Chicago Seasonal Stroll Walking Tour of Holiday Attractions

There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through the Chicago Loop, Millennium Park, & the Magnificent Mile with an internationally recognized tour company proudly headquartered right here in Chicago. Our entertaining guides will spark your holiday spirit with fun facts, cultural insights, & the very best seasonal décor—like the surprising fact that Rudolph the Red-Nosed Reindeer was created in Chicago! Along the way, you’ll marvel at the iconic Christmas window displays of the original Marshall Field’s store, admire Chicago’s official Christmas tree, Mag Mile lights, and take in the festive Millennium Park ice skating rink. You’ll even enjoy VIP access—no waiting in line—to the legendary Christkindlmarket, the city’s beloved German holiday market. If you’re searching for Things to do in Chicago during the holidays, this experience is a perfect fit. Note: This is a walking tour only.

From: $0.00

Location: Chicago

What's Included

Walk beneath millions of glittering lights as the Magnificent Mile glows for the season.
Skip the Lines—enjoy festive, VIP front-of-line access to Christkindlmarket’s holiday magic.
Stroll through Millennium Park as it sparkles with lights and joyful holiday energy.
Watch skaters glide under the skyline as Millennium Park transforms into a holiday wonder.
Experience State Street’s festive shops bursting with lights, décor, and holiday cheer.
See Chicago’s soaring Christmas tree glowing with festive lights—pure holiday magic.
See the Wrigley Building glow with festive lights—an elegant icon shining bright for Christmas.
Join a lively local guide who brings Chicago’s holiday spirit to life with every story.
Marvel at Macy’s iconic holiday windows—sparkling scenes that capture pure Christmas joy.

Community Discussion

Q&A

Q: Is there a specific age limit for kids on this tour?

A: There's no strict age limit, but I’d say it's best for kids 5 and up. The walking might be a bit much for younger ones. Just be prepared to keep an eye on them, especially around busy areas like the Magnificent Mile. My kids loved it, though!

Q: What should I wear for this walking tour in winter?

A: Dress in layers! It can get really cold, especially when you're standing still to listen to the guide. I'd recommend a warm coat, gloves, and a hat. Good walking shoes are a must too, since you’ll be on your feet for a couple of hours. And don’t forget an umbrella just in case!

Q: Can you reschedule the tour if the weather is bad?

A: Yes, you can reschedule! The tour company is pretty flexible with weather-related cancellations. Just give them a call or email them, and they’ll help you find another date. But honestly, the holiday decorations in the snow can look really magical too!

Discussions

Thinking of gifting the Chicago Seasonal Stroll Walking Tour!

I'm planning to buy this for my sister's family for Christmas! It sounds like such a fun way to experience all the holiday vibes in Chicago. I love that you skip the lines at Christkindlmarket - that’ll save a ton of time! Can anyone share what the guides are like? Are they fun and engaging?

Just did the Holiday Walking Tour - Amazing experience!

I just got back from the Chicago Seasonal Stroll Walking Tour and WOW! The lights were absolutely stunning, especially the Christmas tree at Millennium Park. And skipping the line at Christkindlmarket was the best part! Highly recommend it for anyone looking to get into the holiday spirit. It was just 2 hours, but felt like the perfect amount of time. Definitely wear layers though!