
Chicago City sightseeing Trips
City sightseeing trips in Chicago. Looking to explore Chicago on a city sightseeing tour? We offer 10+ city sightseeing tours through-out Chicago, backed by 90+ reviews and offering discounts up to 40%. All our trips are offered by expert trip designers and Chicago destination experts, with trip durations ranging from 7 to 23 days.
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10 Best City sightseeing Tours in Chicago
Discover our best City sightseeing tours in Chicago, based on reviews and times booked.
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Chicago City sightseeing Tours for all Age Groups
Find tours designed for every age group, from young adventurers to senior travelers. Travel with like-minded explorers and enjoy experiences tailored to your needs.
Chicago City sightseeing Tour Types
Discover Chicago City sightseeing tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
Chicago City sightseeing Tour Reviews
Guest reviews from travelers on City sightseeing tours in and around Chicago
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!
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