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11 Best Chicago Christmas Tours to Book This Year!
Have you been wondering about Chicago Christmas tours? You’ve come to the right place!
I’ve toured all the Christmas hot spots in Chicago–from the beautiful Christkindlmarket to the magnificent skating rinks downtown. I lived in Chicago (the city, not the suburbs) for over 16 years with my family.
During that time, we made sure to take part in all of the festive Christmas activities that this amazing city has to offer.
From going ice skating at Maggie Daley Park and enjoying hot cocoa in a custom Christkindlmarket mug, to walking tours of the Chicago Christmas tree and Macy’s holiday window displays, my family and I enjoyed every moment of it!
If you’ll be visiting Chicago this holiday season and you’re looking for a fun tour that will help you take in all of the best festive sights this wonderful city has to offer, then look no further!
I’m going to talk about the best Chicago Christmas tours designed specifically for those seeking to explore Chicago’s vibrant Christmas culture. You’ll get to experience all the wonderful things this city has to offer during this magical time of year.
So let’s jump in! 🎄
My Top 3 Picks: Chicago Christmas Tours
⭐️⭐️⭐️⭐️⭐️
Chicago Festive Food & Walking Tour
✅ Badge of Excellence Winner
✅ Sample tasty treats
✅ Wheelchair/stroller accessible
Chicago Seasonal Stroll Walking Tour
✅ Enjoy top tourist Attractions
✅ Wheelchair/ADA accessible
✅ Afternoon tour doesn’t impact dinner plans
Chicago Guided Walking Tour & Food Sampling
✅ Try Chicago favorites, like pizza and hot dogs
✅ Take photos with Chicago’s Christmas tree
✅ Adults can upgrade to a VIP (alcoholic) drink package
Note: Every tour in this article is a seasonal offering. Most are only available from November to December. So if you’re looking to book and it says it’s unavailable, fear not! Just check back closer to Christmas. 🎄
Best 5 Chicago Christmas Tours
1. Holiday Hike Chicago-Style: Festive Food & Walking Tour
⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 3 hours | ✅ Book Now!
Holiday Hike Chicago-Style: Festive Food & Walking Tour is an amazing Chicago Christmas tour that will make you feel like you stepped into a winter wonderland. Stroll through the city’s streets, lit up for the holidays, and take in the holiday spirit.
You’ll learn about Chicago’s unique and celebrated holiday traditions such as the European-inspired Christkindlmarket, decorated State Street windows, and ice skating at Millennium Park.
As you walk around the city, enjoy generous samples of classic Chicago foods like hot dogs, deep-dish pizza, and brownies (invented at Palmer House Hotel!) as well as delicious holiday treats.
Explore Europe-style holiday markets at Christkindlmarket, see the iconic outdoor ice skating rink at Millennium Park, and admire the gigantic Christmas tree display lit up for the season – these are just some of the highlights of this special tour.
It was a great experience! Josie did an excellent job leading us through the city and giving us all kinds of facts with a touch of humor. Would highly recommend this food tour!
tessa h (read more Reviews)
🔑 Key Essentials
☑️ Local tour guide
☑️ Food samples and holiday cocoa or cider included
☑️ Restaurants are pre-booked to avoid wait times
☑️ Maximum 15 travelers
☑️ Wheelchair accessible
☑️ All ages welcome
2. Chicago Seasonal Stroll Walking Tour
⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 2 hours | ✅ Book Now!
Explore Chicago’s top tourist attractions in a personalized and festive way this Winter season on an afternoon stroll walking tour. Experience all the wonderful sights together with friends and family – it’s sure to be an unforgettable adventure!
From admiring sights like Millennium Park, the Chicago Theater, and more, you’ll also visit the city’s Christkindlmarket, see Christmas window displays, explore ice rinks, and other winter-specific activities.
Come bundled for the chilly weather and receive a warm welcome from your experienced guide who will point out all of the big and small landmarks that make up this vibrant city.
Wander through the spectacular Christkindlmarket or shop for unique gifts at exclusive holiday stores. Make sure to take some time to appreciate the enormous Christmas window displays. They’re a perfect backdrop for a family photo!
[Our guide] was so fun and full of interesting facts about Chicago…Even thought the weather wasn’t great, the tour was so fun!! We appreciated her and her enthusiasm!
marlis b (read more Reviews)
🔑 Key Essentials
☑️ Local tour guide
☑️ Wheelchair and stroller accessible
☑️ 15 participants maximum
☑️ All ages welcome
3. Chicago Guided Walking Tour & Food Sampling
⭐️ RATING: 4.8/5 Stars | ⏳ TOUR LENGTH: 3 hours | ✅ Book Now!
Chicago Guided Walking Tour and Food Samples is the perfect tour for those looking to experience Christmas in Chicago in an unforgettable way.
Start with a brisk walk around Millennium Park, home to the iconic Christmas tree and ice-skating rink.
You’ll stop by various points of interest as your guide provides you with insights on the culture of the city. And don’t forget to warm up with complimentary hot apple cider!
Next, visit the historic Palmer House Hotel, where you will sample the original brownie – a local treat that’s been around since 1893. You’d be remiss not to try some Chicago pizza or hot dogs while on this tour!
If you’re looking for something extra special this holiday season, consider upgrading your Chicago Guided Walking Tour and Food Samples package to include a VIP Christmas adult beverage sampling package (extra fee).
Nate our tour guide is why this tour was amazing!…You can’t go wrong with Chicago’s iconic staples. Take the tour! You’ll love it!!
maribeth (read more Reviews)
🔑 Key Essentials
☑️ Food and non-alcoholic drinks
☑️ Local tour guide
☑️ VIP drink package upgrade (offered to adults upon arrival)
☑️ All ages welcome
4. Chicago’s Holiday Sights Pedway System Walking Tour
⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 2.5 hours | ✅ Book Now!
Join an amazing small-group walking tour through Chicago’s renowned Pedway! Discover hidden treasures beneath the bustling streets and delve into the fascinating history of this underground marvel.
Marvel at the iconic Tiffany Dome and conclude your adventure at one of Chicago’s beloved sculptures.
This carefully curated tour offers a personalized experience, making it easy to navigate the Pedway while enjoying the splendor of the city’s landmarks.
Visitors love being able to experience the Chicago pedway, which most tourists never even know exists! It’s the best of Chicago in one comprehensive tour. You don’t want to miss it!
Tom was very knowledgeable and personable. He tailored the tour to meet our needs. I highly recommend his tour.
Kim s (read more Reviews)
🔑 Key Essentials
☑️ Starts & Ends at the Cloud Gate (aka: Chicago Bean)
☑️ Local expert guide
☑️ Transit tickets included
☑️ 10 participants max
☑️ All ages welcome
5. Christmas Tree Crawl: Experience Chicago at the Holidays
⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 2 hours | ✅ Book Now!
Embark on a captivating and enlightening journey as you explore downtown Chicago on a nostalgic and educational “Christmas treasure hunt.”
Explore the city’s streets adorned with magnificent Christmas trees and festive decorations. This tour is packed with insider knowledge on where to find them all!
Experience iconic attractions like the Christkindlmarkt and the historic Marshall Field’s as well as hidden gems showcasing enchanting holiday displays in the heart of downtown.
Immerse yourself in the origins of beloved Christmas characters, both local to Chicago and from around the world. Delve into the rich history of Christmas traditions celebrated globally.
This was our first tour with Hillary and it was amazing! She was on time, informative, and so fun!…Thank you Hillary for a magical night!
tripadvisor reviewer (read more Reviews)
🔑 Key Essentials
☑️ Local expert guide
☑️ Snacks provided
☑️ 20 participants max
☑️ All ages welcome
☑️ Tour will be canceled with refunds for inclement weather
6. 2-Hour Chicago Holiday Lights Segway Tour
⭐️ RATING: 4.5/5 Stars | ⏳ TOUR LENGTH: 2.25 hours | ✅ Book Now!
Experience the enchanting holiday spirit of Chicago as you effortlessly explore iconic landmarks on a captivating Segway tour.
Glide through Millennium Park, immerse yourself in the bustling Loop, and marvel at festive displays along Michigan Avenue. Indulge in hot chocolate and ‘bratwurst’ beneath the majestic Christmas tree.
This unforgettable night tour is filled with dazzling lights and joyful festivities, offering a personalized experience for small groups.
Your guide will share insights about the rich history and iconic sights, making it an extraordinary journey through the holiday wonders of the Windy City.
This was our first time to Segway and Shawn made it a great family experience. We learned some fun and interesting Chicago history while we saw all the holiday lights throughout the city.
Karen g (read more Reviews)
🔑 Key Essentials
☑️ Professional guide
☑️ Thorough segway training and orientation
☑️ Explore the Christkinlmarket
☑️ Helmet and personal storage bag on Segway PT
☑️ 8 participants maximum
☑️ Participants must be ages 12+
7. Christmas Eve Gourmet Dinner Cruise on Lake Michigan
⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 2.5 hours | ✅ Book Now!
A Christmas Eve Gourmet Dinner Cruise on Lake Michigan is an incredible way to experience the holiday season in Chicago! If you want city lights cruises Chicago, then this is the Christmas vacation tour for you!
This luxurious cruise provides spectacular views of the city’s iconic skyline, complete with its historic Navy Pier, Grant Park, Willis Tower, 360 Chicago, and the Museum Campus.
During the tour, you’ll dine at a private table on a delicious 3-course plated dinner that’s served by professional staff. To top off the evening, enjoy a live DJ in a sophisticated setting to provide unforgettable music.
This Christmas Eve tour presents visitors with everything they need for an unforgettable holiday experience – beautiful views of the cityscape, incredible food and drink options, and excellent service.
It’s a really unique Christmas Eve in the Windy City!
Perfect sightseeing, music, service, and foods! I made a unforgettable memories though this trip!
get your guide traveler (read more Reviews)
🔑 Key Essentials
☑️ 3-course plated dinner
☑️ Onboard DJ entertainment
☑️ Unlimited coffee, hot tea, and iced tea
☑️ Local taxes and fees included
☑️ Kids under 2 are free
☑️ All ages welcome
☑️ Semi-formal attire encouraged
Other Chicago Christmas Holiday Tours
These holiday light tours are generally bookable closer to the holiday season in Chicago, especially the Chicago Trolley Tour which doesn’t generally publish its holiday tours schedule until at least November.
8. Chicago Holiday Fireworks Cruise
9. Free Tours by Foot Chicago Holiday Tour
10. Christmas Eve Plated Brunch Chicago River Cruise
11. Chicago Trolley Holiday Lights Tour
Christmas Tours Chicago Travel Tips
The ideal time to explore the city’s attractions and famous landmarks is during the holiday season when Chicago truly comes alive with festive spirit. There are Christmas lights tours galore!
One must-visit destination is Millennium Park, where you can witness the iconic Christmas tree and enjoy ice skating at the McCormick Tribune Ice Rink.
Another must-see is the Lincoln Park Zoo Chicago holiday lights tour, a dazzling display of Chicago Christmas lights and decorations that will captivate both kids and adults alike. Plus, on certain days of the week it’s a free Chicago Christmas lights tour!
And don’t miss the Magnificent Mile Lights Festival, a stunning spectacle of twinkling lights along Chicago’s famous shopping district.
If you’re lucky enough, you may even get to ride the Chicago Holiday Train or Holiday Bus if you take public transit around the city. Don’t drive if you can avoid it. Parking is difficult and pricey.
When preparing for your Chicago Christmas tour, remember to pack essential items such as warm clothing, gloves, scarves, and hats to stay cozy in the chilly weather.
Wear comfortable shoes as you’ll be doing a fair amount of Christmas lights walking.
Restroom facilities are available in various locations throughout the city, including parks, malls, and restaurants, so you won’t have to worry about finding a restroom when needed.
Chicago offers plenty of family-friendly activities during the holiday season. We love the Winter Wonderfest at Navy Pier, featuring indoor ice skating, carnival rides, and festive entertainment for the whole family to enjoy.
If you’re flying in, Chicago has two major airports, O’Hare International Airport and Midway International Airport, both offering a variety of flight options.
Once in the city, you can utilize public transportation, such as the CTA trains and buses, to navigate between attractions. Taxis and ride-sharing services are also readily available.
🤩 Holiday Hike Chicago-Style: Festive Food & Walking Tour because you get holiday snacks and sightseeing without having to wait in any lines! 🤩
Final Thoughts: Chicago Christmas Tours
Chicago Christmas tours are the perfect way to celebrate the holidays in the Windy City.
Whether you’re looking for a thrilling nightlife adventure or an intimate celebration with family and friends, there’s a holiday tour for everyone in Chicago.
This list of amazing Christmas events is sure to provide you with unforgettable memories that will stay with you long after the holiday season has passed.
So if you want to make this Christmas season one to remember, grab your tickets today and join us on an exciting festive tour of Chicago!
With enough exploration and wonder for everyone, these Christmas tours are guaranteed to make your holiday extra special.
I hope you love touring Chicago’s festive sights as much as I do. Christmas is my favorite time of year in Chicago!
FAQs About Christmas Tours in Chicago
Do you still have questions about Christmas tours in Chicago? Here are answers to some frequently asked questions.
Is Chicago a good place to spend Christmas?
Yes, Chicago is a great place to spend Christmas! From the city’s iconic Christmas markets to the Christkindlmarket at Daley Plaza to Magnificent Mile Lights Festival, there’s something for everyone.
And don’t forget the festive foods like gingersnaps and hot apple cider!
Is Chicago decorated for Christmas?
Yes, Chicago goes all out for Christmas! Throughout the city, from downtown to neighborhoods like Wrigleyville and Logan Square (home to the Chicago holiday house!), you’ll find lights and decorations.
During the holiday season, the iconic Magnificent Mile features an extravagant light show of more than a million twinkling LED lights and festive music that runs along North Michigan Avenue.
The area around Millennium Park is also decked out with a beautiful 100-foot-tall tree in addition to dazzling light displays and decorations.
What Christmas movie takes place in Chicago?
Home Alone is a classic Christmas movie that takes place in Chicago. The movie has become an iconic holiday favorite, with many memorable moments like Kevin setting booby traps around his house and the famous scene where he yells out “Merry Christmas ya filthy animal”.
Does it usually snow in Chicago in December?
Snowfall in Chicago is highly variable in December. While it does snow sometimes and even sometimes quite heavily, there is no guarantee of a White Christmas.
Most years, the city sees one or two significant snow storms that can bring accumulations of 6 inches or more, but these are usually interspersed with periods of warmer weather.
Is Chicago fun in the winter?
Yes, Chicago is a fun place to be in the winter! It’s home to world-class restaurants, lively music venues, and plenty of outdoor activities. The city is also filled with holiday cheer during this season, with lights adorning the streets and sights like Navy Pier’s Winter WonderFest.
You can go ice skating at Millennium Park or Lincoln Park Zoo, explore the neighborhood lights displays in Logan Square, or enjoy stunning views of the skyline from Willis Tower.
Read More:
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👉 Halloween Activities with Kids in Chicago
👉 Best Ice Cream in Chicago
👉 Top Places to Buy Paczki in Chicago on Fat Tuesday
👉 Awesome Things to Do on St. Patrick’s Day in Chicago
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