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Transportation Tours

Best results for Transportation Tours in Chicago, IL

Showing 1-3 of 3 results

2-Hour Chicago Prohibition Gangster Bus Tour

Bus Van and Limo Tours

2-Hour Chicago Prohibition Gangster Bus Tour

Ride Chicago’s 1920s–30s gangster trail with actor guides

Ride Chicago’s 1920s–30s gangster trail with actor guides

4.6 • 371 reviews

$54/ person

Ride a Lamborghini Urus on a 10-Mile Chicago Tour

Bus Van and Limo Tours

Ride a Lamborghini Urus on a 10-Mile Chicago Tour

Cruise Chicago on a 10-mile Lamborghini Urus ride

Cruise Chicago on a 10-mile Lamborghini Urus ride

4.2 • 228 reviews

$89/ person

Chicago Rolls-Royce City Tour

Bus Van and Limo Tours

Chicago Rolls-Royce City Tour

See Chicago landmarks from the back seat of a Rolls-Royce with a private driver

See Chicago landmarks from the back seat of a Rolls-Royce with a private driver

4.2 • 228 reviews

$207/ person

Travel guides for Transportation Tours

12 Best Heritage Train Rides in America for Your Travel Bucket List

Field Guide • 2026

12 Best Heritage Train Rides in America for Your Travel Bucket List

One line bends through 381 curves in 40 miles; another climbs to 11,000 feet. Here's what each railway actually preserves, and when to ride it.