By Tori Somsak

Chicago transforms into a winter wonderland every holiday season, glowing with festive lights, cozy markets, and classic city traditions that make the cold weather worth it. Whether you’re a lifelong Chicagoan or visiting for the first time, here are the best things to do in the city during the holidays.

1. Stroll Through the Christkindlmarket

No Chicago holiday is complete without a trip to the Christkindlmarket in Daley Plaza or Wrigleyville.

Why go:

• Authentic German holiday stalls
• Handcrafted ornaments and gifts
• Hot spiced wine (glühwein) in collectible mugs
• Pretzels, schnitzel, and chocolate treats

It’s crowded but charming, but go on a weekday if you can.

2. Experience ZooLights at Lincoln Park Zoo

One of Chicago’s most beloved traditions, ZooLights covers the entire zoo in millions of colorful lights and animated displays.

Highlights:

• Synchronized light shows
• Seasonal snacks and hot cocoa
• Special adults-only nights with cocktails

Plus, it’s affordable and family-friendly.

3. Go Ice Skating in the Loop

Chicago offers some of the most photogenic ice rinks in the U.S.:

• The Rink at Millennium Park: skate under the iconic Bean
• The Maggie Daley Skating Ribbon:  a winding path through winter scenery

Bring your own skates to save money!

4. Shop the Magnificent Mile Lights Festival

From Thanksgiving onward, the Magnificent Mile turns into a sparkling holiday shopping district.

Why it’s worth it:

• Hundreds of decorated storefronts
• Special sales and window displays
• Evening light shows and musical performances

Even if you’re not buying anything, it’s prime holiday sightseeing.

 

5. Warm Up With a Festive Holiday Meal

Chicago’s food scene goes all out for the holidays. Some must-try experiences:

• Holiday tea at The Drake or The Peninsula
• Cabin-themed pop-up bars like Rudolph’s or Frosty’s
• Seasonal tasting menus at top restaurants

Dine in a Private Heated Winter Dome:

• City Winery (Riverwalk & West Loop)
• Offshore Rooftop (Navy Pier)
• IO Godfrey

These feel like little snow globes with skyline views.

6. Catch a Classic Holiday Show

Chicago’s theater scene shines in December. Consider:

• The Nutcracker by the Joffrey Ballet
• A Christmas Carol at the Goodman Theatre
• The Christmas Pop-Up Bar Choirs at neighborhood venues

These shows sell out fast, so book early.

7. Take a Ride on CTA’s Holiday Train

A uniquely Chicago tradition—the CTA transforms one of its trains into a fully decked-out, glittering holiday express.

Expect:

• Santa waving from a decorated platform
• Holiday music
• Giant candy canes and twinkling lights

It’s whimsical, nostalgic, and makes commuting almost magical.

8. Explore Lightscape at the Chicago Botanic Garden

If you want a quieter, more immersive holiday experience, Lightscape is perfect. It’s a walking path through the gardens filled with glowing art installations and music.

Pro tip: Choose the earlier slots to avoid the biggest crowds.

9. Visit Macy’s on State Street

The historic Macy’s building becomes a holiday icon each year with:

• Elaborate window displays
• The giant Christmas tree inside the Walnut Room
• Classic holiday shopping vibes

It’s ideal for a wholesome  full festive experience.

10. Handmade Ornament Workshops

Local studios like:

• Lillstreet Art Center
• Fire Arts Chicago
• Ignite Glass

…offer glass-blowing or ceramics classes where you make your own ornament.

11. The Blackhawks “Holiday Night” Game

A themed game night with:

• special jerseys
• holiday graphics
•  fan giveaways

It’s niche but a vibe for sports fans.

12. Ring in the New Year Chicago-Style

Finish off the season by celebrating New Year’s Eve at:

• Navy Pier’s fireworks show
• Rooftop parties with skyline views
• Neighborhood festivities in West Loop or River North

The city lights up both literally and socially.