
Chicago Tours in June 2026
Planning for a trip to Chicago during June? We offer 20+ tour packages to Chicago departing in June 2026 that have 90+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Chicago on your June holiday.
See all Chicago June 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 June 2026 Tours in Chicago
Join one of these handpicked Chicago June 2026 tour packages, tailored to the season.
See all Chicago June 2026 Tours
Chicago June 2026 Tour Types
Discover Chicago June 2026 tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
Reviews of our Chicago Tours for June
Feedback from guests whose tour started in/around Chicago during June.
This was a wonderful tour, our second tour with Collette (we also did Islands of New England in October 2024, which we thoroughly enjoyed). My husband is a native of Michigan and we have previously visited most of the places on the tour, including Chicago and Mackinac Island, but we had never stayed in the Grand Hotel or visited Holland, MI. We were eager to see the Tulip Festival and learn more about it. We enjoyed visiting the museums in Chicago again, and in fact, went a day early to have more time to visit them (but this plan was unfortunately foiled by a canceled plane flight, causing us to arrive the next day). For me, the highlights were visiting the Art Institute of Chicago again and staying at the luxurious Grand Hotel. And oh my--- the food at the Grand Hotel!! To die for!! But the REAL highlight of our trip was our tour manager, Don Littlefield!!!!! I cannot say enough about what an excellent tour manager he was! Very well-organized. always providing us with a detailed daily schedule as well as detailed extra information about the cities we were visiting, good nearby restaurants, nearby drugstores, and even as QR code to scan to get the complete schedule on your cell phone! and all the "extras" were very much appreciated-- air fresheners, cookies, etc. And to top it off, the surprise video he made from photos of our trip!!! Don is truly THE BEST tour manager my husband and I have encountered. The icing on the cake is that he was very approachable, funny, and obviously truly loved making sure his traveling guests were having the best possible experience. We would follow him ANYWHERE on a tour!!!
Being on Mackinac Island was a bit like stepping back in time. The entire tour was good (my first tour but not my last!). We especially enjoyed being in Chicago. The weather was quite cool with sunny skies, but they had prepared us to dress in layers. We had a bus tour of the city with a local guide, David, who used no notes and spoke well with knowledge (gathered from living there his entire life) and humor. All five high school friends in our 70s would love to go back!
For an organized tour with a busload of people, Collette did an outstanding job! The tour manager was always on top of things, and I could count on everything being done as expected - for example, never had to worry about where my luggage was. We did the tour because of where it went, and we were not disappointed. Would definitely do it again!
Loved Chicago the city is amazing. could have spent lire time there. Holland nice & festival was pretty. Macon island would have liked more time to explore the national park there more. The Grand Hotel was grand would have liked to get more oral history from a dissent there. The Bavarian Inn was nice but not a day long event. Loved Alden Dows house tour could have spent more time there as well as Tge Henry Ford museum. Great trip, lovely people and would derail memories.
Loved Henry Ford Museum, Fred Meyer Sculpture Garden & Museum, Aldon Low House, Chicago, Bay City Hotel & Meal! Disappointed in Mackinac Island due to flies, overpriced items, etc.
Get a customized trip to Chicago in June 2026
Plan a multi-country or regional adventure across Chicago in June 2026, with help from a local expert.













