By Amy Tara Koch
August 12, 2014
Courtesy of Big Star

Not so long ago, a sojourn west on Division Street, past Caprini Green, was a dangerous proposition. Fast forward a decade and you’ve got one of the most buzzed-about neighborhoods in Chicago. Like most hipster hoods, the Bucktown/Wicker Park quadrant owns up to its hardscrabble heritage and uses grit to its advantage. A downtrodden Prohibition-era watering hole has become Double Door, a late-night institution. Epicurean feats are performed at The Trencherman, an of-the-moment eatery inhabiting a former Russian bathhouse. A few blocks over, Club Lucky is still slinging highballs (and killer lasagna) on its original gunshot-dinged bar while patrons are told the tale of how a mobster was popped off mid-martini. There may be no shortage of edgy boutiques and sleek coffeehouses, but this area’s cool barometer is the measured by the harmonious addition of dive bars and hot dog joints under the L tracks.

T-Shirt Deli

This quirky, custom T-shirt boutique is designed after an old school deli. Pick the style shirt you want, select your iron-on decal from dozens of options (images, logos, or letters) and hand it over to be whipped up while you wait. Shirts are packaged like sandwiches in white deli paper with chips.

Caffe Streets

Getting caffeinated beneath an undulating wooden ceiling and an audience of neon taxidermy definitely impacts your buzz. In the best way, of course. Founder Darko Arandjelovic, who also owns local coffee roaster Metric, is all about customization. Want Chemax? Eva Solo? Syphon? Baristas at this social coffee house will prepare your single origin brew any way you want.

Ruby Room Spa

This “spa for the spirit” focuses on near-mystical experiences that combine holistic add-ons with traditional therapies. Massages kick off with a chakra reading and facials often involve the use of crystals. The ground-level boutique stocks its namesake line of elixirs and detox salts, as well as hard-to-find beauty brands like Arcona.

Big Star

Under the shadow of the L sits Chicago’s reigning king of tacos; an always-packed 1950’s style diner serving up some of the tastiest Mexican street food-inspired fare in the city. With the affordable menu (nothing costs more than $10), indulge on a glass of whisky from the impressive reserve list. The tacos are my personal favorite: order the pork shoulder with grilled pineapple.

Helen Yi

Bucktown’s fashion pioneer, Helen Yi, has been quietly outfitting Chicago urbanistas for over a decade. Her minimalist aesthetic is the perfect backdrop for high-wattage silhouettes from designers like Barbara Bui, Costume National, and Derek Lam. Accessories, many of which are from local designers, are artfully suspended from sculptural wooden tree branches.