Next train departures

Next departures for Winona to Chicago on July 25
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	1:41pm	Winona Station	5h 40m	7:21pm	Chicago (Union Station), IL	CheapestFastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags
Train	1:41pm	Winona Station	7h 23m	9:04pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on July 26
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended	Price and booking link
	Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Cheapest
	Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Fastest

Next departures for Winona to Chicago on July 27
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	1:41pm	Winona Station	5h 40m	7:21pm	Chicago (Union Station), IL	CheapestFastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags
Train	1:41pm	Winona Station	7h 23m	9:04pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on July 28
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	1:41pm	Winona Station	5h 40m	7:21pm	Chicago (Union Station), IL	CheapestFastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags
Train	1:41pm	Winona Station	7h 23m	9:04pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on July 29
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended	Price and booking link
	Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	CheapestFastest
	Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on July 30
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	1:41pm	Winona Station	5h 40m	7:21pm	Chicago (Union Station), IL	CheapestFastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags
Train	1:41pm	Winona Station	7h 23m	9:04pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on July 31
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	1:41pm	Winona Station	5h 40m	7:21pm	Chicago (Union Station), IL	CheapestFastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags
Train	1:41pm	Winona Station	7h 23m	9:04pm	Chicago (Union Station), IL	No tags

Last refresh of the prices: Yesterday at 11:04 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 COP 127,091, it presents an excellent value for a comfortable ride.

3train per day

5h 44mAverage Duration

251 milesDistance

37kgCO₂ emissions

	Average Price	Average Duration	CO₂ emissions	Actions
Bus	Average PriceCOP 606,844 - COP 606,844	Average Duration15h 45m	CO₂ emissions 10kg CO₂e
Train	Average PriceCOP 127,091 - COP 2,144,450	Average Duration5h 44m	CO₂ emissions 37kg CO₂e

Train Companies

Amtrak

4.1/55,845 reviews

Staff4.7

Timeliness3.8

Cleanliness4.5

Wifi3.6

Based on 5845 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 COP 127,091

US train companies:Amtrak, Amtrak Acela, Brightline

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.

How much is the train ticket from Winona to Chicago?
The cheapest train tickets from Winona to Chicago start from COP 127,091. The average price for this train route is around COP 291,215. 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 Winona to Chicago?
The average train ride duration from Winona to Chicago is 5h 44m, covering a distance of 251 miles (405 km). The quickest train can get you there in 5h 40m and is operated by Amtrak.
Which train operators service the Winona to Chicago 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 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

07/22

COP 274,201

07/23

COP 1,063,768

Today

COP 422,865

07/25

COP 274,201

07/26

COP 928,319

07/27

COP 340,274

07/28

COP 145,360

07/29

COP 422,865

The cheapest trip from Winona, MN to Chicago was searched and found on Jul 28, 2026 with a price of COP 145,360

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 COP 145,360 to COP 1,995,391 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 COP 145,360 which is on 2026-07-28.

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 PriceCOP 606,844	Daily Departures1
Vehicle TypeTrain	Travel Time5h 44m	Avg PriceCOP 291,215	Daily Departures3

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 COP 291,215 on average. If you're on a budget, you'll find cheap tickets from COP 127,091. 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!