Chicago doesn’t do the holidays halfway — we do them Chicago-style. That means over-the-top light displays, world-famous markets, and more hot cocoa than you can carry. Whether you’re a local looking to get into the holiday spirit or visiting for a winter getaway, this guide covers all the must-see holiday lights, markets, and festivals that make the Windy City shine.
And if you’d rather skip the planning and just enjoy the magic, let Bobby’s Bike Hike Chicago lead the way. Our Holiday Hike: Season Sampling Food & Walking Tour blends Chicago’s best bites, festive lights, and holiday history into one unforgettable experience — no mittens required (well, maybe a pair).
If you’re looking for holiday activities, here are our top recommendations for Chicago holiday light tours, holiday festivals, and local holiday markets.
Chicago Holiday Light Tours
- Lightscape at Chicago Botanic Gardens
- Christmas Around the World at the Museum of Science and Industry
- Zoolights at Lincoln Park Zoo
- Tree and Holiday Window Display at Macy’s
Chicago Holiday Festivals
- Winter Wonderfest at Navy Pier
- Lights Festival at The Magnificent Mile
Chicago Holiday Markets
Guided Chicago Holiday Tours
Chicago Holiday Light Tours
From Christmas to Hanukkah, holiday lights play an important role in holiday celebrations. Maybe that’s because it gets so dark in the winter! Whatever the reason, Chicago is excellent at using that nighttime backdrop to create dazzling displays of lights all over the city. Here are some of our recommendations for the best places to see the Chicago holiday lights!
Lightscape at Chicago Botanic Gardens
Photo from: https://www.chicagobotanic.org/lightscape
“Lightscape” is a holiday exhibit at the Chicago Botanic Gardens, and we love experiencing it each winter! Despite the name, the Chicago Botanic Gardens are technically located in the Chicagoland suburb of Glencoe, but even during normal days, they’re worth the trip. This after-dark experience is a mile-long trail of lights is jaw-dropping and makes for incredible pictures. Lightscape debuted in London in 2018 and had over 100 million visitors. We’re excited to catch it from November through January.
Christmas Around the World at the Museum of Science and Industry
Photo from: https://www.msichicago.org/explore/whats-here/exhibits/christmas-around-the-world/
It’s easy to see how your community celebrates Christmas, but have you ever wondered how Christmas is celebrated elsewhere? The Museum of Science and Industry’s “Christmas Around the World” exhibit represents Christmas holiday traditions from around the world with over fifty decorated trees. This exhibit opens in November and runs through January, so there’s no excuse to miss it!
Zoolights at Lincoln Park Zoo
Photo from: https://www.lpzoo.org/zoolights-presented-comed-and-invesco-qqq
The Lincoln Park Zoo is 35 acres large and offers free entrance every day of the year. During Christmas in Chicago, you can visit the animals and attend holiday-themed activities like ice sculpture carving. Their luminous holiday decor includes 2.5 million lights, and they even offer a special maze of lights! The Zoolights exhibit runs from November 29th to January 5th.
Tree and Holiday Window Display at Macy’s
Photo from: https://www.visitmacysusa.com/restaurant/walnut-room
Macy’s has become synonymous with holiday celebrations (who doesn’t love watching the Macy’s Thanksgiving Day Parade??). For Christmas in Chicago, you can watch Macy’s celebrate the holidays live and in-person! The downtown Macy’s location is known for its gigantic Christmas tree/holiday display, and on Saturday, November 2nd at 12 pm, you can celebrate the 112th annual lighting of that tree.
Celebrate the holidays the Chicago way!
Our Holiday Stroll – Walking Tour brings you face-to-face with the city’s most iconic decorations, historic landmarks, and seasonal traditions, all led by Bobby’s expert guides. Perfect for couples, families, and groups!
Chicago Holiday Festivals
Kanye may have rapped about “all of the lights,” but there’s more to the holidays than pretty twinkle lights! Check out these suggestions for various holiday festivals to attend here in Chicago.
Winter Wonderfest at Navy Pier
Photo from: https://urbanmatter.com/chicago/winter-wonderfest-navy-pier/
All year long, Navy Pier is listed as one of the top places to visit in Chicago. During wintertime, a trip to the Pier is even more imperative because of their Winter Wonderfest. Offering over 170,000 square feet of holiday attractions, you can go ice skating (indoors ’cause baby, it’s cold outside), go thrill-seeking on rides and giant slides, or interact with various holiday characters roaming around the Pier. Winter Wonderfest goes from December 6 to January 12, and tickets are roughly $28.
Lights Festival at The Magnificent Mile
If “Sex and the City” took place in Chicago, the Magnificent Mile is where Carrie and her gang would shop. In November, the Magnificent Mile gets even more magnificent with the holiday lights festival! Foodie favorites like Garrett Popcorn and Eli’s Cheesecake Company are giving out free samples, and there’s a huge parade that culminates with fireworks over the Chicago River!
Chicago Holiday Markets
Gift-giving is one of the five “love languages” identified by Gary Chapman, and the holiday season is all about expressing love in this manner. If you’re looking to pick up some fun and locally made gifts for those on your holiday shopping list, check out these Chicago Holiday Markets!
Christkindlmarket
Photo from: https://www.timeout.com/chicago/things-to-do/christkindlmarket-chicago
One of the most famous Chicago Christmas markets is the Christkindlmarket. Christkindlmarket Chicago is a German-style, open-air market that has delicious bratwurst, spiced wine, and roasted nuts for you to snack on while doing your Christmas shopping. Even if you don’t buy anything, the window shopping definitely gets you into the holiday spirit! The downtown location at Daley Plaza is open from November 15-December 24, and the location in Wrigleyville is open from November 22-December 31. There is no admission cost at either location.
Local Tip: Visit Christkindlmarket on weekday mornings to avoid crowds and get a clearer view of the handcrafted ornaments.
Randolph Street Market
Unlike the Christkindlmarket which is open for a long stretch of dates, the Randolph Street Market is only open on November 23/24 and December 14/15, so make sure you mark your calendar! With over 125 vendors, you’ll find the perfect holiday gift and have a great time doing so. Timeout Magazine called it the “Best Market in Chicago” and USA Today ranked it as one of the “10 best flea markets for finding vintage treasures.” Admission tickets are $8.
Alright you merry readers, we hope you enjoyed our guide to enjoying the holiday activities in Chicago! If you know of other festive things to do during the holidays in Chicago, let everyone know in the comments below!
And if you’re looking for a holiday activity that doesn’t take planning on your part, just show up and let the guides handle the itinerary – check out the Chicago-style Holiday Hike: Season Sampling Food & Walking Tour or the Chicago’s Seasonal Stroll – Walking Tour.
Tips for Enjoying the Holidays in Chicago & Planning Your Trip
Chicago during the holidays is pure magic but a little planning goes a long way. Whether you’re visiting for a weekend getaway or enjoying a staycation, here’s everything you need to know before you bundle up and hit the lights.
Best Time to Visit Chicago During the Holiday Season
Holiday festivities in Chicago typically run from mid-November through early January.
- Lights & Festivals begin in mid-November, with Lightscape, ZooLights, and Magnificent Mile Lights Festival leading the way.
- Markets & Food Events like Christkindlmarket and Randolph Street Market stay open through December (some into New Year’s Eve).
To avoid crowds, plan weekday visits in early December. You’ll still get all the holiday sparkle without the shoulder-to-shoulder crowds.
What to Wear in November & December in Chicago
Chicago winters can be chilly (and windy), but that’s part of the experience! Dress in warm layers, waterproof boots, gloves, and a cozy hat. Our walking tours operate rain, snow, or shine, so staying comfortable means you can focus on the fun (and the food!).
Getting Around Chicago During the Holidays
Downtown Chicago is one of the most walkable holiday destinations in the U.S.
- Public Transit: The CTA Red and Blue Lines connect most major attractions.
- Walking Tours: Our Holiday Hike: Season Sampling Food & Walking Tour and Holiday Stroll – Walking Tour cover key holiday stops within walking distance of Millennium Park and the Magnificent Mile.
- Ride-Share or Bike: For neighborhoods beyond downtown, taxis and Divvy bikes are convenient options.
Local Holiday Favorites
If you want to explore beyond the main attractions, add these local holiday hits to your list:
- Andersonville’s Winter Walk: Quaint, locally owned shops and Swedish holiday flair.
- Lincoln Square’s Holiday Cheer Crawl: Boutique shopping, live carolers, and hot toddies.
- Wrigleyville’s Winterland: Carnival rides, beer gardens, and festive pop-ups right next to the ballpark.
And remember — Bobby’s Bike Hike offers custom private tours for groups who want to explore Chicago’s neighborhoods, lights, and tastes their way. Contact us to plan a private holiday experience.
