The scene at iconic Wicker Park music venue Subterranean
Bucktown/Wicker Park blew up in the ’90s with a buzzing art scene and some of the city’s hottest restaurants, all centered around the six-way intersection of North, Damen and Milwaukee avenues. The area’s grit has evolved into a scruffy glamour, and it’s still one of the city’s most exciting districts. Here are our favorite places to eat, drink, hang out and absorb Bucktown/Wicker Park’s still-rich culture.
Where To Eat
1531 N. Damen Ave. / Website
Expect excellent craft beers, creative cocktails, fab fare and a hip crowd at this scenester-laden taqueria.
1824 W. Wabansia Ave. / Website
An inviting old-school vibe, reliable Italian fare and killer martinis have made this a Bucktown staple since 1990.
1742 W. Division St. / Website
One of the city’s finest tasting menus can be found at this hidden gem behind South Asian bar and resto Lilac Tiger (formerly Wazwan); chef/owner Zubair Mohajir crafts multiple Indian-inspired tasting menus plus wine/cocktail pairings.
1415 N. Wood St. / Website
New Orleans-inspired fare and authentic Southern hospitality are at the heart of this lively spot, whose menu features everything from boudin balls and deviled eggs to grilled oysters, po’boys and more.
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1958 N. Damen Ave. / Website
You’ll savor the beauty of this dining room as much as you do the classic French bistro fare, which is some of the city’s best. Frosted glass sconces, a mural of Paris and a high-energy crowd mingle elegance with conviviality.
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1466 N. Ashland Ave. / Website
Prepare for a one-of-a-kind tasting menu experience at this intimate BYOB hideaway from notable chef and owner Michael Carlson and team.
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1804 W. Division St. / Website
From baby back ribs and rotisserie chicken to cole slaw, cornbread, mac and cheese and collard greens, this neighborhood institution serves up some of the city’s best ‘cue.
See Also: The Ultimate West Loop Neighborhood Guide
Where To Shop
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1935 W. North Ave. / Website
Dramatic, moody floral arrangements, stunning fine jewelry and intriguing gifts and accessories are the hallmarks of this eclectic boutique, a neighborhood fave since 1999.
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1342 N. Milwaukee Ave. / Website
From Japanese denim to premium boots, outerwear, accessories and more, this men’s and women’s wear boutique focuses on top-quality merchandise that is made to last.
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1564 N. Milwaukee Ave. / Website
One of Chicago’s best sources for new and used books, this Wicker Park institution boasts an inventory of over 60,000 volumes and hosts frequent readings, author events and more.
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1913 W. Division St. / Website
Smart fashion, accessories and home goods for men, women and kids have made this indie boutique a draw since its opening in 2002.
1529 N. Milwaukee Ave. / Website
A curated mix of selects from brands like Nike, Stussy, Patta and Adidas make this a must-stop shop for streetwear and footwear aficionados across the city.
1438 N. Milwaukee Ave. / Website
One of the world’s most in-demand streetwear brands of the moment has set up shop in the heart of Wicker Park’s boutique strip. In the 1,800-square-foot space, the art is just as curated as the hats, shirts, jackets and skate decks that line the racks, highlighted by skater/artist Mark Gonzales’ massive “Schminx” sculpture, finished in metallic gold with a handpainted face.
See Also: The Ultimate Lakeview Neighborhood Guide
Where To Stay
2018 W. North Ave. / Website
Towering above Wicker Park and Bucktown, this 1929 art deco gem has been transformed into the hippest hotel on the city’s northwest side, drawing guests and locals alike with ’90s-inspired hang Clever Coyote and popular rooftop bar The Up Room.
See Also: The Ultimate Chicago Neighborhood Guide
Hit The Town
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1543 W. Division St. / Website
Set in a historic, terra cotta-clad 1918 building, this beloved neighborhood venue hosts some of the city’s most diverse programming, from musical theater and live concerts to Polish and Eastern European cultural events inspired by the area’s immigrant history.
1383 N. Milwaukee Ave. / Website
Chicago’s cabaret scene is alive and well at this intimate venue, which hosts crooners, comics and local piano bar legends in two performance spaces a few nights a week.
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1331 N. Milwaukee Ave. / Website
Stand-up comedy, theater, podcast tapings, fashion shows—any or all could be on the docket at this lively venue, a fave local destination since 2010.
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1949 N. Hoyne Ave. / Website
A mecca for beer lovers, this “traveler’s tavern” is decked out with wanderlust-inspiring maps, globes, travel books and more, adding warmth and an inviting vibe to the attraction of its 200-strong global beer list.
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2011 W. North Ave. / Website
One of the city’s most iconic live music venues, this historic 1890s building has hosted acts ranging from Fall Out Boy and Alabama Shakes to Lee Scratch Perry and Dinosaur Jr.
1520 N. Damen Ave. / Website
The O.G. Chicago mixology bar, this hushed, curtained salon of libations has drawn crowds—who are happy to wait outside the unmarked entrance for a coveted seat to open up, as standing room is most definitely not allowed—for its expertly handcrafted cocktails since 2007.
Where To Relax
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Entrance at 1801 N. Milwaukee Ave. / Website
Located on a former abandoned elevated railway, this 2.7-mile trail has been transformed into a beloved green space for everyone from joggers and cyclists to families with kids.
1743 W. Division St. / Website
From massages and facials to intuitive readings and energy healing, this Division Street destination has been a wellness go-to since 2002.
Photography by: Big Star photo courtesy of Cassie Stadnicki; Coach House at Wazwan photo courtesy of Shon Gibbs Imagery; Robey photo by Adrian Gaut; Violet Hour photo by Kelly Sandos; other photos courtesy of brands
