Next train departures

Next departures from Winona to Chicago on 19 October
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wifi Toilet Power outlets	13:41	Winona Station	5h 50m	19:31	Chicago (Union Station), IL	Cheapest
Train Wifi Toilet Power outlets	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	Fastest
Train Wifi Toilet Power outlets	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	8h 30m	19:31	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	8h 30m	19:31	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	13:41	Winona Station	7h 33m	21:14	Chicago (Union Station), IL	No tags

Next departures from Winona to Chicago on 20 October
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wifi Toilet Power outlets	13:41	Winona Station	5h 50m	19:31	Chicago (Union Station), IL	Cheapest
Train Wifi Toilet Power outlets	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	Fastest
Train Wifi Toilet Power outlets	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	8h 30m	19:31	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	8h 30m	19:31	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	13:41	Winona Station	7h 33m	21:14	Chicago (Union Station), IL	No tags

Next departures from Winona to Chicago on 21 October
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wifi Toilet Power outlets	13:41	Winona Station	5h 50m	19:31	Chicago (Union Station), IL	Cheapest
Train Wifi Toilet Power outlets	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	Fastest
Train Wifi Toilet Power outlets	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	8h 30m	19:31	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	8h 30m	19:31	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	8h 30m	19:31	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	13:41	Winona Station	7h 33m	21:14	Chicago (Union Station), IL	No tags

Next departures from Winona to Chicago on 22 October
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wifi Toilet Power outlets	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	CheapestFastest
Train Wifi Toilet Power outlets	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	13:41	Winona Station	5h 50m	19:31	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	8h 30m	19:31	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	8h 30m	19:31	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	8h 30m	19:31	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	13:41	Winona Station	7h 33m	21:14	Chicago (Union Station), IL	No tags

Next departures from Winona to Chicago on 23 October
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wifi Toilet Power outlets	11:01	Winona Station	8h 30m	19:31	Chicago (Union Station), IL	Cheapest
Train Wifi Toilet Power outlets	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	Fastest
Train Wifi Toilet Power outlets	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	13:41	Winona Station	5h 50m	19:31	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	8h 30m	19:31	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	13:41	Winona Station	7h 33m	21:14	Chicago (Union Station), IL	No tags

Next departures from Winona to Chicago on 24 October
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wifi Toilet Power outlets	13:41	Winona Station	5h 40m	19:21	Chicago (Union Station), IL	CheapestFastest
Train Wifi Toilet Power outlets	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	8h 20m	19:21	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	8h 20m	19:21	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	13:41	Winona Station	7h 23m	21:04	Chicago (Union Station), IL	No tags

Next departures from Winona to Chicago on 25 October
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wifi Toilet Power outlets	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	Cheapest
Train Wifi Toilet Power outlets	13:41	Winona Station	5h 40m	19:21	Chicago (Union Station), IL	Fastest
Train Wifi Toilet Power outlets	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	8h 20m	19:21	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	11:01	Winona Station	8h 20m	19:21	Chicago (Union Station), IL	No tags
Train Wifi Toilet Power outlets	13:41	Winona Station	7h 23m	21:04	Chicago (Union Station), IL	No tags

Last refresh of the prices: Today at 12:46 AM CDT.

Compare 2 ways to travel 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 50 minutes and with fares starting at just R 651, it presents an excellent value for a comfortable ride.

4train per day

5h 50mAverage duration

405 kmDistance

37kgCO₂ emissions

	Average price	Average duration	CO₂ emissions	Actions
Bus	Average priceR 2 084 - R 3 106	Average duration15h 45m	CO₂ emissions 10kg CO₂e
Train	Average priceR 651 - R 8 158	Average duration5h 50m	CO₂ emissions 37kg CO₂e

Train Companies

Amtrak

4.1/56 575 reviews

Staff4.7

Timeliness3.8

Cleanliness4.5

WiFi3.6

Based on 6575 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained about the Wi-Fi. Amtrak ticket prices on this trip start at R 651

US train companies: Amtrak, Amtrak Acela, Brightline

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

Please note that timetables, routes, or operator details shown here may be updated or differ 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 R 651. The average price for this train route is around R 1 193. Busbud recommends booking your tickets in advance for a better chance to secure the lowest possible price.
How long is the train journey from Winona to Chicago?
The average train journey time from Winona to Chicago is 5h 50m, covering a distance of 405 km. The quickest train can get you there in 5h 40m and is operated by Amtrak.
Which train operators serve the Winona to Chicago route?
Several major train operators run on 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 11:01. And the latest train departs at 13:41.

Find cheapest prices for trains

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

Best price found

15/10

R 1 404

16/10

R 1 133

Today

R 609

18/10

R 1 133

19/10

R 744

20/10

R 609

21/10

R 609

22/10

R 1 742

The cheapest trip from Winona, MN to Chicago was searched and found on 17 Oct 2026 with a price of R 609

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 R 609 to R 10 584 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 R 609, which is on 2026-10-20.

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 priceR 3 106	Daily departures1
Vehicle typeTrain	Travel time5h 50m	Avg priceR 1 193	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 R 1 193 on average. If you're on a budget, you'll find cheap tickets from R 651. 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 50m – that's the fastest way to get there!