Windy City Express
October 6-8, 2023
Buy Tickets Online!

Friends of the 261 are offering you an 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. Both trips are round trip, if you chose you may also ride one-way. With affordable air fares around the country, finding away home has never been easier.

Both trips will be featuring Friends of the 261 equipment, Caritas and Super Dome, these 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


October 6, 2023

Minneapolis/St Paul to Chicago

Depart St. Paul Union Depot – 8:50 am
Arrive Milwaukee Amtrak Station – 2:57 pm
Arrive Chicago Union Station – 4:45 pm

October 8, 2023

Chicago to Minneapolis/St Paul

Depart Chicago Union Station – 3:05 pm
Depart Milwaukee Amtrak Station – 4:45 pm
Arrive St. Paul Union Depot – 10:56 pm

Both Trips are one-way from Minneapolis/St. Paul to Chicago.

Food is included in the ticket price.

*Terms & Conditions Apply, This is NOT an excursion with the steam engine Milwaukee #261 or diesel Milw #32A