How much is the train ticket from Winona to Chicago?

The cheapest train tickets from Winona to Chicago start at CLP 35,309. The average price for this train route is around CLP 72,362. Busbud recommends booking your tickets in advance to increase your chances of getting the lowest possible price.

How long is the train ride from Winona to Chicago?

The average train trip from Winona to Chicago takes 5h 55m and covers 405 km. The quickest train gets you there in 5h 34m and is operated by Amtrak .

Which train operators serve the Winona to Chicago route?

Several major train operators serve this route, with 4 trains available per day.

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.

Train Winona to Chicago from CLP 33,042 | Refundable Tickets

Next train departures

Next departures for Winona to Chicago on May 14
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:01am	Winona Station	8h 25m	7:26pm	Chicago (Union Station), IL	Cheapest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Fastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 25m	7:26pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 25m	7:26pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on May 15
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	1:31pm	Winona Station	5h 55m	7:26pm	Chicago (Union Station), IL	Cheapest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Fastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	1:31pm	Winona Station	7h 33m	9:04pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on May 16
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	1:31pm	Winona Station	5h 55m	7:26pm	Chicago (Union Station), IL	Cheapest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Fastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 25m	7:26pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 25m	7:26pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on May 17
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:01am	Winona Station	8h 25m	7:26pm	Chicago (Union Station), IL	Cheapest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Fastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	1:31pm	Winona Station	5h 55m	7:26pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 25m	7:26pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on May 18
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	1:31pm	Winona Station	5h 55m	7:26pm	Chicago (Union Station), IL	Cheapest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Fastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 25m	7:26pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 25m	7:26pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on May 19
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	1:31pm	Winona Station	5h 55m	7:26pm	Chicago (Union Station), IL	Cheapest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Fastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 25m	7:26pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 25m	7:26pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on May 20
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	1:31pm	Winona Station	5h 55m	7:26pm	Chicago (Union Station), IL	Cheapest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Fastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 25m	7:26pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 25m	7:26pm	Chicago (Union Station), IL	No tags

Last refresh of the prices: Yesterday at 6:38 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 55 minutes, and with fares starting at just CLP 35,309, it presents an excellent value for a comfortable ride.

4train per day

5h 55mAverage Duration

405 kmDistance

37kgCO₂ emissions

	Average Price	Average Duration	CO₂ emissions	Actions
Bus	Average PriceCLP 168,596 - CLP 168,596	Average Duration15h 45m	CO₂ emissions 10kg CO₂e
Train	Average PriceCLP 35,309 - CLP 288,950	Average Duration5h 55m	CO₂ emissions 37kg CO₂e

Train companies

Amtrak

4.1/55,801 reviews

Staff4.7

Timeliness3.8

Cleanliness4.5

Wi‑Fi3.6

Based on 5801 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the Wi‑Fi. Amtrak ticket prices on this trip start at CLP 35,309

US train companies:Amtrak, Amtrak Acela, Brightline

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.

How much is the train ticket from Winona to Chicago?
The cheapest train tickets from Winona to Chicago start at CLP 35,309. The average price for this train route is around CLP 72,362. Busbud recommends booking your tickets in advance to increase your chances of getting the lowest possible price.
How long is the train ride from Winona to Chicago?
The average train trip from Winona to Chicago takes 5h 55m and covers 405 km. The quickest train gets you there in 5h 34m and is operated by Amtrak.
Which train operators serve the Winona to Chicago route?
Several major train operators serve this route, with 4 trains available per day.
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

05-11

CLP 94,537

05-12

CLP 68,837

Today

CLP 94,537

05-14

CLP 99,126

05-15

CLP 117,482

05-16

CLP 33,042

05-17

CLP 61,495

05-18

CLP 61,495

The cheapest trip from Winona, MN to Chicago was searched and found on May 16, 2026 with a price of CLP 33,042

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 CLP 33,042 to CLP 568,135 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 CLP 33,042 which is on 2026-05-16.

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

The Train is the cheapest travel choice for this destination

Vehicle Type	Travel time	Avg Price	Daily Departures
Vehicle TypeBus	Travel time15h 45m	Avg PriceCLP 168,596	Daily Departures1
Vehicle TypeTrain	Travel time5h 55m	Avg PriceCLP 72,362	Daily Departures4

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 CLP 72,362 on average. If you're on a budget, you'll find cheap tickets from CLP 35,309. 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 55m —that's the fastest way to get there!