Windy City 2019

October 19 & 20, 2019



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 One way October 19 or 20, 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 Silver Palace. Built in 1948, 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!

October 19th will feature premier rolling stock, such as:  Wisconsin Valley, Super Dome #53 & Cedar Rapids

October 20th will feature premier rolling stock, such as: Lake Pepin, Fox River Valley, & Silver Palace

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


October 19th & 20, 2019
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

Arriving/Parking St Paul Union Depot

*Due to Amtrak’s new private car policy, we are restricted due to Amtrak’s on-time performance and can not guarantee the train will run as scheduled.

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