The Chicago holiday season is beautiful, bombastic, and bountiful. There are so many Chicago holiday activities, from ice skating in Millennium Park to shopping at the Christkindlmarket that it can be both magical and overwhelming to experience, so let Bobby’s Bike Hike show you around!

When we think of the winter holidays, two things come to mind: festive decorations and an excess of food. You can’t celebrate the holidays with one and not the other, which is why our  Holiday Hike: Season Sampling Food & Walking Tour has both! But if holiday foods aren’t your taste, we do offer a Chicago’s Holiday Stroll – Walking Tour of the holiday

Even if it’s chilly outside, we know the places to go that’ll warm you up and show you how festive (and tasty) Chicago can be.

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

Chicago Holiday Festivals

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

Holiday Lights - Chicago Botanic Gardens Light tunnel

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“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

Christmas tree at Christmas around the world - Museum of Science and Industry

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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 

Zoolights at Chicago Lincoln Park Zoo - Chicago Christmas lights

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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

Chicago Christmas display - Holiday Tree at Macy's

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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.

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 

Ferris wheel and festival at Winter Wonderfest at Chicago's Navy Pier

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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

A Disney-themed Float at the Holiday Parade at Chicago's Miracle Mile

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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! 


Market stand full of lights at Chicago's Christkindlmarket - a traditional German Chicago Christmas market

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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. 

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.

group on chicago holiday stroll through downtown