Hop on the trolley and travel through Chicago's Route 66 history

Chicago isn’t just a world-class destination, it’s the starting line of America’s most legendary highway. Now, a charming trolley tour is inviting locals and visitors alike to rediscover the Windy City’s place in history through the Route 66 Neighborhoods Tour by Tours With Mike.

With Route 66 celebrating its 100th anniversary in 2026, this immersive experience arrives at the perfect moment to explore the stories, culture and quirky landmarks that launched the “Mother Road.”

Where the Mother Road Begins

When people picture Route 66, they often imagine desert highways and roadside diners. But every legendary journey has a beginning, and for Route 66, that beginning is Chicago.

The Route 66 Neighborhoods by Trolley tour dives deep into the road’s Chicago roots, exploring the communities, small businesses, and pop-culture connections that grew along the historic highway. Guests learn how Route 66 influenced music, television, film, literature, and the development of neighborhoods across the city. 

This isn’t just a sightseeing trip, it’s a rolling history lesson filled with storytelling, nostalgia, and hidden gems.

What to Expect on the Tour

The experience begins and ends at the eastern bus loading area of the Art Institute of Chicago’s Modern Wing at 230 S. Columbus Drive. From there, guests hop aboard a vintage-style trolley for a relaxed, 2.5-hour journey through Chicago’s Route 66 legacy. 

Tour highlights include:

• Fascinating history of Route 66’s Chicago origins

• Stories of roadside attractions and neighborhood development

• Pop-culture connections to the famous highway

• Access to a special mobile webpage with historical photos and bonus content during the tour 
  

Midway through the experience, guests can step off the trolley to see a vibrant Route 66 mural, grab a snack, or visit Lulu’s Hot Dogs before continuing the journey. 

Meet the Guide Behind the Journey

The tour is created and led by Chicago guide Mike McMains, whose storytelling and passion have earned major media attention and accolades. The tour has landed among TripAdvisor’s top 10% of reviewed experiences and was runner-up for Chicago Reader’s Best Tour multiple years. 

In short: you’re in expert hands.

Tour Details at a Glance

Season: Select dates May–November 2026

Start time: 10:30 a.m.

Duration: 2.5 hours

Price: $50 per person

Accessibility: Wheelchair-accessible trolley (advance notice recommended) 

Public tours run throughout the season, and private tours are available for groups year-round. 

Tickets must be reserved in advance due to limited capacity.

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Why This Tour Is Perfect Right Now

With Route 66 turning 100 in 2026, interest in the historic highway is surging nationwide. This trolley tour offers Chicagoans and visitors a unique way to celebrate the centennial without leaving the city. It’s nostalgic, educational, fun and delightfully easy. No road trip required.

Plan Your Ride

Tickets and tour dates are available here: Book the Route 66 Neighborhoods Tour. Whether you’re a lifelong Chicagoan or a curious traveler, this trolley adventure proves that sometimes the best road trip starts right in your own backyard.