Route 66 Neighborhoods by Trolley
Media Attention
Click the picture to see NBC5 riding on my Route 66 Neighborhoods tour
Click the picture to read about the launch of the Route 66 Neighborhoods tours
Click the picture to read a Chicago Magazine feature on the Route 66 Neighborhoods tour
Click the picture to read a City Cast Chicago feature on the Route 66 Neighborhoods tour
Click the picture to read all about the Route 66 Neighborhoods tour on Rollingout
Click the picture to read all about the Route 66 Neighborhoods tour on American Roads and Global Highways
Click the picture to read Choose Chicago announcing the launch of the Route 66 Neighborhoods tour
Tour Description
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 neighborhoods?
All of these aforementioned topics and so much more are explored on this fun trolley tour! Since we are celebrating Route 66’s 100th birthday in 2026, it is the perfect was to discover Chicago’s portion of this famous highway. This one-of-a-kind tour is available as a public tour where you can get individual tickets in 2026 or anytime as a private tour for your group.
I hope to see you on this special tour celebrating Chicago’s portion of the country’s most iconic road!
Tour Details
Start Time
10:00am on select dates in 2026 (this tour is also available anytime as a private tour for your group)
Duration
2.5 hours
Starting/Ending Location
The tour starts and ends in the eastern bus loading area for the Art Institute of Chicago's Modern Wing at 230 S Columbus Drive.
Parking
If you need nearby parking for your car, you can get a discounted rate by ordering in advance here. The closest of the four garages listed on that site is the Millennium Park garage.
Walking Distance
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.
Accessibility
All of the trolleys are wheelchair-accessible.
Price
$50 per person (the free tours from prior years funded by grant are unfortunately no longer available)
What is Included
Everyone will receive a one-of-a-kind trolley tour.
What to Bring
If you bring a mobile device, you will have access to a hidden webpage referenced throughout the tour that includes historical photos, sites to check out, and more.
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Among Tripadivsor's top 10% of reviewed experiences
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Runner-up for the Chicago Reader's Best Tour of 2021, 2022, and 2023
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Watch Mike’s discuss some of his unique tours on WGN TV
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WTTW’s Geoffrey Baer: “He is a tour guide’s tour guide.”
Frequently Asked Questions
Who is the tour guide?
Mike McMains creates and delivers all Tours With Mike experiences, so you know you are getting a professional, passionate guide.
How do I find Mike?
He will be at the aforementioned starting point wearing a Tours With Mike polo, hat, or some other type of branded attire or accessory.
Do we go inside buildings?
You can choose to go inside of Lulu’s Hot Dogs midway through the tour to visit the restroom and/or pick up food/drink to go.
Are dogs allowed on the tour?
Dogs are not allowed on the trolley.
Is there a restroom stop on the tour route?
If you need a restroom before the tour begins, the closest one is just to the north in Millennium Park next to Millennium Hall (11 N Michigan Ave). There is another restroom opportunity midway through the tour in Lulu’s Hot Dogs.
Can I get my ticket in-person immediately before the start of the tour?
Tickets need to be reserved through this website in advance, because capacity is limited.
What is the cancellation/refund policy?
If you give Tours With Mike at least one week notice of your cancellation, you can get a full refund on your ticket.
What if it is raining?
The tour almost entirely takes place in sheltered areas, so your exposure to rain is very limited.
Can I book this as a private tour?
If you would like a private version of this tour, please fill out the form below to contact Mike.