Chicago Multi-day Tours

Discover top multi-day tours from Chicago, including Midwest self-guided audio tours, Route 66 trips, Great Lakes adventures, and iconic US city tours.

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2 Day Private Tour Chicago to Mackinac Island Exploration

2 Day Private Tour Chicago to Mackinac Island Exploration

Leave the city's hustle behind and embrace the tranquility of Mackinac Island, a destination where cars are absent, and the charm of horse-drawn carriages preva

From $2,700.00 USD
5-Day Tour of Superior, Huron and Michigan from Chicago

5-Day Tour of Superior, Huron and Michigan from Chicago

Five days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are located in Lake Michigan in t

★ 5.0 (2)
From $1,348.00 USD
Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent Mil

★ 5.0 (2)
From $11.75 USD
Chicago Milwaukee and Lakes 6 Day Tour

Chicago Milwaukee and Lakes 6 Day Tour

Six days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are located in Lake Michigan in th

From $1,387.00 USD
Chicago to Washington D.C. Cherry Blossom 3-Day Tour

Chicago to Washington D.C. Cherry Blossom 3-Day Tour

Celebrate the beauty of spring and the rich history of the National Cherry Blossom Festival, commemorating the 1912 gift of 3,000 cherry trees from Tokyo to Was

From $496.00 USD
Continental US Train Zephyr Adventure CA -CO - Il

Continental US Train Zephyr Adventure CA -CO - Il

Embark on the adventure of a lifetime! Step aboard the iconic California-Chicago Train Expedition as we whisk you away on a journey that combines the thrill of

★ 3.5 (2)
From $5.00 USD
Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago

Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago

Take in three of the Great Lakes and a string of classic Midwest towns on this four-day small-group loop out of Chicago. Travel up the western shore of Lake Mic

★ 5.0 (2)
From $1,125.00 USD
Great Smoky Mountains,Gatlinburg 4-Day Tour from Chicago

Great Smoky Mountains,Gatlinburg 4-Day Tour from Chicago

1. Explore Motorsports Hall of Fame. 2. Be in the National Park with most visitors in US -- Great Smoky Mountains. 3. Southern dinner show Dixie Stampede feat

From $1,030.00 USD
Guided Audio Road Trip Route 66

Guided Audio Road Trip Route 66

Live the mythical Route 66 as it should be: at your own pace, with freedom and with the feeling of being walking a living history. This audio guide accompanies

★ 1.0 (1)
From $29.40 USD
Route 66 Multi Day Tour from Chicago to Los Angeles

Route 66 Multi Day Tour from Chicago to Los Angeles

Travel the legendary Route 66 in 14 unforgettable days - from Chicago to Los Angeles across eight states, discovering over 450 handpicked points of interest. Ex

From $10.00 USD
Routes POR Route 66 with Audio Guide

Routes POR Route 66 with Audio Guide

Route 66, known as "The Main Street of America", runs through eight states from Chicago to Santa Monica. EN route to Illinois, POR Missouri, Kansas, Oklahoma, T

From $56.44 USD
Small Group Bike Tours From Chicago to Lake Geneva

Small Group Bike Tours From Chicago to Lake Geneva

The route to Lake Geneva follows the incredible coastline of Lake Michigan and eventually into the rolling green hills of Wisconsin. Your group will stop to see

From $449.00 USD

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