Train from Winona, MN to Chicago: Tickets & Schedules

Next train departures

Next departures for Winona to Chicago on August 9
Operated byVehicle typeDeparture timeDeparture locationTrip durationArrival timeArrival locationRecommendedPrice and booking link
AmtrakTrain
Winona Station
Chicago (Union Station), ILCheapest
AmtrakTrain
Winona Station
Chicago (Union Station), ILFastest

Last refresh of the prices: Yesterday at 10:11 PM CDT.

Compare 2 ways to go from Winona to Chicago

We recommend taking the train

Among the sustainable travel choices, the Train stands out as a good way to reach Chicago. The journey takes about 5 hours 44 minutes, and with fares starting at just MAD 367, it presents an excellent value for a comfortable ride.

3train per day
5h 44mAverage Duration
405 kmDistance
37kgCO₂ emissions
Average PriceMAD 1,752 - MAD 1,752Average Duration15h 45m
10kg CO₂e
Average PriceMAD 367 - MAD 5,974Average Duration5h 44m
37kg CO₂e

Frequently asked questions about travelling from Winona, MN to Chicago by train

Please note that schedules, routes, or operator details shown here may be updated or vary at the time of your trip.

  1. How much is the train ticket from Winona to Chicago?

    The cheapest train tickets from Winona to Chicago start at MAD 367. The average price for this train route is around MAD 782. Busbud recommends booking your tickets in advance to increase your chances of getting the lowest possible price.

  2. How long is the train ride from Winona to Chicago?

    The average train trip from Winona to Chicago takes 5h 44m and covers 405 km. The quickest train gets you there in 5h 40m and is operated by Amtrak.

  3. Which train operators serve the Winona to Chicago route?

    Several major train operators serve this route, with 3 trains available per day.

  4. What are the earliest and latest departure times for the train from Winona to Chicago?

    The earliest train from Winona to Chicago departs at 11:01am. The latest train departs at 1:41pm.

Find cheapest prices for trains

Price is for a one-way ticket for one passenger and based on past searches.

Best price found
08-06
MAD 4,130
08-07
MAD 8,327
Today
MAD 983
08-09
MAD 1,422
08-10
MAD 640
08-11
MAD 983
08-12
MAD 983
08-13
MAD 1,269
busbud logoThe cheapest trip from Winona, MN to Chicago was searched and found on Aug 10, 2026 with a price of MAD 640

To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Winona, MN to Chicago, as early as possible.

You can expect to pay from MAD 640 to MAD 8,327 for a train ticket from Winona, MN to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at MAD 640 which is on 2026-08-10.

What's the cheapest way to go from Winona, MN to Chicago?

busbud logoThe Train is the cheapest travel choice for this destination

The best way to travel between Winona, MN and Chicago is by train. By choosing the train, you'll get to save some money as you travel to your destination, as ticket prices cost MAD 782 on average. If you're on a budget, you'll find cheap tickets from MAD 367. If you're looking for the fastest way to get to Chicago, choose the train, as it will take you from Winona, MN to Chicago in about 5h 44m —that's the fastest way to get there!

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