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South Chicago, East Side, Pullman & Roseland Outdoor Drinks, Happy Hours and Entertainment!

Outdoor bars in South Chicago, the East Side, Pullman and Roseland 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. Home to a surprising selection of restaurants, the South and East sides have drink deals that rival anything you’ll find to the north and some of the city’s most famous eateries. You’ll be glad you ventured beyond the Loop. In Pullman and Roseland, you’ll find stone-sided bungalows, Tudor-style homes peppered with wrought-iron accents, neighborhood pubs and several breweries that reflect this area’s railcar factory foundation and old-school Chicago.

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Calumet Fisheries

No seating, no bathrooms, no problems for fans of Calumet Fisheries, where the smokehouse is worth the drawback of takeout only. Summertime crowds gather — some savoring catfish or shrimp on the street, others in their cars. The 65-year-old, family-owned pit stop delivers a one-of-a-kind South Side experience. Fish is marinated in brine overnight, then smoked over oak logs. 
3259 E. 95th St., Chicago, Illinois 60617
773-933-9855
773-933-9855
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Skyway Dog House

It doesn’t get more Chicago than a summertime visit to the 40-year-old Skyway Dog House. You can’t miss the bright yellow and red signage on its brick exterior, nor the neon sign declaring “Hot Dogs” Go to the counter, treat yourself to a Vienna Beef and snag a picnic table outside. You won’t regret it.
9480 S. Ewing Ave., Chicago, Illinois 60617
773-731-2000
773-731-2000
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Judi’s Sports Bar

Locals rave about this newly remodeled neighborhood hangout, especially its  cheap (and delicious) cocktails, friendly bartenders and fried chicken. Judi’s Long Island iced teas are a favorite. Come by the bar, grab a drink and listen to the DJ spin a mix of new and old-school hits. 
512 E. 103rd St., Chicago, Illinois 60628
773-660-1733
773-660-1733
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Leon’s Barbecue Zone

This standalone spot is one of two Leon’s Barbecue Zone locations in the city. It doesn’t have outdoor seating, but as the larger of the duo, its indoor space is expansive enough to comfortably accommodate large parties. Visit for fan favorites like rib tips and hot links — two menu items featured on "Chicago’s Best". 
3309 E. 106th St., Chicago, Illinois 60617
773-374-9663
773-374-9663
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Route 66

Get your pizza fix at Route 66 or try its chicken wings for a taste of the cooks’ renowned hot sauce. This summertime hotspot features modest outdoor seating where diners can dig into a doughy hand-tossed or thin-crust pie. If you feel adventurous, try Route 66’s signature jalapeño pizza.
10180 S. Indianapolis Ave., Chicago, Illinois 60617
773-734-2032
773-734-2032
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Excalibur Club

As one of the few hangouts on its stretch in Pullman, The Excalibur Club — not to be confused with River North’s now-shuttered nightclub — beckons the area’s late-night crowd via a neon cocktail sign and orange awnings. Last call sends patrons hoofing at 1 a.m. on Sundays; 2 a.m. on weekdays; and 3 a.m. on Saturdays. 
451 E. 111th St., Chicago, Illinois 60628
773-995-9187
773-995-9187
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Argus Brewery

Explore the rich history of a South Side 1900s horse stable-turned-brewery while savoring world-class beers straight from the barrel. Argus Brewery’s 90-minute Saturday tours are ticket-only affairs available on a first-come, first-served basis. After your tour, hang out in the bar area and listen to live music, or enjoy bocce ball on a soon-to-be-built court adjacent to the brewery. 
11314 S. Front Ave., Chicago, Illinois 60628
773-941-4050
773-941-4050
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El Charro San Francisco

Searching for authentic Mexican eats? The colorfully decorated El Charro San Francisco might be as good as it gets this side of the border. Choose from daily specials like made-to-order flautas de pollo and chiles rellenos, or score a 20-taco tray for $35. El Charro caters to late nighters and stays open until 1:30 a.m. most days.  
3655 E. 106th St., Chicago, Illinois 60617
773-734-3584
773-734-3584
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