cocktail to stave off the sweat. Ditch the indoor bars for a change and transport yourself to a shaded veranda overlooking the lake, or a rooftop patio as the sun sets at these urban escapes in the Loop.

Land & Lake Kitchen

Start patio season on the right foot with some delicious cocktails at Land & Lake Kitchen. The Midwest influenced bar program includes a selection of cocktails made using locally distilled liquor. Highlights include the Green & Grass with Almighty Spirits Vodka, cucumber, lemongrass, lime, and soda and The Pink Lady with gin, raspberry, lavender, mint, lime juice, and tonic water. Learn More

Grant Park Bistro

Add a French twist to your summer at Grant Park Bistro. The cocktails at this new French bistro on Michigan Avenue are all influenced by different regions in France. Highlights include the Le Cassis with Magdalena rum, elderflower liqueur, passionfruit, and lime, and the Mont Ventoux with Tanqueray gin, thyme, and fresh lime. All cocktails are paired with Grant Park’s menu of delicious French dishes. Learn More

Grant Park Bistro Photo Courtesy of MADN Agency

Island Party Hut

The tropical drinks of Island Party Hut bring a taste of the islands to Lake Michigan and the Chicago Riverwalk. Its classic cocktail drinks feature The Riverwalk Rambler, The Lime in D’ Coconut, The Hammock, Mai Tai, Dark & Stormy, Margarita, Painkiller, and Wiki Wiki Root Beer Float. With bocce ball, bag games, Jenga, Bimini Island Ring game, and live music on weekends, Island Party Hut is one of the most popular summer destinations in Chicago. Learn More

Cindy’s Rooftop

Only at Cindy’s will you find award-winning cocktails with panoramic views of Millennium Park, Lake Michigan, and beyond. Carefully crafted cocktails like Jillian, No Bars, Farmer’s Gin and Tonic, Fab Five, Piña Colada, Sundown, and Oaxacan Highball are perfect for al fresco libation. Created out of thin air, the aery atmosphere gives contrast to the Association’s history as a men’s club, yet carries an unmistakable look of having always been here. Learn More


Behind the bar, you'll find Southern Hemisphere standbys like Fernet & Cola, Chicano’s, and the seasonal Pisco creations crafted by head bartender Sam Garcia and team. If you’re going with a group, be sure to grab the large format lunch bowl. Named after a move from Argentine tango, Boleo brings dramatic flavors and sultry beats of South America to a swanky rooftop on the 15th floor of the Kimpton Gray Hotel. Up here, the crated playlist never ends, and the savory aroma of Peruvian and Argentinian street food perfumes the air, while a massive retractable glass roof keeps the vibe warm regardless of the season. Learn More

Eat and Drink

Explore more exquisite drinks and dynamic night life in the Chicago Loop.

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If you’re going to drive to the Loop, download the iParkit mobile app for discounted parking at any of InterPark's 18 city-wide locations. It will give you easy access to the city's best attractions. Millennium Garages also offers multiple convenient parking garages, and you can secure your spot ahead of time online. If you are going to be drinking, we recommend you take a Lyft or the CTA for a safe ride back home. Click here to plot your route.

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