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Photograph: Jessica Lynn Capron

Chicago's best shopping strolls

Shop till you drop while getting your daily dose of sunshine on these unsung retail-packed treks

Morgan Olsen
Written by
Morgan Olsen

When you've exhausted all of your usual window-shopping haunts, find something new on these underrated neighborhood strolls. We curated four walkable adventures that are packed with distinctive shops, from vintage furniture and rare books to limited-edition sneakers. Follow these trails to outdoor retail bliss.

Summer shopping adventures

For the decorator

West 18th Street in Pilsen | S Ashland Ave to S Halsted St

When it comes to vintage treasures and quirky home decor, there’s no better scene than Pilsen. The first stop on this trek is Knee Deep Vintage, where those who are willing to dig are rewarded with carefully curated retro clothing. Just down the street, you can spiff up your home library with literary gems from Pilsen Community Books. Green-thumbed shoppers should continue west to Verdant Matter, where succulents and handcrafted ceramics mingle in Instagram-worthy perfection. And when it’s time to head home, grab a sweet treat for the road from Panaderia Del Refugio (1339 W 18th St; 312-738-0128)

 For the unexpected finds
Photograph: Courtesy Tribeca

For the unexpected finds

West Madison Street in West Loop | S Racine Ave to S Halsted St

West Loop is known for its endless selection of top restaurants, but the 'hood is also home to some one-of-a-kind shops if you know where to look. For paper chasers, the Fig Tree and Smitten Boutique offer unparalleled selections of beautiful greeting cards and paper products. Just down the street, Leaders 1354 stocks pristine streetwear and shoes that sneakerheads will drool over. Pro tip: You’d be foolish to leave without stopping for a scoop of Jameson ice cream at Cone Gourmet Ice Cream.


For the last-minute shopper

North California Avenue in Humboldt Park | W Augusta Blvd to W Division St

If you’re on the hunt for a unique gift, head straight to Humboldt Park for an especially enjoyable stroll on a hot day. Your journey begins at Space Oddities Chicago, where taxidermy, altar candles, prints and books lie under one roof. Due north, the friendly folks at Humboldt House await in a colorful explosion of furniture, rugs, jewelry and giftworthy goodies. Give yourself ample time there before heading to Adams & Son Gardens, a.k.a. plant heaven, complete with a knowledgeable and approachable staff. Your quest ends with a house-made soda and a slice of pie at Spinning J.

For the group outing

West Montrose Avenue in North Center | N Damen Ave to Ashland Ave

Situated just south of Lincoln Square, North Center offers a well-rounded bounty of stores for the pickiest of shoppers. Start at lifestyle depot Neighborly, which is stuffed with funky gifts and decor. For those looking to splurge on something sparkly and special, book it to Mineralogy (1944 W Montrose Ave; 773-490-4233,, where rare stones are the name of the game. A quick trip to Cloud & Bunny (1600 W Montrose Ave; is a must for new parents looking to outfit their little ones in something exceptionally stylish. Now all you need to round out the trip is a beer on the rooftop at Fountainhead.


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