Lakeview

The ever-on-trend Lakeview shopping district centers along Belmont Avenue and Halsted and Clark streets. The people-watching mecca has some of the best discount shops, vintage finds and all-around eccentric clothing and accessory boutiques that Chicago has to offer.

Loop

Don’t let the Loop’s towering skyscrapers and business-like atmosphere keep you from shopping at this area’s big-name stores and hidden gems. Along with great architecture and some of Chicago’s most famous buildings, the Loop also has a famous shopping district, located primarily on State Street, where you’ll find stores like the historic Macy’s flagship (111 N. State St.), Nordstrom Rack (24 N. State St.) and Old Navy...

Magnificent Mile and Gold Coast

The Gold Coast offers a stretch of shopping opportunities for those who have a luxurious and expensive eye for fine fabrics and statement pieces. Start on the Magnificent Mile, which boasts a beautiful view of Chicago’s famous skyline, as well as a mixture of small, upscale shops and big-name stores. Wrap up your excursion on Oak and Rush streets to shop in splurge-worthy boutiques.

Wicker Park

Wicker Park has transformed over the years into one of the biggest up-and-coming fashion meccas in the city, if not the world. Holding its ground with other fashion-savvy Chicago neighborhoods, Wicker Park has a singular mix of vintage shops, record stores, national clothing chains and cutting-edge fashion boutiques.