
Chicago Tours in Fall
Planning for a trip to Chicago during Fall? We offer 20+ tour packages to Chicago departing in Fall that have 100+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Chicago on your Fall holiday.
We guarantee the best prices on all our tours. If you find a lower price within 24 hours of booking, we'll match it.
Note: Prices may vary based on availability and demand.
10 Best Fall Tours in Chicago
Join one of these handpicked Chicago Fall tour packages, tailored to the season.
See all Chicago Fall Tours
Top Chicago Tour Activities for Fall
From city sightseeing tours to cultural, religious and historic sites and others, here are some popular tour activities in Chicago with departures in Fall.
10 Best Chicago December Deals
December Deals exclusive deals on Chicago Fall tours — limited-time massive savings on premium travel packages!
See all Chicago Fall travel deals
Reviews of our Chicago Tours for Fall
Feedback from guests whose tour started in/around Chicago during Fall.
I absolutely love Chicago!! The tour we had was great! I was there in 2024 but I was able to experience other areas and hear the local stories. All of the tours were incredible! I enjoyed all of them. Not as impressed with Bronner’s but glad I experienced it and bought souvenirs. I enjoyed Mackinac Island. Very unique experience. The grand hotel was lovely. Probably my favorite tour was the Ford Co Rouge. So fascinating to watch the assembly of the trucks. I could have watched for hours!! Jamie, our tour guide was wonderful. So helpful, knowledgeable and friendly but also kept us on track! Loved the way he handled the bus seating! I enjoyed our group meals and really had a great time. Joe, our driver was very nice, too!! This was my first vacation with a tour group like this. It was definitely an adjustment needing to follow strict leave times lol
Definitely Mackinac Island was the highlight and I wish we had more time there. The history lectures were FANTASTIC and the building was so interesting. Be sure to browse other rooms because they are all different and so colorful!
Chicago was amazing. AbeYtif city. Wish there had been more time. I really wanted to go to the art museum. Also loved frankenmuth and Bronner’s xmas store. Another highlight was the Henry Ford museum
Mackinac Island was wonderful, of course, but I also enjoyed Frederik Meijer Gardens & Sculpture Park very much. The sculpture garden tour was excellent but wish we could have had more time there to explore the sculpture garden on our own.
We thoroughly enjoyed our Mackinaw Island trip with Tour Director Michael Hepler! He was friendly, organized, knowledgeable and caring! He took care of every detail to make sure our trip was a memorable experience. We hope to see him again on a future trip!
Our Tour Manager was excellent! He was very informative and organized throughout the tour! We had a great variety of things to visit and experience. Staying at the Grand Hotel was certainly a highlight!
Get a customized trip to Chicago in Fall
Plan a multi-country or regional adventure across Chicago in Fall, with help from a local expert.


















