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Your Chicago Holiday Bucket List

Posted on November 19, 2024   |   Updated on September 30, 2025
Sidney Madden

Sidney Madden

A Chicago holiday bingo card

We’re making the most of the holidays in Chicago. (Sidney Madden / City Cast Chicago)

Holidays in Chicago are almost as busy as summer, which is why we made this bucket list. Plus, if your fall gloom is turning into the winter blues, we think this bucket list will help.

Ice Skate

‘Tis the season for ice skating at Maggie Daley Park, Millennium Park, and neighborhood rinks. And if you’re not smooth on the ice, take a free lesson downtown on Saturdays to learn to skate or brush up on hockey skills.

CTA Holiday Train

All Aboard the CTA Holiday Train! (CTA / Flickr)

Ride the Holiday Train

Is there any better feeling than when the CTA holiday train unexpectedly pulls up? The city’s transit agency hasn’t yet released the schedule, but we’ll keep you posted when it does. Your last chance to book a Metra holiday train is today at noon for a Nov. 30 ride on the Metra Electric Line.

Sip Hot Chocolate

Hey Chicago readers know their hot chocolate: You all shared your favorite places to get the warm drink last year. I’m partial to Christkindlmarket, where you can take home a commemorative mug.

Catch a Holiday Display

The city’s 53-foot Colorado Blue Spruce comes from a Logan Square family. If you want to see lots of trees, head to the Museum of Science and Industry’s “Christmas Around the World” exhibit. If you’re into light shows, head to Lincoln Park Zoo, the Chicago Botanic Garden, Morton Arboretum, or different suburbs.

Volunteer or Donate

Want to give back? Help My Block My Hood My City decorate South Siders’ homes or pack meals at the Greater Chicago Food Depository. Donate toys or winter coats.

A Mariah Carey cutout at her holiday pop-up bar

Mariah Carey has a pop-up bar at the Virgin Hotel in the Loop. (Courtesy of Bucket Listers)

Visit a Holiday Bar

Make your own holiday bar crawl and visit Rudolph’s, 8 Crazy Nights, and Mariah Carey’s pop-up bar.

Shop Local

Why do your holiday shopping at big box stores when Chicago’s local businesses have unique gifts your friends and family will love? Block Club’s local gift guide just dropped, and we’re obsessed with everything from the plush plant toys to neighborhood baseball jerseys 😍

City Cast

Your Last-Minute Chicago Gift Guide

00:00:00

Touch Snow

It’s been a warm fall, but snow is in the forecast this week. Once it sticks, be sure to sled. Plus, guess who just learned you can ski and snowboard in nearby states like Wisconsin and Michigan?

We’ll keep you updated on our progress in the coming weeks as we check things off — and we hope you’ll keep us updated on yours, too!

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