The past is revitalized in these trendy North Side neighborhoods.
Chicago Tour: Bucktown and Wicker Park
Credit: Kevin Dickert

Bucktown meets Wicker Park just north of the bustling intersection of Milwaukee, Damen, and North Avenues, yielding a hodgepodge of upscale boutiques and vintage shops; mom-and-pop eateries and high-end restaurants; dive bars and cocktail lounges; and art galleries and tattoo shops. You can feel the energy here. Walk any direction from the crossroads of Milwaukee, Damen, and North to experience the vitality of this area. On the corner sits Flats Iron Arts Building, which houses artists, studios, and galleries. Veer off the main street around Wicker Park the park, and you’ll find beautifully restored Victorian mansions, indicative of the care given to restoring the residences throughout the area. Off the beaten path, south of Division on Noble stands the stunning Holy Trinity Polish Church, exemplifying Polish Cathedral-style architecture, and a reminder of the area’s immigrant roots. This cool contrast of history and innovation makes the neighborhoods of Bucktown and Wicker Park one of the trendiest in Chicago.


Opened in 2005, this small, 26-seat restaurant sits on the edge of the Wicker Park neighborhood. Redesigned in 2010, the interior now features chrome-tipped light sculptures, ebonized black wood floors, and a mylar mirrored floating ceiling. Known for his artful presentation, chef/proprietor and Chicagoland native Michael Carlson creates a rotating menu using fresh, seasonal ingredients from around the world, including rare snail roe from the shores of France and locally-grown Midwestern produce. Diners are served by the actual chefs, who offer creations like the apple pie soup and the quail egg-filled ravioli.


Men’s and women’s accessories and bags, furniture, and ceramics sit side-by-side in this design-driven boutique. Inspired by Colette in Paris and New York City’s Takashimaya, Pamela Hewett opened Stitch in 1998 to share some of her favorite lifestyle trappings. Stocking everything from $16 bangles to $3,500 ottomans, the store promises eclecticism at varying price points. Favorite finds include Kooba handbags and Missoni robes, plus Fantome clocks and Lampe Berger candelabras (often hidden in the rear).

Hot Chocolate

A contemporary American restaurant and dessert bar in Bucktown, Hot Chocolate is the brainchild of Mindy Segal, a former pastry chef at Spago and a three-time James Beard Foundation nominee for Outstanding Pastry Chef in the Country. In an open dining room adorned with simple round mirrors, disk-shaped light fixtures, and chocolate brown hues, patrons begin with signature dishes like the macaroni and cheese made with gruyere and mammoth cheddar. Of course, the dessert selection is the primary focus, and it includes warm brioche doughnuts and seven kinds of hot chocolate, each served with homemade marshmallows.

George’s Hot Dogs

For over 60 years, this mom-and-pop shop has served American and Greek eats. Order a George’s hot dog, made Chicago-style with the traditional city garnish: pickle spear, neon-green sweet relish, chopped onion, yellow mustard, sport peppers, tomato, and celery salt. Save room for homemade baklava for dessert.


This delightful nonprofit boutique sells fair-trade and eco-friendly clothing, jewelry, housewares, and foodstuffs from artisans in more than 60 countries. Pick up a recycled messenger rice bag made by artisans in Cambodia or a Tornillo wood platter made by Peruvian carvers. Check its website for in-store events.


The smells of Cumin waft into the streets and beckon in passersby to taste Indian mainstays like tikka masala and vindaloo as well as less common Nepalese dishes like goat curry and chewra (flattened rice). Cumin has earned its popularity with the locals, as well as a Bib Gourmand designation from Michelin for its good value in 2012.

Myopic Books

One of Chicago’s oldest used bookstores and a Wicker Park institution, Myopic Books offers bibliophiles more than 80,000 editions, including some collectibles. Check its website for their Poetry Series, and on Monday nights, stop in for the Myopic Improvised/Experimental Music Series, a curated music event.