Cool Destinations
Top Illinois activities
Top Illinois landmarks
Beyond Illinois
Illinois trip ideas
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Tours by the numbers
  • Top Illinois landmark tours
  • Tours in nearby places
  • Explore USA tours
  • Illinois travel guides
  • Illinois travel calendar
Language $Currency
Login / Sign up
Bookings
Bookings
Cool Rewards Rewards
$0.00
Cool Rewards Rewards
$0.00
Wishlists
Wishlists
Profile
Help Center
Language
Log out
Start your search
Change your search
Place or activity
Select Dates

Top Illinois Christmas

6 Results
Sort by:
Featured
Filter
Languages Clear
Time of Day Clear
3
5
2
Duration Clear
0
6
0
0
0
Price Clear
$0 $500+
Rating Clear
6
6
6
Specials Clear
6
0
0
3
0
Features Clear
1
2
6
0
5
0
Accessibility Clear
2
3
5
Families Clear
4
4
1

Illinois Tours

Attractions

Guides

Calendar

Historical and Architectural Chicago Fireboat River & Lake Cruise
Chicago, USA
4.9 (455)

Historical and Architectural Chicago Fireboat River & Lake Cruise

Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel on Lake Michigan and through the Chicago River seeing...

2 hours • Free Cancellation
4.9 (455)
from
$47
The Christmas Tree Crawl Experience Chicago at the Holidays
Chicago, USA
4.9 (44)

The Christmas Tree Crawl Experience Chicago at the Holidays

On this nostalgic and educational tour, we will lead you on a "Christmas treasure hunt" through downtown Chicago in search of the most stunning and...

2 hours • Free Cancellation
4.9 (44)
from
$35
Chicago-Style Holiday Hike: Festive Food and Walking Tour
Chicago, USA
5.0 (77)

Chicago-Style Holiday Hike: Festive Food and Walking Tour

There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holiday Hike, a 3-hour guided...

3 hours • Free Cancellation
5.0 (77)
from
$85
Chicago Seasonal Stroll Walking Tour of Holiday Attractions
Chicago, USA
5.0 (5)

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...

2 hours • Free Cancellation
5.0 (5)
from
$45
Private Holiday City Tour
Chicago, USA
5.0 (3)

Private Holiday City Tour

Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal...

3 hours • Hotel pickup offered • Free Cancellation
5.0 (3)
from
$499
Private Christmas Walking Tour in Chicago with Christkindlmarket
Chicago, USA
5.0 (1)

Private Christmas Walking Tour in Chicago with Christkindlmarket

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where architectural landmarks are...

2 hours • Free Cancellation
5.0 (1)
from
$469

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
It was fine but went way...
New York City
Historical and Architectural Chicago Fireboat River & Lake Cruise
gail_B, Sep 2026
It was fine but went way...
It was fine but went way over return time dock. Had to reschedule our dinner reservations twice. Kids hanging around left side of railing and got a little loud hard to hear the speaker.
Read more
Exceptional
New York City
Historical and Architectural Chicago Fireboat River & Lake Cruise
Patricia_S, Sep 2026
Exceptional
This was the highlight of our weekend to Chicago. We couldn’t have asked for a better experience. The weather was gorgeous, and the staff were tremendous. Our guide was exceptionally knowledgeable about the history and architecture of Chicago, was entertaining, and friendly. Should we ever have a chance to revisit Chicago in the future, I would definitely book this experience again.
Read more
A well-organized and unique cultural experience
New York City
Private Christmas Walking Tour in Chicago with Christkindlmarket
emiliacosmo88, Jan 2026
A well-organized and unique cultural experience
As a visitor, I was captivated by the charm of the market which has so many uniquely decorated stalls and plentiful food options. Overall, this tour was holiday cheer and unique cultural experiences all in one place.
Read more
Amazing time
New York City
The Christmas Tree Crawl Experience Chicago at the Holidays
f0ntanezr, Jan 2026
Amazing time
We booked The Christmas Tree Crawl Experience in Chicago through Cool Destinations on December 13, and we had amazing time. The tour was enjoyable regardless of the cold and windy weather indicative of the season, thanks to the excellent knowledge of our guide, Hillary, who combined insight into architecture and history with her outstanding knowledge of Christmas traditions to create a memorable tour experience. We are planning to return next year.
Read more
A must do!
New York City
Chicago-Style Holiday Hike: Festive Food and Walking Tour
Julia_W, Dec 2025
A must do!
Great experience, will recommend to all of our friends. Great combination of favorite Chicago foods. Fran was an incredible guide!
Read more
Private Tour
New York City
Private Holiday City Tour
oseasd2020, Dec 2025
Private Tour
The private tour was great! Our guide Mr. Matthew and driver Victor were very friendly and helpful. We enjoyed every stop and learning about the Chicago culture . I recommend.
Read more
Ask for Gabe
New York City
Chicago Seasonal Stroll Walking Tour of Holiday Attractions
erica_t, Dec 2025
Ask for Gabe
Holiday sights, history, and architecture information included in an easy walk. Tour guide Gabe is knowledgeable and entertaining. Highly recommend.
Read more
A totally delightful, festive tour
New York City
The Christmas Tree Crawl Experience Chicago at the Holidays
Eric P, Dec 2025
A totally delightful, festive tour
My sister and I spent a few days in Chicago right before Christmas, and we did this tour on a lark… And it was absolutely delightful. It’s an inside and outside walking tour of downtown, highlighting all kinds of Christmas decorations. Hilary (who also happens to own the company) was a fantastic guide – knowledgeable, fun, super warm, and full of historical and architectural information along with the festive Christmas stuff. Completely, utterly delightful.
Read more
No need for breakfast!
New York City
Chicago-Style Holiday Hike: Festive Food and Walking Tour
Richard A, Dec 2025
No need for breakfast!
Surprisingly large amount of good but not amazing food (standard Chicago fare, not a foodie’s paradise), but it was our guide Fran that really made it special with her friendly “mom-like” demeanor and interesting stories about the points of interest along the way. The final stop Christkindlmart was absolutely mobbed despite Monday afternoon at 2:30 (on 12/22 tho); at least she had a skip-the-line entrance to get in. Overall we were very pleased we did it.
Read more
Christmas in Chicago
New York City
Private Holiday City Tour
christine_g, Dec 2025
Christmas in Chicago
Matt and Vick were AMAZING!! The diversity, knowledge, and understanding was one of a kind and know I couldn't find it anywhere else. It was chilly out today but the vehicle was warm and comfortable. The uniqueness of Chicago which makes this city so monumental and the truth inside the bean! We are so happy we took those tour and blessed Matt and Vick were our tour guides and driver!
Read more
Chicago Fire Boat Tours
New York City
Historical and Architectural Chicago Fireboat River & Lake Cruise
Richard_M, Sep 2026
Chicago Fire Boat Tours
Excellent day! Crew was great and provided not only architectural information but also history about Chicago.
Read more
The best boat tour in Chicago!
New York City
Historical and Architectural Chicago Fireboat River & Lake Cruise
E6735MXnickf, Sep 2026
The best boat tour in Chicago!
What a wonderful way to spend a couple of hours. Cliff and the entire team take you on an informative and relaxed cruise around Chicago. Highlighting historical moments, amazing architecture, and important landmarks of the Chicago skyline. We have been on other river tours, but this one is just on another level. The boat itself is a piece of Chicago history and will definitely remember the great tour and the people that run it!
Read more
A Festive Delight
New York City
The Christmas Tree Crawl Experience Chicago at the Holidays
Eric_P, Dec 2025
A Festive Delight
My sister and I did this while in Chicago for a few days. It was so fun and charming and festive. Hilary (who actually owns the tour company) could not have been more knowledgeable - and she’s a freaking delight. The tour ends at the Palmer House, which is a gorgeous, historic hotel (super festive at Christmas). Fantastic guide, fantastic tour!
Read more
Fran our guide was awesome and very knowledgeable.
New York City
Chicago-Style Holiday Hike: Festive Food and Walking Tour
Melvin_W, Dec 2025
Fran our guide was awesome and very knowledgeable.
Need a good appetite and walking shoes. Very scenic never knew anything about underground center. Would highly recommend.
Read more
Downtown Chicago Christmas Vibes
New York City
Chicago-Style Holiday Hike: Festive Food and Walking Tour
Aschmid84, Dec 2025
Downtown Chicago Christmas Vibes
This is an absolute must of your in Chicago!! The amount of information, the good vibes, good food. Gabe, our tour guide, was very knowledgeable, great personality, very interactive, just all around good guy. I swear if we didn't do this, our trip would have been completely different.
Read more
Well-run tour that our kid enjoyed! Comfortable pace that shows so much!
New York City
The Christmas Tree Crawl Experience Chicago at the Holidays
stevetD8739SF, Dec 2025
Well-run tour that our kid enjoyed! Comfortable pace that shows so much!
Highly recommended! We brought our 4 year old along expecting to abandon after 30 minutes or so, but the boy loved the full 2 hours. Perfect mix of indoor/outdoor with a bathroom break. Scott was fantastic as guide. I’ve been to Chicago this time of year a dozen times, and learned/saw MANY new things - wish I had done this way sooner! There were 20 total in the group (5 in our family), and everyone was so nice! I would do this again!!!
Read more
Illinois Tours
Attractions
Guides
Calendar
View more
View more