[Chicago] Year-Round Chicago Shopping markets & Fashion events



Maxwell Street Market
800 S. Desplaines St.
Every Sunday, Year-Round

Find global goods, collectibles and international cuisine — think Mexican and Latin street food like tacos and elotes — outside along the stalls of Maxwell Street Market every Sunday from 7 a.m. to 3 p.m. Discover local music artists at the market’s upcoming performances each week.

Randolph Street Market
Plumbers Hall (1340 W. Washington St.)
Monthly, Year-Round

Venture through the monthly Randolph Street Market to discover all sorts of seasonal goodies. During the colder months, find the market conveniently located at the three-level Plumbers Hall to make room for the 75-90 vendors, here to satisfy your antique, modern and vintage desires. For warm weather, experience all eight acres of this European-style, urban antique market with over 200 vendors featuring vintage and antique novelties, exceptional décor, valuable vinyl and global treasures. Come for the shopping and stay for the eats, drinks, and live entertainment.





Dose Market
Dates & locations vary, check website
Meet some of Chicago’s most exceptional chefs, makers, artisans, bakers and artists. Held seasonally throughout the year — often around top shopping holidays like Valentine’s Day, Mother’s Day and Christmas — these pop ups are expertly curated and have a hip, bohemian flair. They also set up shop in some of the city’s coolest spaces, like boutique hotels and industrial warehouses turned into special event venues. Come prepared with a gift list: takeaways range from scented candles and handcrafted soaps to jewelry and luxe sweaters.

Sauced Night Market
Dates & locations vary, check website
Sauced is a roving night market dedicated to emerging culinarians and artists — an evening of food, art and entertainment. Sauced pops up from the underground once a month to make your nights more interesting.

Vintage Garage Chicago
5051 N. Broadway
Every Third Sunday of the Month (April through October)

Get pumped for the best selection of vintage finds in Chicago! Search through midcentury modern steals, vintage clothing and jewelry, antique toys, valuable décor and furniture, unique artwork, and more. Explore the thrifty world of Vintage Garage Chicago for only $5 admission. Bonus: Each month there is a new theme to take part in, from Rockabilly Tiki to Retro!

Do Division Fashion & Sidewalk Sale
Division St. and Damen Ave.
Annually in June

This fashion fest-within-a-fest is dedicated to the latest styles from West Town and the surrounding Chicago area. A who’s who of local designers and merchandise, the highlight is the featured runway shows. Also throughout the weekend, Division Street’s independently-owned boutiques, salons and shops pop-up on Division’s extra wide sidewalks, giving way to 10 blocks of the best deals of the season for festival shoppers.

Renegade Craft Fair
Division Street between Damen and Ashland
Annually in September

Support the top independent makers and creators around from the DIY community. Renegade Craft Fair returns to Wicker Park each year for a jam-packed weekend of creativity. Along with shopping, guests can participate in DIY workshops and explore installations. Check out the Renegade Craft Fair website for occasional pop up events as well, usually held before the Christmas holiday.

Daley Plaza (50 W. Washington St.)
Annually from November to December 

Fröhliche Weihnachten! The Christkindlmarket is the largest open-air Christmas festival in Chicago. Collect traditional Christmas decorations, enjoy diverse holiday entertainment, and munch on delicious German treats at this highly anticipated festival. Celebrate this famous Chicago holiday extravaganza, now over 20 years running!

One of a Kind Show & Sale – Holiday
TheMART (222 Merchandise Mart Plaza)
Annually in December

The annual One of a Kind Show, Holiday Edition, is the perfect place to find unique holiday gifts for yourself and loved ones. For over 15 years, more than 600 talented artists from North America fill the massive Merchandise Mart halls with their handmade work, happily speaking one-on-one with shoppers to explain their craft and help them find just the right item. Enjoy artist demonstrations, fashion shows, and live music; gourmet cafés can be found throughout the show for refueling. Also regularly on the calendar is the spring edition of the One of a Kind Show & Sale, making for two times the opportunity to shop!