Offbeat Holiday Markets & Art Fairs

2025 Dovetail Holiday Market

This brewery features four weekends of live music, Santa visits, food, and more. Check their website for days and hours. 

Drie-Cember Market

This underrated holiday market is specifically curated and features vintage jewelry, handmade gifts, and elevated treats. 

Unusual Performances and Events

Try Cirque de Soleil for an alternative to traditional holiday performances. Photo by Errisson Lawrence

'Twas the Night Before by Cirque de Soleil

While the Nutcracker and It’s a Wonderful Life are classics, try a twist this year with a visit to a different type of performance. 'Twas the Night Before by Cirque du Soleil is running all of December, and it's a perfect holiday alternative. 

Black Ensemble's Holiday Spectacular. 

Featuring soulful renditions of Christmas classics, this kid-friendly musical revue is on stage during mid-December only. 

Unexpected Outdoor Adventures

Less crowded Ice Skating

The Chicago Park District has several public ice rinks open during the winter that tend to be quieter than downtown touristy spots. Try visiting Midway Plaisance, Warren Park, Mount Greenwood, or McFetridge Park. 

Hot Tub Boat River Cruise

That’s right. You and three family members can rent a hot tub boat for a two-hour cruise on the Chicago River. Remember to wear a hat! 

Illumination at the Morton Arboretum

Visit the Morton Arboretum for their holiday show, Illumination, which features light displays, music, and a s’mores pit. 

Candy Cane Lane Christmas Lights

Some neighborhoods go all-out this time of year, especially Candy Cane Lane, on the north side. Check out our guide on the best holiday lights in Chicago for families. 

Hidden Holiday Dining & Treats

Seasonal Milkshakes

Head to Jo Jo’s Shake bar for their take on the holiday. Kids can enjoy seasonal shakes, and there are also cocktails for the adults.

Igloo Dining

Try Rudolph’s Rooftop Winter Igloos on the roof of LondonHouse Chicago. Be sure to book ahead as spots fill around the holidays. 

Cozy Cultural Escapes

Candlelit Tours of Historic Homes

Try Pleasant Home in Oak Park or the Glessner House for their yearly candlelit tours.

Check out these over 50 internationally decorated holiday trees. Photo courtesy of the Griffin Museum of Science and Industry

Experience Christmas Around the World

Get global with Christmas Around the World at the Museum of Science and Industry. With more than 50 trees, this seasonal event highlights countries and traditions from around the world. 

Holiday Events at Local Libraries

Most libraries offer holiday story time or related holiday crafts. Head to your local branch to see what’s offered.

Wander through Lightscape before it ends. Photo courtesy of Chicago Botanical Garden

Lightscape at Chicago Botanic Garden

This immersive walking path and art installation features over 100,000 lights, making it a magical evening for all.