Just outside Chicago, this thoughtfully planned road trip takes you from lakeside scenery and charming small towns to playful animal encounters and a unique museum experience. With a mix of relaxing and lighthearted stops, it’s an easy and ...
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Fun but not the best for winter
There were some really cool locations here! However, one was closed for the season which was disappointing, and I checked the travel notices the morning of. I would recommend taking this trip in fall, spring, or summer. Not the winter like we did. But we at least know some spots we can go back to later!
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Sarah · February 11, 2025
Fun day!
We were very excited to go on our day date full of surprises and we were not disappointed. The only thing I would change is the time of year we went. We missed the fall colors but that is on us not Guess Where trips. This was such a great day and we went places we never knew existed and we made lots of friends and wonderful fun memories. I have many pictures but I only shared the ones that wouldn't spoil the surprise. Will definitely do this again!
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Christy · November 19, 2024
My First Guess Where Trip
Loved the places! Truely charming as described! I lived not far from these places for 7 years and didn't know about these things nearly in my own back yard. :)