Trains tickets from Chicago to Winona (MN)

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TodayJun 17
TomorrowJun 18
from $47
ThuJun 19
from $108
FriJun 20
from $108
SatJun 21
from $108
SunJun 22
from $450
MonJun 23
from $156
TueJun 24
from $108

Trains leaving tomorrow

One passenger / one way

  • This trip is recommended because it is: Cheapest
    Departure time: June 18 at
    Departure city: Chicago
    Departure location: Chicago (Union Station), IL
    Arrival time: June 18 at
    Destination city: Winona
    Destination location: Winona Station
    Operated by: AmtrakAmtrak
    Vehicle: TrainDuration:
  • This trip is recommended because it is: Fastest
    Departure time: June 18 at
    Departure city: Chicago
    Departure location: Chicago (Union Station), IL
    Arrival time: June 18 at
    Destination city: Winona
    Destination location: Winona Station
    Operated by: AmtrakAmtrak
    Vehicle: TrainDuration:
  • Departure time: June 18 at
    Departure city: Chicago
    Departure location: Chicago (Union Station), IL
    Arrival time: June 18 at
    Destination city: Winona
    Destination location: Winona Station
    Operated by: AmtrakAmtrak
    Vehicle: TrainDuration:
  • Departure time: June 18 at
    Departure city: Chicago
    Departure location: Chicago (Union Station), IL
    Arrival time: June 18 at
    Destination city: Winona
    Destination location: Winona Station
    Operated by: AmtrakAmtrak
    Vehicle: TrainDuration:
  • Departure time: June 18 at
    Departure city: Chicago
    Departure location: Chicago (Union Station), IL
    Arrival time: June 18 at
    Destination city: Winona
    Destination location: Winona Station
    Operated by: AmtrakAmtrak
    Vehicle: TrainDuration:

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Train Chicago to Winona: Trip Overview

Please note, this information is subject to change.

Average ticket price$108
Average train trip duration5h 35m
Number of daily trains3
Earliest train departure6:10am
Distance252 miles (405 km)
Latest train departure3:05pm

Chicago to Winona Train

With Busbud, comparing and booking tickets for a train from Chicago to Winona is a breeze. Browse through an extensive selection of train fares and train schedules to find the best deals.

We make it our job to connect you with the most dependable companies that offer train service from Chicago to Winona.

Whether it is train tickets or first class train tickets going to Winona from Chicago, we help you find what you're looking for based on how much of a budget you have.

Frequently asked questions for your trip Chicago - Winona (MN)

Find cheapest prices for trains

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

Best price found
06/15
$128
06/16
$103
Today
$36
06/18
$44
06/19
$103
06/20
$103
06/21
$103
06/22
$433
busbud logoThe cheapest trip from Chicago to Winona was searched and found on Jun 17, 2025 with a price of $36

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

You can expect to pay from $36 to $634 for a train ticket from Chicago to Winona based on the last 2 days. You can expect to find the cheapest price for the trip at $44 which is on 2025-06-18.

About Train Travel

Train Travel Tips

Taking the fastest trains allows you to travel at speeds greater than 300 km/h. Taking a trip from Chicago to Winona is not only much quicker but more comfortable too! You can usually travel directly to the city centre and save time while you're at it.

Whether you take a regional or high-speed train to Winona, you’ll help reduce the environmental impact and carbon footprint of your trip. As you watch the landscapes unfold before your eyes, you can tell yourself that with this choice, you are making sure they remain protected.

By choosing the train between Chicago and Winona, you emit up to 30 times less CO2 than for the same journey made by plane or car!

Tune out to the fine sounds of your best music playlist on your train trip from Chicago to Winona while indulging in miles on end of beautiful scenic views.

Did you know?

Railway companies played a major role as early as 1883 in the use of time zones as we know them today.

You can find the straightest railway in the world in Australia. This railway line is 478 kilometres long and is also considered the longest and straightest railway line in the world.

The first high-speed train line was inaugurated in 1964, in Japan, to connect Tokyo with Osaka. It was during the Olympics that the first passengers traveled aboard the Shinkansen at a speed of 210 km / h.

Will you be returning to Chicago by train?

Train from Winona to Chicago

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