Let’s start this walking tour of some of Chicago’s most vibrant and diverse communities at the historic heart of Logan Square, the Illinois Centennial Monument. Designed by the architect of the Lincoln Memorial in Washington, D.C., this 70-foot marble column and surrounding park has served as a neighborhood gathering space, concert venue and protest backdrop since 1918, commemorating the state’s 100th anniversary.
Across from the monument, Lula Cafe has become an absolute fixture of Logan Square since opening its doors in 1999. This artfully renovated storefront offers a delicious, locally sourced brunch menu, and farm-to-table dinners in the evening—all at prices accessible to the whole community. If there’s a bit of a wait for a seat on the patio, head to Boulevard Bikes next door, or grab a great cup of coffee or chai at New Wave Coffee, just across Milwaukee Avenue.
If you’re ready to walk-off your breakfast burrito, stroll south toward Palmer Square Park, a seven-acre grassy greenspace nestled in Logan Square. Conceived as part of the city’s boulevard system in the 1870’s, the park hosted popular track bike races over a century ago, and walking the tree-lined paths of the park today, you’re still likely to see more than a few fixed-gear bicycles—as well as slackliners, young families out for picnics, and some serious frisbee matches. From the east side of the park, head south through the wide gardens of Humboldt Boulevard to take the ramp up to the elevated 606 multi-use trail, opened in 2015.
Take in a unique view of the residential neighborhoods between Logan Square and Wicker Park from this converted railway, and exit the trail at Churchill Field, just east of Damen Avenue. Walking south on Damen, you’ll soon reach Chicago’s bustling “six corners” intersection of Milwaukee, Damen and North. The Flat Iron Arts Building and the Northwest Tower across the street are the early 20th-century architectural pillars of this neighborhood, with artists, musicians and theater groups still hosting open-studio events regularly in the Flat Iron.
Across Milwaukee Avenue, stop into Myopic Bookstore, an eclectic (but organized!) maze of used books housed in a three-level storefront, with a cozy “living room” reading area upstairs. Milwaukee Avenue plays host to some truly thriving independent businesses; budget some time for browsing art, furniture, and clothes, and don’t forget to stop into Reckless Records, an institution in the Chicago music community.
Head south on Wood Street, and after a block or so, you’ll wonder if you’re still in the same city. In the shade of tall old trees, you’ll stroll past red brick Wicker Park homes, crossing into West Town.
This area is quickly developing a reputation as one of the best restaurant hubs in the Midwest, anchored by Chicago Avenue storefronts. Whether you’re grabbing a taco at Flo, enjoying a brew and some Quad Cities style pizza at Roots, or sampling sushi and robata (think: Japanese barbecue) at Yuzu, make sure eating is a priority in this neighborhood! Stop into West Town Bakery for a dessert and coffee, or walk down the block to Comrade Bicycles, a local shop that stocks unique commuter bikes and retro steel-frame racers.
The real beauty of ending this day in West Town is the neighborhood’s more or less central location in the city. If you’re staying downtown, you can grab the Chicago bus back toward your hotel, catch the Blue Line train toward O’Hare at Division, or maybe just grab a cab back to your Airbnb. Kick back and relax, it’s been a full day on foot in the city!
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This great little BYOB sushi & robata grill in West Town calls itself "Japanese Inspired", taking some delicious creative liberties with traditional cuisine.
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With sustainably-sourced ingredients and lots of vegan and gluten-free options, this cozy bakery and diner does its best to be accessible to everyone in the community. Cakeballs from West Town are a...
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Walking into New Wave Coffee makes me feel like I never left college, in all of the right ways. The checkered floor and lived-in vibe of this popular Logan Square coffeehouse makes for a great meet-up...
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Lula Cafe opened its doors in Logan Square in 1999, and has since become the brunch and farm-to-table hub of the Logan Square. The patio is highly recommended, and worth the wait in the summer!
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Scratch that vinyl-collecting itch at Reckless Records' new flagship location in Wicker Park, with an overwhelming collection of records, CD's and tapes, not to mention in-store performances.
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This staple of Wicker Park houses galleries, theater spaces, and artists' lofts, with regular shows and open houses.
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