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Milwaukee and Chicago Getaway by Train

5 Nights from $685*

* Sample price: priced within the past 7 days for a 1/8/2027 arrival, departing Miami MIA (FL), US. Choose departure city, cabin and dates.

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This 5 night sample itinerary price includes:

Flight into Milwaukee and out of Chicago
Hotel for 2 nights in Milwaukee
Train from Milwaukee to Chicago
Hotel for 3 nights in Chicago

Let us appreciate the excellence of the top cities in Illinois and Wisconsin!. Embark on an exciting train journey from Milwaukee (with its acclaimed breweries, the Major League Brewers, and birthplace of the esteemed American motorcycle manufacturer, Harley-Davidson) to Chicago (The wind city will blow you away with its steely skyscrapers, museums and rocking festivals).

Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.

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Hot dogs, Hollywood, Historical Personalities, Baseball, Mount Rushmore, The Grand Canyon, American Football, and the Golden Gate Bridge are just a few of the iconic landmarks, foods, and sports that the United States of American is known for. The USA is the most dominant economic and military powerhouse in the entire world, the most famous country in the world. The US is known for its sports, good culture, music, movies, technological innovations, and historical personalities. From the glitz and glam of Hollywood filled with movie stars and celebrities to the stunning coastlines of the Gulf of Mexico and the wild shores of Maine, the US offers 50 states to visit boasting a variety of landscapes and stunning attractions.

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Milwaukee, WI

Milwaukee is the largest city in Wisconsin, making it a regional hub for everything from culture to commerce. Milwaukee is a place where 19th-century historic buildings share the same city blocks as 21st-century urban renewal projects. It is one of the beer capitals of the world, and at one time was home to the world`s four largest breweries. Today Milwaukee is famous for beer as well as its budding culinary scene, popular cultural events, and plentiful boating and water sporting activities due to its location on Lake Michigan.

Explore the Milwaukee Art Museum, Harley-Davidson Museum, Mitchell Park, Discovery World, Milwaukee Public Museum, Milwaukee County Zoo, Frederick Pabst Mansion, Milwaukee RiverWalk, Grohmann Museum, Cathedral Square Park, Lakeshore State Park, Milwaukee City Hall, Bronze Fonz, Charles Allis Art Museum, and so much more!

Chicago, IL

Chicago, on Lake Michigan in Illinois, is among the largest cities in the U.S. Famed for its bold architecture, it has a skyline punctuated by skyscrapers such as the iconic John Hancock Center, 1,451-ft. Willis Tower (formerly the Sears Tower) and the neo-Gothic Tribune Tower. The city is also renowned for its museums, including the Art Institute of Chicago with its noted Impressionist and Post-Impressionist works.

Explore the Millenium Park, Willis Tower, Navy Pier, Shedd Aquarium, Grant Park, Cloud Gate, Field Museum, Chicago Riverwalk and much more.

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Milwaukee and Chicago Getaway by Train

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This 5 night sample itinerary price includes:

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Milwaukee and Chicago Getaway by Train