Chicago Holiday Fun: My 2025 Guide to the Best Family + Adults-Only Events

Chicago is absolutely alive during the holiday season—and that’s exactly why I love this time of year. Whether you’re bundling up the kids, heading out for a date night, or grabbing friends for a festive evening, the energy in the city is electric. Lights, music, markets, cocktails, skating, surprises around every corner… this is Chicago at its best.

In the past, I’ve always shared my go-to round-up of the best places to see holiday lights—and don’t worry, that list is still one of my family’s favorites. But this year, I wanted to switch things up a bit. There is so much happening across the city beyond the traditional light tours, so I put together a new mix of both family-friendly fun and some of my favorite adults-only options for those elves who like to celebrate in full holiday spirit.

Below are 10 great ways to enjoy the season, complete with a little something for everyone.

⭐ Family-Friendly Favorites

1. CTA Holiday Train

This beloved Chicago tradition turns an ordinary commute into a magical ride. Santa’s sleigh literally rides the rails, the train is wrapped in lights, and kids absolutely light up from the moment the doors open.

2. Jack Frost in Fulton Market

Interactive and full of winter energy—think ice skating, bumper cars, curling, and endless photo ops. It’s an easy family outing and also a fun option for an early-evening date night.

3. Winter WonderFest at Navy Pier

Festival Hall transforms into an indoor winter playground with rides, slides, and activities. A perfect way to burn off holiday energy while staying warm.

4. Christkindlmarket Chicago

A classic for a reason. Handcrafted gifts, warm pretzels, hot chocolate, glühwein for the adults, and a festive European atmosphere that feels straight out of a holiday movie.

5. Winterland at Gallagher Way

The charm of Wrigleyville meets winter magic. You’ll find skating, holiday treats, games, and a neighborhood vibe that feels cozy and local.

6. Ice Skating at Millennium Park & the Maggie Daley Ribbon

Iconic skyline views, twinkling lights, and that unmistakable “winter in Chicago” feeling. The Ribbon adds a little adventure to your skating session with its winding path.

🍸 Adults-Only Holiday Fun

7. Elf’d Up (Wrigleyville)

Outrageous, hilarious, and fully Elf-themed—this pop-up bar is pure holiday joy for adults. Candy canes, themed cocktails, elf mugs, and plenty of Instagram-worthy moments.

8. Christmas Club Chicago

Three levels of holiday party energy. Great for groups, office holiday outings, or anyone who wants a festive night out in Wrigleyville.

9. I|O Godfrey Rooftop Igloos

One of my favorite date-night picks. Cozy heated igloos, beautiful city views, holiday cocktails, and that elevated Chicago rooftop vibe.

10. Frosty’s Christmas Bar

Over-the-top décor, DJs, dancing, and holiday cocktails. It’s a full-on party atmosphere perfect for getting your festive energy out.

Wishing you a warm, joyful, and wonderfully festive season ahead. Get out there and soak up every bit of Chicago’s holiday magic! 🎄✨