Next train departures

Next departures for Winona to Chicago on August 8
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	1:41pm	Winona Station	7h 23m	9:04pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on August 9
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 August 10
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 August 11
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 August 12
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 August 13
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended	Price and booking link
	Train	1:41pm	Winona Station	7h 23m	9:04pm	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 August 14
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 August 15
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	Cheapest
Train	1:41pm	Winona Station	5h 40m	7:21pm	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	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 10:11 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 MAD 367, it presents an excellent value for a comfortable ride.

3train per day

5h 44mAverage Duration

405 kmDistance

37kgCO₂ emissions

	Average Price	Average Duration	CO₂ emissions	Actions
Bus	Average PriceMAD 1,752 - MAD 1,752	Average Duration15h 45m	CO₂ emissions 10kg CO₂e
Train	Average PriceMAD 367 - MAD 5,974	Average Duration5h 44m	CO₂ emissions 37kg CO₂e

Train companies

Amtrak

4.1/56,394 reviews

Staff4.7

Timeliness3.8

Cleanliness4.5

Wi‑Fi3.6

Based on 6394 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 MAD 367

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 MAD 367. The average price for this train route is around MAD 782. 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 44m and covers 405 km. The quickest train gets you there in 5h 40m and is operated by Amtrak.
Which train operators serve the Winona to Chicago route?
Several major train operators serve this route, with 3 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

08-06

MAD 4,130

08-07

MAD 8,327

Today

MAD 983

08-09

MAD 1,422

08-10

MAD 640

08-11

MAD 983

08-12

MAD 983

08-13

MAD 1,269

The cheapest trip from Winona, MN to Chicago was searched and found on Aug 10, 2026 with a price of MAD 640

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 MAD 640 to MAD 8,327 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 MAD 640 which is on 2026-08-10.

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 PriceMAD 1,752	Daily Departures1
Vehicle TypeTrain	Travel time5h 44m	Avg PriceMAD 782	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 MAD 782 on average. If you're on a budget, you'll find cheap tickets from MAD 367. 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!