GET YOUR KICKS ON ROUTE 66: CHICAGO
ABOUT
What comes to mind when you think of Route 66?
Do you think of the interesting attractions and small businesses that developed around it? What about its place in music, television, film, and literature? Is it the highway’s fascinating history or how it has shaped surrounding communities?All of these aforementioned topics and so much more are featured on this fun trolley tour!
Since we are celebrating Route 66’s 100th birthday in 2026, it is the perfect way to explore this famous highway’s starting portion in Chicago. Supplementing this experience, you will have access to webpage with historical photos and more that you can view on your own mobile devices.
Location:
The tour starts in the eastern bus loading area for the Art Institute of Chicago's Modern Wing at 230 S Columbus Drive.
Walking:
There is a stop midway through the tour where everyone can get off the trolley to see a wonderful Route 66 mural up close, visit the restroom, and/or grab some food/drink from Lulu’s Hot Dogs* to go.
*Purchases at Lulu’s is not included on the tour.
Duration
The tour portion is 2.5 hours. Add 1 - 1.5 for Lunch is immediately follows.
COST: includes lunch at Harry Caray’s Tavern on Navy Pier ( or comparable) a step on guide, special route 66 memorabilia and GTT snack bag.
$75 for groups of 20-30
$70 for groups of 31 plus
*Transportation is not included in the price quoted. Minimum of 20
This tour is being offered in partnership with Tours With Mike