Chicago’s West Town is a blossoming, not-to-be-missed neighborhood just steps from the downtown core. Wicker Park, Bucktown, and Ukrainian Village make up this quadrant of the city, and West Chicago Avenue is an up-and-coming boulevard that’s perfect for an afternoon of shopping and—of course—a little bit of dining.
Start at Study Hall, where you find bold and bright fashion. If that’s not your look, don’t shy away just yet. The style here is simple and streamlined at the same time. It turns out that the men’s and women’s clothing and accessories are quite grown-up—despite the shop’s name. There’s plenty that catches your eye at this Ukrainian Village shop ranging from carefully chosen jewelry pieces to a gorgeous selection of children’s books. The owners pride themselves on showcasing hard-to-find items that will make even the most travel-weary glad you spent an afternoon shopping in the neighborhood.
Head east on West Chicago Avenue, and then detour briefly south on Damen Avenue to Sprout Home. This garden store has only two locations: Chicago and Brooklyn. Its footprint may be tiny, however its reputation is anything but. As you step into this cozy shop, you’ll feel the energy from the bursting greenery. You can admire anything from tiny cacti to head-turning flower arrangements. It will be hard for you to walk away without a geometric vase or some terrarium accessories you didn’t know you needed.
Once your thumb has turned fully green, continue east on West Chicago Avenue to Paperish Mess. Its art gallery doubles as a shop. You’ll find local handmade wares from over 100 independent artists, ranging from jewelry to greeting cards to home goods. This is the place to pick up unique gifts from the Second City, such as a stunning Chicago skyline bangle or miniature mixed-media canvases painted by a local artist.
If an afternoon spent shopping in Chicago has worked up your appetite, consider a dinner at Homestead on the Roof, above Root’s Pizza. The charming farm-to-table restaurant sits among—what else?—a rooftop garden. Dine in the green outdoors or score a seat inside the romantic environs on a cool night. The food here is the epitome of fresh and seasonal fare. And save room for dessert next door.
West Town Bakery & Diner is loud from top to bottom, from its interior graffiti artwork to the flavors of its must-have sweets. You cannot leave this Ukrainian Village establishment without trying at least one cakeball. The melt-in-your-mouth orbs may change your life, especially the French toast and red-velvet cakes. You should strongly consider ordering a baker’s dozen. If your family and friends are lucky, you’ll bring some home. But it’s unlikely the yummy baked morsels will make it that far.