Vintage, trendy or both? Whatever your stylish preference is, Chicago is definitely a fashion-forward city and continues to emerge with a wide range of fashion and shopping events. You'll discover one-of-a-kind merchandise in stores, boutiques, and outlets scattered throughout the city's many diverse neighborhoods. 

From seasonal & pop-up events to year-round shopping markets, you can easily find the top shopping markets and fashion events on the calendar each year. Favorites on this list include the Randolph Street Market, an indoor/outdoor European-style gathering, and the expansive One of a Kind Show & Sale.

The biggest shopping events are the seasonal sales so don't miss the bargains and overflowing inventories that kick off Black Friday (the day after Thanksgiving in November) and continue until the New Year in January. Other big shopping sale events are spread throughout the year during U.S. holidays:

  • President's Day (February)
  • Memorial Day (May)
  • Independence Day (July)
  • Labor Day (September)

There's also Mother's Day each May and Father's Day each June, and the Back to School sales that start as early as August.

Now you know when to shop, but where to start? Chicago is a shopper’s paradise. The Magnificent Mile offers hundreds of top retailers including four separate vertical shopping centers. Oak Street is known for its upscale boutiques and specialty gift stores. State Street, located in the very heart of the city, is famous for landmark department stores and the Midwest's largest jewelry district. Armitage Avenue provides boutique shopping in the quaint tree-lined Lincoln Park neighborhood. Between the six corners of Damen, North and Milwaukee Avenues, Wicker Park/Bucktown delivers unique shopping adventures in a neighborhood that is known for its artsy and bohemian spirit, while nearby Division Street is another option. If it's a deal you are looking for, the suburban outlet malls are where you should plan to spend a day.