How much is the train ticket from Chicago to Winona?

The cheapest train tickets from Chicago to Winona start from A$56. The average price for this train route is around A$125. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.

How long is the train journey from Chicago to Winona?

The average train ride duration from Chicago to Winona is 5h 50m, covering a distance of 251 miles (405 km). The quickest train can get you there in 5h 29m and is operated by Amtrak .

Which train operators service the Chicago to Winona route?

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

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

The earliest train departs from Chicago to Winona at 6:10am. And the latest train departs at 3:05pm.

Train Chicago to Winona from A$52 | Refundable Tickets

Next train departures

Next departures for Chicago to Winona on May 16
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended	Price and booking link
	Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	CheapestFastest
	Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	No tags

Next departures for Chicago to Winona on May 17
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:10am	Chicago (Union Station), IL	5h 50m	5:00pm	Winona Station	Cheapest
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	Fastest
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	No tags
Train	8:25am	Chicago (Union Station), IL	8h 35m	5:00pm	Winona Station	No tags

Next departures for Chicago to Winona on May 18
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:10am	Chicago (Union Station), IL	5h 50m	5:00pm	Winona Station	Cheapest
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	Fastest
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	No tags
Train	6:10am	Chicago (Union Station), IL	10h 50m	5:00pm	Winona Station	No tags
Train	8:25am	Chicago (Union Station), IL	8h 35m	5:00pm	Winona Station	No tags

Next departures for Chicago to Winona on May 19
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:10am	Chicago (Union Station), IL	5h 50m	5:00pm	Winona Station	Cheapest
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	Fastest
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	No tags
Train	6:10am	Chicago (Union Station), IL	10h 50m	5:00pm	Winona Station	No tags
Train	8:25am	Chicago (Union Station), IL	8h 35m	5:00pm	Winona Station	No tags

Next departures for Chicago to Winona on May 20
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:10am	Chicago (Union Station), IL	5h 50m	5:00pm	Winona Station	Cheapest
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	Fastest
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	No tags
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	No tags
Train	6:10am	Chicago (Union Station), IL	10h 50m	5:00pm	Winona Station	No tags

Next departures for Chicago to Winona on May 21
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:10am	Chicago (Union Station), IL	5h 50m	5:00pm	Winona Station	Cheapest
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	Fastest
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	No tags
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	No tags
Train	6:10am	Chicago (Union Station), IL	10h 50m	5:00pm	Winona Station	No tags

Next departures for Chicago to Winona on May 22
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:10am	Chicago (Union Station), IL	5h 50m	5:00pm	Winona Station	Cheapest
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	Fastest
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	No tags
Train	6:10am	Chicago (Union Station), IL	10h 50m	5:00pm	Winona Station	No tags
Train	8:25am	Chicago (Union Station), IL	8h 35m	5:00pm	Winona Station	No tags

Last refresh of the prices: Last Thursday at 8:07 PM CDT.

Compare 2 ways to go from Chicago to Winona

We recommend taking the train

Among the sustainable travel choices, the Train stands out as a good way to reach Winona. The journey takes about 5 hours 50 minutes and with fares starting at just A$56, it presents an excellent value for a comfortable ride.

3train per day

5h 50mAverage Duration

251 milesDistance

37kgCO₂ emissions

	Average Price	Average Duration	CO₂ emissions	Actions
Bus	Average PriceA$264 - A$273	Average Duration16h 45m	CO₂ emissions 10kg CO₂e
Train	Average PriceA$56 - A$231	Average Duration5h 50m	CO₂ emissions 37kg CO₂e

Train Companies

Amtrak

4.1/55,805 reviews

Staff4.7

Timeliness3.8

Cleanliness4.5

Wifi3.6

Based on 5805 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at A$56

US train companies:Amtrak, Amtrak Acela, Brightline

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

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

How much is the train ticket from Chicago to Winona?
The cheapest train tickets from Chicago to Winona start from A$56. The average price for this train route is around A$125. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the train journey from Chicago to Winona?
The average train ride duration from Chicago to Winona is 5h 50m, covering a distance of 251 miles (405 km). The quickest train can get you there in 5h 29m and is operated by Amtrak.
Which train operators service the Chicago to Winona route?
Several major train operators operate on this route with 3 trains available per day.
What is the earliest and latest departure time for the train from Chicago to Winona?
The earliest train departs from Chicago to Winona at 6:10am. And the latest train departs at 3:05pm.

Find cheapest prices for trains

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

Best price found

05/14

A$184

05/15

A$97

Today

A$119

05/17

A$184

05/18

A$184

05/19

A$119

05/20

A$148

05/21

A$184

The cheapest trip from Chicago to Winona, MN was searched and found on May 15, 2026 with a price of A$97

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, MN, as early as possible.

You can expect to pay from A$97 to A$866 for a train ticket from Chicago to Winona, MN based on the last 2 days. You can expect to find the cheapest price for the trip at A$119 which is on 2026-05-19.

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

The Train is the cheapest travel choice for this destination

Vehicle Type	Travel Time	Avg Price	Daily Departures
Vehicle TypeBus	Travel Time16h 45m	Avg PriceA$264	Daily Departures1
Vehicle TypeTrain	Travel Time5h 50m	Avg PriceA$125	Daily Departures3

The best way to travel between Chicago and Winona, MN is by train. By choosing the train, you'll get to save some money as you travel to your destination, as ticket prices cost A$125 on average. If you're on a budget, you'll find cheap tickets from A$56. If you're looking for the fastest way to get to Winona, MN, choose the train, as it will take you from Chicago to Winona, MN in about 5h 50m - that's the fastest way to get there!