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Chicago and Milwaukee Getaway by Train

5 Nights from $910*
* Sample price: priced within the past 7 days for a 5/17/2026 arrival, departing Miami MIA (FL), US. Choose departure city, cabin and dates.

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This 5 night sample itinerary includes:

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

So let's bask in the glow of Illinois and Wisconsin best cities!. An adventurous train ride from Chicago (The wind city will blow you away with its steely skyscrapers, museums and rocking festivals) and Milwaukee (with its acclaimed breweries, the Major League Brewers, and birthplace of the esteemed American motorcycle manufacturer, Harley-Davidson).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
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