phone_icon

Destinations

❮Main Menu

My Booking

❮Main Menu

About Us

❮Main Menu
USA

Chicago and Milwaukee Getaway by Train

5 Nights from $665*
* 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.

Customize and Book

Add Outbound & Return Flights

This 5 night sample itinerary price 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).

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

USA

Customer Reviews

Customer Reviews

  • You can now

    Stagger

    your payment!