Route 66 Neighborhoods by Trolley
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, and you can experience it for FREE! Through sponsorship from Choose Chicago and the Illinois Department of Commerce & Economic Opportunity, you have 12 opportunities throughout Summer 2024 ride around the starting portions of Route 66 here in Chicago discovering interesting stories and sites. You will also get some complimentary treats!
Stops are included to explore the surrounding neighborhoods on your own for a bit and/or grab some lunch. The stops vary depending on the date:
You will have one longer stop in the vibrant Little Village neighborhood on the June 7, June 9, July 12, July 13, July 19, July 26, July 27, and August 9 tours.
There is a mini auto show with classic cars at two shorter stops along Route 66 on the July 20, July 21, August 10, and August 11 tours.
I hope you can join for this special tour celebrating Chicago’s portion of the country’s most iconic road!
Tour Details
Start Time
Please plan to arrive at 11:15 am so you can get checked in and do not miss the trolley tour starting at 11:30 am.
Duration
3.5 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 are one or two stops per tour where everyone exits the trolley. You can either spend the time off the trolley inside a restaurant and/or explore the neighborhood on your own a little bit.
Accessibility
The trolley is not wheelchair-accessible and requires a few steps to get in and out of it.
Price
Free (up to two tickets per registration)
What is Included
Everyone will receive a complimentary trolley tour, a bottle of water, and some treats. When attendees get off the trolley, they have time to grab lunch on their own.
What to Bring
If you bring a smartphone, you will have access to a webpage referenced throughout the tour that includes 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
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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 will go inside to pick up complimentary treats, and you can explore other sites in the neighborhood on your own.
Are dogs allowed on the tour?
Since the entire tour is on a trolley, dogs are not allowed.
Is there a restroom stop on the tour route?
If you need a restroom before the tour begins, there is one next to the starting location inside the Art Institute of Chicago. There is another restroom opportunity midway through the tour when we all get off the trolley.
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 can no longer attend, please fill out the form below to contact Mike ASAP to free up your spot for someone else.
What if it is raining?
The tour almost entirely takes place in sheltered areas, so your exposure to rain is very limited.
Are there any COVID-19 considerations in-place?
All tours follow guidelines laid out by the State of Illinois’s and City of Chicago’s health departments. Currently masks and proof of vaccination are not required. Your tour guide, Mike, has been fully vaccinated and boosted.
Can I book this as a private tour?
This tour is only offered 12 times throughout Summer 2024, but if you would like a private version of it, please fill out the form below to contact Mike.