
Chicago Tours in October 2026
Planning for a trip to Chicago during October? We offer 20+ tour packages to Chicago departing in October 2026 that have 90+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Chicago on your October holiday.
See all Chicago October 2026 Tours
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 October 2026 Tours in Chicago
Join one of these handpicked Chicago October 2026 tour packages, tailored to the season.
See all Chicago October 2026 Tours
Chicago October 2026 Tour Types
Discover Chicago October 2026 tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
Reviews of our Chicago Tours for October
Feedback from guests whose tour started in/around Chicago during October.
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 October 2026
Plan a multi-country or regional adventure across Chicago in October 2026, with help from a local expert.













