DISCOVER THE ULTIMATE AMERICAN ROAD TRIP

Roaring Twenties <strong>Chicago</strong>

Roaring Twenties Chicago

Illinois - Illinois

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  • 14 stops
  • 300 miles
  • 3 days

Take a Lindy Hop back in time on our Roaring Twenties road trip of Chicago’s most iconic sights. Experience the razzle dazzle of the historic theater, trace the footsteps of bootleggers and try plenty of deep-dish pizza along the way.
Hit the open road and explore Starved Rock State Park, before returning to Downtown to enjoy your new-found freedom at one of the city’s coolest jazz clubs.
Neon lights, Ferris wheels and all-American diners – enjoy all this and more on your Chicago road trip.

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