Explore Chicago

The Best of Holiday Shopping in Chicago

We've compiled a list of five fantastically festive holiday shopping spots in Chicago.

It’s this time of the year when you can shop for yourself, your family and your friends. It’s that one time you can shop without feeling guilty. In Chicago, the choices are plenty. From vintage stores to high-end luxury boutiques, there is something that can meet your budget. There’s definitely something for everyone.

Five Holiday Shopping Options in Chicago

Chicago Fair Trade Holiday Pop-Up Shop

The Annual Chicago Fair Trade Holiday Pop-Up Shop returns this year and is open from November 1 to December 24. Items include trendy clothing, accessories such as jewelry, warm socks, toys, home goods, chocolate and coffee. There are good quality and quantity goods all under one roof. Located at 1457 N. Halsted Street, the shop is open from Tuesday to Saturday, 11:00 a.m. to 7:00 p.m., and on Sunday, 11:00 a.m. to 6:00 p.m. 

Courtesy Chicago Fair Trade Holiday Pop-Up Shop | WHERE Traveler®
(Courtesy Chicago Fair Trade Holiday Pop-Up Shop)

Renegade Holiday Craft Fair

The 2022 Renegade Holiday Craft Fair is open for two days only. It begins on Saturday, December 17 and ends on Sunday, December 18. This is an opportunity to support local businesses and shop for various gifts from many talented artists. You can find fashionable clothing, impressive and one-of-a-kind artworks and unique gifts at the Renegade Craft Fair.


The Christkindlmarket comes from a German and European tradition that showcases an international style with local appeal. Open from November 18 to December 24, Christkindlmarket exhibits high-quality gifts and food from vendors. It is an outdoor market that provides shopping, live entertainment, food and beverages such as mulled wine from Germany. The entire family will appreciate such a memorable experience. 

Christkindlmarket Chicago | WHERE Traveler®
Christkindlmarket (©Abel Arciniega/Choose Chicago)

One of A Kind Holiday Show

The One of A Kind Holiday Show returns to THE MART this year from Thursday, December 1 to Sunday, December 4. The Show will include 500 skillful artists, artisans and many more to bring shoppers the best of everything, such as homemade goods, gourmet items, fine art, live entertainment and fun activities. The One of A Kind Holiday Show provides plenty of quality goods and gift ideas, and it’s a place you won’t want to miss, even if it’s just window shopping.

State Street Holiday Market

The State Street Holiday Market is a festive event that celebrates local small businesses. Located in the heart of Chicago’s Loop, the market features talented artists and artisans from the Sundays on State series. There is something for everyone at this market, from unique holiday gifts to festive entertainment. So be sure to stop by and get in the holiday spirit! The market is open until December 18 on Fridays, Saturdays and Sundays from 11 a.m. to 6 p.m. 

Christmas Gifts | WHERE Traveler®
Christmas Gifts (©Isaac Martin)