
The holidays are right around the corner, and with it comes a host of festive plans to enjoy in the city, from holiday Candlelight concerts to ice skating, Christmas lights tours and more. And as it’s gifting season, we’re all on the lookout for unique gift plans. Whether shopping at an indie artisan market or browsing one of the Chicago Christmas markets, this city has a ton of unique festive markets. We’ve rounded up some of our favorite happening this season!
Mini-One-of-a-Kind Holiday Market at All Together Now

One of our favorite holiday markets in Chicago is happening this Sunday, and it’s free! All Together Now is hosting a market featuring unique, locally crafted gifts from five beloved Chicago makers, perfect for finding unique presents. Enjoy a free welcome cocktail from Hoste Cocktails when you RSVP, and explore offerings from artisans like Ariadna Ginez, Exfolia, Happy Hour Shop, and Ruiz Atelier.
📍 Location: All Together Now, 2119 W Chicago Ave, Chicago, IL 60622
🗓️ Date: December 8th, 2-5pm
Festive Holiday Shopping in West Town

West Town Chamber of Commerce is set to launch its second annual “It’s a Wonderful West Town” holiday promotion from December 7th to December 24th. This expanded event celebrates local businesses and kicks off with a “Sip & Shop” extravaganza on December 7th. Shoppers can enjoy exclusive promotions and live carolers and enter to win giveaways by spending $25 at participating stores. Look out for snowflake vinyl decals and string lights marking the 25 participating businesses throughout the festive season.
📍 Location: West Town, Chicago
🗓️ Dates: December 7th – December 24th, 2024
Celebrate the Holidays at Randolph Street Market Festival

The Randolph Street Holiday Market Festival returns for its final market of the season on December 14-15, offering a unique holiday shopping experience in Chicago’s West Loop. This vibrant urban antiques market features over 125 top vintage dealers, designers, and makers, showcasing an array of vintage goods, fashion, and decor. Visitors can enjoy live DJ performances, local food vendors, and festive cocktails while exploring one-of-a-kind treasures. This year, the market is supporting Chicago Animal Care and Control, offering free entry with donations of pet-related items.
📍 Location: Plumber’s Union Hall, West Loop, Chicago
🗓️ Dates: December 14-15, 2024, 10 am to 5 pm
State Street Holiday Market

Head to the loop this weekend for the State Street Holiday Market. With over 85 small businesses set up for shopping, the new addition to Chicago Christmas markets is every weekend in December! Located indoors, a welcome reprieve from the chilly weather, the holiday market is on State Street, a celebrated shopping district in the Windy City. The weekend market is open Friday, Saturday, and Sunday from 11 a.m. to 6 p.m.
🗓️ Dates: Now—December 18, Fridays—Sundays
📍 Location: 35 S. State Street, Chicago, IL 60603
Christkindlmarket

We, of course, had to include the world one of the best Chicago Christmas markets on the list! During winter, annual traditions like Christkindlmarkt become our shining lights in times of darkness, early nightfall, and chilly temperatures. As Chicago’s notorious winter sweeps through the city, the festive season counters it with jubilance and cheer. Which made the absence of sipping Glühwein in Daley Plaza during the pandemic all the harder to swallow.
But worry not; Chicago’s German-inspired annual Christmas market is just around the corner after making a much-needed return last winter! The 26th edition of the beloved Christmas market will take over three locations across town.
🗓️ Dates: November 22—December 24
📍 Location: Daley Plaza, 50 W Washington St, Chicago, IL 60602
Chicago Artisan Market

The Chicago Artisan Market showcases the best of the Midwest in food, fashion, home goods, and art. Featuring vendors who are small businesses, the market highlights Chicago’s rich history as a “city that works.” Head to their holiday market in December to celebrate the creativity and passion of the local entrepreneurs!
🗓️ Dates: Sunday, December 15, 2024
📍 Location: 401 N Morgan St, Chicago, IL 60642