Is it any wonder that Chicago, a city with "chic" in its name, has so many unique boutiques? The surprising part is how much treasure you'll find in these shops on upscale Oak Street in the Gold Coast, hip Wicker Park/Bucktown, ever-charming Andersonville and posh Lincoln Park.
You can also find rare vintage goods at Chicago's various street fairs and pop-up events that set up shop in neighborhoods year-round, including the Randolph Street Market Festival, Renegade Craft Fair and Dose Market.
Score luxurious apparel, jewelry, shoes, and accessories right off The Magnificent Mile at Oak Street stores like Barney's New York, Lester Lampert, and Hermes Paris. In company with style-setters from around the world, you can shop the latest trends from designers who set the trajectory for fashion.
Make your way over to the Esquire Theater, a former movie theater turned retail heaven. Inside, you can visit Tom Ford to browse the collections of the famed American designer; discover the latest French fashions at Maje and Sandro; or admire the elegant pieces from Dolce & Gabbana. You can head next door to the high-end world of Carolina Herrera, or become the envy of your friends with some world-class jewelry from Buccellati.
Relax during your quest for the best at Oak Street spas offering services and pampering beyond your imagination. Refuel at any of a vast array of restaurants in this unparalleled luxury retail district.
Head a few blocks north to charming, tree-lined Lincoln Park where many shops are in Victorian row houses. On streets with names like Armitage, Halsted, and Webster, you can browse for everything from clothing for men, women, and children to shoes and adornments, home décor, stationery, gifts, and treats for your favorite pet.
Recharge at bars like Kincade's or eateries to suit any taste, from Nookies Too Lincoln Park for casual American food to world-renowned restaurants, and everything in-between.
This diverse area is home to several neighborhoods: East Lakeview, Central Lakeview, Boystown and Wrigleyville, each offering its own distinct vibe. Head to the bustling commercial districts along Belmont Avenue, Lincoln Avenue, Clark Street, Halsted Street and Broadway Street to shop — be it for retro jumpsuits, designer jeans, gourmet specialties or leather biker gear — and refuel at one of the many bars, pubs or celebrated restaurants.
Music enthusiasts can find their newest instrument at The Chicago Music Exchange, while art lovers will appreciate the vast selection at Art De Triumph and foodies revel in the cut-to-order domestic and international Partisan cheeses and freshly baked bread at Pastoral Artisan Cheese, Bread & Wine.
Also in Lakeview, just off the Southport Brown ‘L' Line stop, the Southport Corridor is a concentrated area of one-of-a kind stores, recognizable brands and outdoor restaurants offering a charming shopping experience.
Don't miss nearby Wicker Park and Bucktown, the eclectic area Vanity Fair pegged "a square mile of sassy boutiques." This shopping district encompasses the busy 6-corner intersection of Milwaukee, Damen and North Avenues, as well as Division Street.
Find beautiful accesories and clothing from local talent at Stitch and Michelle Tan, snag some contemporary menswear at Apartment No. 9 (for the bespoke look) and RSVP Gallery (for the urban look), or go more upscale with big-name designers like Nanette Lepore, Joe's Jeans and Marc Jacobs. Scoop up lovely gifts and home decor (Asrai Garden, Eskell) or prime vintage picks (Vintage Underground, Store B Vintage) or really anything you can think of... from rare sneakers to used cowboy boots, comic books to old records.
In this neighborhood, you'll find tons of excellent places to eat when you need a shopping break. Try the BBQ at Smoke Daddy, comfort food at The Southern Chicago, gourmet Italian at Lucia's Chicago, and delicious dishes and desserts at Mindy's Hot Chocolate.
Steeped in Swedish history and home to one of the city's largest gay and lesbian communities, this eclectic North Side neighborhood is the place to find everything from Swedish souvenirs and ethnic specialties to chic home décor and stylish fashions. Walk along Clark Street to explore the many indie boutiques and restaurants, and sign up for the Locals Supporting Locals — LoLo — loyalty program to get five percent back on purchases made at participating businesses.