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West Loop, Near West Side, Pilsen Outdoor Drinks, Happy Hours and Entertainment!

Outdoor bars in Pilsen, Little Village, West Loop and the Near West Side are a great way to enjoy the warm weather. But who has the best happy hour? The best drinks? The best views? We're here to help you figure that out. This diverse area is home to a thriving Mexican-American community, trendy dining and nightlife spots and smaller, distinct neighborhoods that reflect a unique mix of city life, from the University of Illinois at Chicago to Greektown and the United Center.

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County Barbeque

A hefty list of craft beer, cocktails and spirits get served alongside the specialty here: slow-smoked barbecue with custom seasonings that reflect regional favorites. The cocktail list mimics the dine-in fare, with drinks named Mighty Smoked Pines and Cornbread Moon. Bright plaids adorn the outside walls and the outdoor patio is just as colorful.   
1352 W. Taylor St., Chicago, Illinois 60607
312-929-2528
312-929-2528
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RM Champagne Salon

Locals know this spot as a hidden gem, tucked into a cobblestone alleyway with a speakeasy vibe. The menu has French bistro classics and the drink list focuses on bubbly champagne. At every turn, you’ll be surrounded by elegant, eclectic décor, with candlelit rooms, antique mirrors and indie rock pumping through the speakers. 
116 N. Green St., Chicago, Illinois 60607
312-243-1199
312-243-1199
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Three Aces

Happy hours at Three Aces often spotlight a Chicago beer paired with burger or pizza specials. There’s a beer garden, too, but the bar takes happy hour to another level by offering Hangover Happy Hour on Sunday mornings with $3 Bloody Marys. Listen to live music during special events or Three Aces’ monthly concerts.  
1321 W. Taylor St., Chicago, Illinois 60607
312-243-1577
312-243-1577
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Wise Owl Drinkery & Cookhouse

Find unique American fare and craft cocktails at this brew bistro, where you’re encouraged to bring pals and pets to the patio. Chill in the bags court, devour an $8 daily lunch special or scope the weekend’s live entertainers. Never-ending specials include $3 craft cans, $5 Martini Mondays and sangria or mimosa on weekends.
324 S. Racine Ave., Chicago, Illinois 60607
312-374-8915
312-374-8915
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Little Goat Diner

Part of Stephanie Izard’s Chicago empire, Little Goat looks over downtown from its West Loop rooftop bar. There’s a bakery and gourmet comfort food restaurant inside; order there and have lunch or spend the night up top with beer and cocktails. But call ahead — private dining reservations will help you secure an open rooftop. 
820 W. Randolph St., Chicago, Illinois 60607
312-888-3455
312-888-3455
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Dusek’s

Housed in a historic 1892 building, Dusek’s mixes kitschy knick-knacks with southern and Asian fusion cuisine, obscure craft beers and regular events. The Tack Room, a cocktail bar in the property’s old carriage house, has a patio that overlooks Pilsen and there’s a lively piano show every night. Grab a Rob Roy cocktail and embrace the atmosphere. 
1227 W. 18th St., Chicago, Illinois 60608
312-526-3851
312-526-3851
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