Train from Winona, MN to Chicago: Tickets & Schedules

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Next train departures

Next departures for Winona to Chicago on October 12
Operated byVehicle typeDeparture timeDeparture locationTrip durationArrival timeArrival locationRecommendedPrice and booking link
AmtrakTrain
  • Wifi
  • Toilet
  • Power outlets
Winona Station
Chicago (Union Station), ILCheapest
AmtrakTrain
  • Wifi
  • Toilet
  • Power outlets
Winona Station
Chicago (Union Station), ILFastest
AmtrakTrain
  • Wifi
  • Toilet
  • Power outlets
Winona Station
Chicago (Union Station), ILNo tags
AmtrakTrain
  • Wifi
  • Toilet
  • Power outlets
Winona Station
Chicago (Union Station), ILNo tags

Last refresh of the prices: Yesterday at 11:21 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 50 minutes and with fares starting at just RUB 3,365, it presents an excellent value for a comfortable ride.

3train per day
5h 50mAverage Duration
251 milesDistance
37kgCO₂ emissions
Bus
Average PriceRUB 16,064 - RUB 16,064Average Duration15h 45m
10kg CO₂e
Train
Average PriceRUB 3,365 - RUB 58,125Average Duration5h 50m
37kg CO₂e

Frequently asked questions about traveling 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 from RUB 3,365. The average price for this train route is around RUB 6,171. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.

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

    The average train ride duration from Winona to Chicago is 5h 50m, covering a distance of 251 miles (405 km). The quickest train can get you there in 5h 40m and is operated by Amtrak.

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

    Several major train operators operate on this route with 3 trains available per day.

  4. What is the earliest and latest departure time for the train from Winona to Chicago?

    The earliest train departs from Winona to Chicago at 11:01am. And 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
10/09
RUB 54,133
10/10
RUB 3,149
Today
RUB 5,860
10/12
RUB 9,008
10/13
RUB 3,149
10/14
RUB 11,194
10/15
RUB 17,403
10/16
RUB 7,346
busbud logoThe cheapest trip from Winona, MN to Chicago was searched and found on Oct 10, 2026 with a price of RUB 3,149

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 RUB 3,149 to RUB 54,133 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 RUB 3,149 which is on 2026-10-13.

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 RUB 6,171 on average. If you're on a budget, you'll find cheap tickets from RUB 3,365. 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 50m - that's the fastest way to get there!

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