How much is the train ticket from Winona to Chicago?

The cheapest train tickets from Winona to Chicago start from R 666. The average price for this train route is around R 1 221. 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 44m, covering a distance of 405 km. The quickest train can get you there in 5h 34m and is operated by Amtrak .

Which train operators serve the Winona to Chicago route?

Several major train operators run on 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 11:01. And the latest train departs at 13:41.

Train Winona to Chicago from R 623 | Refundable Tickets

Next train departures

Next departures from Winona to Chicago on 12 December
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	13:41	Winona Station	5h 40m	19:21	Chicago (Union Station), IL	CheapestFastest
Train	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train	13:41	Winona Station	7h 23m	21:04	Chicago (Union Station), IL	No tags

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

Next departures from Winona to Chicago on 14 December
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:01	Winona Station	8h 20m	19:21	Chicago (Union Station), IL	Cheapest
Train	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	Fastest
Train	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train	11:01	Winona Station	8h 20m	19:21	Chicago (Union Station), IL	No tags

Next departures from Winona to Chicago on 15 December
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	13:41	Winona Station	5h 40m	19:21	Chicago (Union Station), IL	CheapestFastest
Train	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train	11:01	Winona Station	8h 20m	19:21	Chicago (Union Station), IL	No tags
Train	11:01	Winona Station	8h 20m	19:21	Chicago (Union Station), IL	No tags

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

Next departures from Winona to Chicago on 17 December
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	13:41	Winona Station	5h 40m	19:21	Chicago (Union Station), IL	CheapestFastest
Train	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train	13:41	Winona Station	7h 23m	21:04	Chicago (Union Station), IL	No tags

Next departures from Winona to Chicago on 18 December
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	13:41	Winona Station	5h 40m	19:21	Chicago (Union Station), IL	CheapestFastest
Train	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train	11:01	Winona Station	5h 44m	16:45	Chicago (Union Station), IL	No tags
Train	11:01	Winona Station	8h 20m	19:21	Chicago (Union Station), IL	No tags
Train	11:01	Winona Station	8h 20m	19:21	Chicago (Union Station), IL	No tags

Last refresh of the prices: Yesterday at 7:45 PM CST.

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 44 minutes and with fares starting at just R 666, 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 priceR 3 177 - R 3 496	Average duration16h	CO₂ emissions 10kg CO₂e
Train	Average priceR 666 - R 2 688	Average duration5h 44m	CO₂ emissions 37kg CO₂e

Train Companies

Amtrak

4/55 637 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

WiFi3.6

Based on 5637 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 R 666

US train companies: Amtrak, Trenitalia, Renfe, VIA Rail Canada, Amtrak Acela, NS Nederlandse Spoorwegen, Iryo

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 666. The average price for this train route is around R 1 221. 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 44m, covering a distance of 405 km. The quickest train can get you there in 5h 34m and is operated by Amtrak.
Which train operators serve the Winona to Chicago route?
Several major train operators run on 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 11:01. 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

09/12

R 934

10/12

R 934

Today

R 1 782

12/12

R 934

13/12

R 1 436

14/12

R 1 453

15/12

R 934

16/12

R 1 159

The cheapest trip from Winona, MN to Chicago was searched and found on 09 Dec 2025 with a price of R 934

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 934 to R 4 670 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 934, which is on 2025-12-12.

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 time16h	Avg priceR 3 177	Daily departures1
Vehicle typeTrain	Travel time5h 44m	Avg priceR 1 221	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 R 1 221 on average. If you're on a budget, you'll find cheap tickets from R 666. 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!