Windy City Express

Friends of the 261 are offering you the opportunity to ride our vintage passenger cars from the Twin Cities to Milwaukee or Chicago. This trip will be on the route of behind Amtrak’s Empire Builder* along the Mississippi River. Watch nature along the Mississippi River as you pass through Red Wing and Winona. Look for bald eagles as we pass through Lake Pepin on our way through central Wisconsin.

Our fully restored passenger cars offer a memorable journey you’ll cherish for years to come! Meticulously refurbished, these cars recall the era when traveling was half the vacation. This trip is a one-way journey from Minneapolis/St. Paul to Milwaukee or Chicago. With affordable air fares around the country, finding away home has never been easier. For an affordable weekend getaway, currently for Spirit is offering tickets starting at $43 one way.*

Both trips will be featuring Friends of the 261 equipment, the cars will start our journey by returning to the route the Milwaukee Road once traveled in regular service. These meticulously refurbished, fully restored cars recall the era when traveling was half the fun and offer a memorable journey, you’ll cherish for years to come!

While riding the rails, enjoy freshly-prepared meals and libations knowing that you are supporting the restoration of the Milwaukee Road Steam Locomotive 261.

These trips will have limited seating, all in premium class. With the recent reduction in air fares between the Twin Cities and Chicago, you may wish to fly one way and take the train the other.

We look forward to see you next year on the Windy City Express. If you missed this years Windy City Express, sign up for our email list and we will let you know when tickets go on sale for the next Windy City!

Windy City – Twin Cities to Milwaukee & Chicago


Minneapolis/St Paul to Chicago
Depart St. Paul Union Depot – 8:00 am
Arrive Milwaukee Amtrak Station – 2:07 pm
Arrive Chicago Union Station – 3:55 pm

  • Both Trips are one-way from Minneapolis/St. Paul to Chicago.
  • Food is included in the ticket price.

*Terms & Conditions Apply, These trips are one way from Minneapolis/St Paul to Chicago only. This is NOT an excursion with the steam engine Milwaukee 261 or diesel Milw 32A