Chicago’s eclectic neighborhoods offer some of the world’s best dining, architectural landmarks, and art museums—and since its establishment, Wicker Park’s diverse cultural roots have made this neighborhood one of Chicago’s most vibrant. Named after brothers Charles and Joel Wicker, who donated a plot of land in 1870 for use as a public park, this charming area has been home to Ukrainian, Polish, and Puerto Rican communities—and, since the 1980s, to artists and creative entrepreneurs. Today, Wicker Park still exudes an atmosphere of “downtown cool” and what The New York Times describes as “an invigorating blend of reflection and reinvention.” From fine dining to locally owned boutiques, a weekend in Wicker Park offers a perfect staycation just off the Kennedy Expressway.
Filter Cafe | 1373-75 North Milwaukee Avenue
Chicagoans have always been coffee connoisseurs, and in Wicker Park there’s no cathedral to caffeine more revered than Filter. This usually bustling spot is tranquil in the mornings, when you might find yourself simply gazing at the mesmerizing “alley” mural on the ceiling; meanwhile, its ample seating and reliable Wi-Fi also make it ideal for sending off the last work email of the week. Pair a perfectly frothed latte with a mixed berry-topped parfait or the signature lox platter, before setting off for a day in the neighborhood.
Americano 2211 | 2211 West North Avenue
For a weekend brunch, lunch, or pastry and macchiato on the go, renowned pastry chef Nancy Silver’s recently opened restaurant is quickly becoming a neighborhood must-visit. Pastries like the cinnamon-hickory nut brioche and chocolatey cocoa-crème fraiche coffee cake are available all day to take out, but you can linger longer over dishes from their full Mediterranean-inspired menu, like the shakshuka or burrata with eggplant jam.
Schwa | 1466 North Ashland Avenue
Chef Michael Carlson helms this tasting menu-only establishment, which describes itself as a “kitchen where every ingredient is respected and every choice is intentional.” The minimalist-yet-cozy decor at Schwa, with bare pendant lightbulbs hanging above, allows the meticulously structured nine-course meal to take center stage. Menus are updated regularly to showcase seasonal foods and the versatility of the ingredients; recent highlights include unagi and watermelon, and a dish of snail, fresh pine, and earthy moss. Bring your favorite vintage to this BYOB establishment, but be sure to call ahead to secure a reservation.
Mildblend Supply Co. | 1342 North Milwaukee Avenue
This Wicker Park boutique keeps the fashion-forward denizens of Wicker Park on trend with a well-curated list of quality heritage brands and local and up-and-coming labels. Mildblend stocks men’s and women’s clothing, shoes, and accessories, with an extensive selection of raw denim brands, including 3sixteen, Eat Dust, and Nudie Jeans, and fine leather goods. The well-organized store has been a longtime supporter of the Made in USA movement, dedicated to retailing only high-quality and fairly sourced goods.
Urban Remains | 1850 West Grand Avenue
Unlike the typical eclectic flea market or antique store wares, the inventory at Urban Remains specializes in architectural remnants and artifacts recovered from historic Chicago buildings, some dating back to the 1800s. Get lost inside on a Sunday afternoon as you ponder whether to take home the streetcar swing stool from the line that ran down Milwaukee Street or the terra-cotta facade of a now-demolished Chicago garage.
Eskell | 1509 North Milwaukee Avenue
No shopping experience would be complete without a visit to this Wicker Park mainstay. Started by two friends, Kelly Whitesell and Elizabeth Del Castillo, Eskell is known for its house brand of clothing that channels the season’s trends through classic designs and wearable pieces. You can pick up a geometric gold pendant for yourself or a housewarming gift from its selection of housewares and bath and body products—or channel your inner James Dean with a new leather motorcycle jacket designed by Chicago-based label Straight to Hell.