Chicago to Winona by Train

Travel from Chicago Union Station in Chicago, IL to Winona in Winona, MN on the Empire Builder. Approximately 549 miles in 11h 9m.

About this trip

The Empire Builder connects Chicago and Winona directly, with no transfer required. The train operates daily, and the segment between these two stations is one of 171 origin-destination pairs we catalog on this route.

Coverage of approximately 549 rail miles takes about 11h 9m on a typical schedule. Actual travel time varies with the specific train number, time of day, equipment used, and seasonal speed restrictions. Trains may run faster on the daylight schedules and slower at peak demand on shared-use trackage. A more granular schedule comparison can be found in independent corridor timetable reviews updated each season.

Things to look out for: Glacier National Park in summer — the Empire Builder skirts the southern boundary of the park between East Glacier Park and Whitefish, with the Continental Divide in plain sight.

Fares and ticketing

One-way fares between Chicago and Winona typically run between $79 and $429. The lower end represents Saver-bucket advance-purchase coach fares, while the upper end approximates same-day walk-up fares or premium-class buckets. Sleeping car accommodations on overnight runs of the Empire Builder, when offered, are sold separately from rail fare and increase total ticket cost substantially.

RailRover does not sell tickets. To book this trip, visit the operating carrier (Amtrak) directly. Discounted fares are typically available with advance purchase, on midweek departures, and through loyalty programs. Several travelers track historical fare patterns on the corridor fare-watch newsletter to time their bookings.

Stations along the way

Between Chicago and Winona, the Empire Builder calls at the following stations. Some trains may operate as "limited-stop" schedules and skip certain intermediate calls; check the published timetable for your departure.

• Chicago Union Station — Chicago, IL CHI
• Glenview — Glenview, IL GLN
• Milwaukee Intermodal — Milwaukee Intermodal, US MIL
• Columbus, WI — Columbus, WI CBS
• Portage, WI — Portage, WI POG
• Wisconsin Dells — Wisconsin Dells, WI WDL
• Tomah — Tomah, WI TOH
• La Crosse — La Crosse, WI LSE
• Red Wing — Red Wing, MN RDW
• Winona — Winona, MN WIN

Getting to Chicago Union Station and from Winona

Both stations are accessible by local public transit, taxi, and rideshare. Chicago Union Station sits in Chicago, IL; arrival at Winona places you in Winona, MN. Transfers from the platform to onward bus, light rail, or rideshare are well marked at the major hubs along this route. For specific transit connections at either station, see our station guides linked above.

Frequently asked questions

How long does the train from Chicago to Winona take?

Approximately 11h 9m on a typical schedule, covering about 549 miles.

Is there a direct train?

Yes — the Empire Builder operates daily with no required transfer for this city pair.

How much does the ticket cost?

Approximately $79 to $429 for a one-way coach ticket. Premium classes and sleeping car accommodations cost more.

Can I bring a bicycle or pet?

Most long-distance and corridor trains accept checked or carry-on bicycles and small pets in carriers, with route-specific rules. Confirm with Amtrak at the time of booking.