The 5 Best Stops to Make in Chicago’s Trendy Wicker Park Neighborhood

For: A dose of culture

Curator Monique Meloche’s eponymous gallery is known for featuring up-and-coming artists working in all media types. Celebrated socio-political photographer Rashid Johnson has shown there, as has Cheryl Pope, a sculpture and installation artist who studied under Nick Cave. Currently, Amy Sherald’s A Wonderful Dream is on display—it’s a collection of compelling portraits of acquaintances or friends of the artist that explore race and identity.

2154 W. Division; 773-252-0299; moniquemeloche.com

For: A caffeine kick

This list wouldn’t be complete without a coffee shop (read: the ultimate hipster hangout). Since its recent opening in April, Americano 2211 has been garnering rave reviews for its perfectly poured espresso drinks. The white-walled, wood-accented, European-inspired café—a joint project from Chicago culinary stars Nancy Silver and Chris Pappas—shouldn’t be overlooked for its food offerings, either. Their all-day menu includes pearled barley salad and burrata with eggplant jam; they also make their own ice cream, like caramelized banana chocolate chip and grapefruit prosecco sorbet.

2211 W. North Ave.; 773-360-8757; americano2211.com

For: Nostalgia-inducing vintage shopping

At Kokorokoko, you’ll instantly be transported back in time via troves of ‘80s and ‘90s clothing, accessories, and knick-knacks. This vintage shop is one of the top-rated in Chicago, mostly due to its careful selection of items from those two epic decades. You can expect to find perfectly bleached mom jeans and flower-print crop tops amongst niche scores like neon fanny packs, Fila pullovers, and pastel-colored velvet scrunchies.

1323 N. Milwaukee Ave.; 773-252-6996; kokorokokovintage.com

For: An unforgettable dinner

Schwa, a Michelin-starred restaurant, offers the best of both culinary worlds: a casual, lively atmosphere with seriously inventive eats. Hip hop blares as the kitchen churns out seasonal nine-course dinners—head chef Michael Carlson’s current menu includes items like octopus and watermelon and unagi ice cream. Diners are encouraged to bring their own booze, which is often shared with the group (and the chefs, who also act as servers). Be warned: Reservations can be difficult to snag, so prepare to be flexible.

1466 N. Ashland Ave.; 773-252-1466; schwarestaurant.com

For: A late-night cocktail

This speakeasy-style cocktail bar is basically a Chicago institution. Expect a sexy, intimate feel—the bar features chandeliers and high-backed chairs, plus a sign that asks patrons not to use their cellphones. The cocktails are no joke, either; the menu changes seasonally and incorporates house-made syrups and bitters. This summer, try The Moonchild, a lychee-like martini with notes of peach, or the June & Henry, made with fresh sugar cane, La Favorite Rhum, and ancho chiles.   

1520 N. Damen; 773-252-1500; theviolethour.com