Windy City Express


Friends of the 261 offers you the opportunity to ride vintage passenger cars from the Twin Cities to Milwaukee or Chicago behind Amtrak’s Empire Builder*. 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.

Ride 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 get away, current rates for Spirit is offering tickets starting at $43 one way.*

Watch nature along the Mississippi River as you pass through Red Wing and Winona. Look for bald eagles as you ride atop the Super Dome. Built in 1953, today, its comfortable seating and lounge area make it a classic, with views that can only be matched by few rail cars running today.

This trip 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.

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

Chicago to Minneapolis/St Paul
Depart Chicago Union Station – 2:15 pm
Depart Milwaukee Amtrak Station – 3:52 pm
Arrive St Paul Union Depot – 10:03 pm

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