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Milwaukee and Chicago Getaway by Train

5 to 7+ Nights from $316*
* This sample price: priced within the past 7 days for check-in on 2/28/2025. Choose your own arrival dates.

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This 5 night sample itinerary includes:

  • 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). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

Flexible Itinerary

  • Milwaukee, WI

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  • Chicago, IL

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USA

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Trip Summary

  • Milwaukee, WI
    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, 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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