Exploring South of Chicago's Loop | Midwest Living
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Exploring South of Chicago's Loop

Two different neighborhoods stand ready to wow you south of Chicago's Loop.
Chicago's Pilsen neighborhood. Photo courtesy of Choose Chicago.
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Prairie Avenue Historic District. Photo courtesy of Choose Chicago.
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Chicago’s South Loop and Pilsen neighborhoods stand next to each other, but they couldn’t feel more different. Our top 10 list of favorite stops balances South Loop buildings from the Gilded Age with modern flavors of Mexico in Pilsen. A bonus? You can drive—and park—with ease (just stick to our faves; side streets can look a bit dicey).

1 Prairie Avenue Historic District Mansions create an architectural timeline representing Chicago’s 19th-century rise from rugged frontier town to cosmopolitan city. Interpretive panels stretching along the 1800 block of South Prairie Avenue explain the history behind where Chicago’s elite families (Field, Armour and Pullman) lived. (312) 567-8500; choosechicago.com

2 Clarke House Museum Docent-led tours of the city’s only surviving Greek Revival-style home (built in 1836) highlight decorating tastes and life in mid-19th-century Chicago. (312) 745-0040; clarkehousemuseum.org

3 Glessner House Museum The 1886 Richardsonian Romanesque mansion introduces modern architectural concepts and Arts and Crafts decorative features that influenced Frank Lloyd Wright. (312) 326-1480; glessnerhouse.org

4 Gioco Beef, veal, plus homemade pastas that do Italy proud, shine in the casual 1890s brick space, a former speakeasy sporting 1920s gangster graffiti and a walk-in safe Al Capone reportedly used. (312) 939-3870; gioco-chicago.com

5 South Michigan Avenue Giant sidewalk plaques provide a self-guided tour of cultural sites shaping Chicago’s identity. Tiffany glass windows and Arts and Crafts murals adorn Second Presbyterian Church. Called Motor Row in the 1920s, the avenue has terra-cotta-clad buildings used as auto showrooms until the 1960s, when blues recording studios moved in. Chuck Berry, Muddy Waters and the Rolling Stones cut hits at Chess Records. (312) 567-8500; choosechicago.com

6 Acadia Global flavors arrive artfully plated (though puny-portioned) at this special-occasion restaurant. During our visit, the slaw—made with smoked banana, apple and celery root—on pork belly successfully blended unusual flavors; expect other surprises from the ever-changing menu. Prix fixe menus begin at $65 for three courses. (312) 360-9500; acadiachicago.com

7 Pilsen Kaleidoscope-color murals splash across storefronts, alleyways and train viaducts; historic churches anchor corners; and ranchero music spills from taqueria stands. Concentrated on West 18th Street between Ashland and Blue Island avenues, Pilsen hums, thanks to The Sabina Tortilla Factory (selling warm corn tortilla chips), religious art stores, funky vintage resale shops (Pilsen Vintage and Thrift) and Mexican folk art shop Artesanias D’Mexico. East Pilsen’s vibrant Chicago Arts District has 30 gallery-studios clustered around 18th and South Halsted streets; to explore them all at one time, plan to attend free art walks held the second Friday of each month. (312) 567-8500; choosechicago.com

8 National Museum of Mexican Art The nation’s largest accredited Latino art museum displays diverse pieces and Mexican artwork. The free-admission museum’s annual Day of the Dead exhibit and folk art festival celebrate life and death, September 13–December 15, 2013. (312) 738-1503; nationalmuseumofmexicanart.org

9 Nuevo Leon Line up with locals for heaping platters of homemade Mexican faves. Order the daily special (you’ll find it listed on the corn-yellow stucco wall), or simply stick with great-tasting tacos or fajitas. Prices run from $6 to $14, and you can only pay in cash. (312) 421-1517

10 Wheeler Mansion An elegant, restored 1870 mansion thrives as a relaxing 11-room boutique inn ideally located a block from Lake Michigan and the Prairie Avenue Historic District. From $296, includes breakfast, Wi-Fi and parking. (312) 945-2020; wheelermansion.com

For more information: Choose Chicago (312) 567-8500; choosechicago.com

(A version of this story appeared in Midwest Living® September/October 2013.  Prices, dates, and other details are subject to change, so please check specifics before making travel plans.)

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