How much is the train ticket from Chicago to Winona?

The cheapest train tickets from Chicago to Winona start from R 638. The average price for this train route is around R 1 050. Busbud recommends booking your tickets in advance for a better chance to secure the lowest possible price.

How long is the train journey from Chicago to Winona?

The average train journey time from Chicago to Winona is 5h 35m, covering a distance of 405 km. The quickest train can get you there in 5h 29m and is operated by Amtrak .

Which train operators serve the Chicago to Winona 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 Chicago to Winona?

The earliest train from Chicago to Winona departs at 06:10. And the latest train departs at 15:05.

Train Chicago to Winona from R 597 | Refundable Tickets

Next train departures

Next departures from Chicago to Winona on 20 February
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	15:05	Chicago (Union Station), IL	5h 29m	20:34	Winona Station	CheapestFastest
Train	11:10	Chicago (Union Station), IL	5h 35m	16:45	Winona Station	No tags
Train	15:05	Chicago (Union Station), IL	5h 29m	20:34	Winona Station	No tags
Train	06:10	Chicago (Union Station), IL	10h 35m	16:45	Winona Station	No tags
Train	08:25	Chicago (Union Station), IL	8h 20m	16:45	Winona Station	No tags

Next departures from Chicago to Winona on 21 February
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:10	Chicago (Union Station), IL	5h 35m	16:45	Winona Station	Cheapest
Train	15:05	Chicago (Union Station), IL	5h 29m	20:34	Winona Station	Fastest
Train	15:05	Chicago (Union Station), IL	5h 29m	20:34	Winona Station	No tags
Train	08:25	Chicago (Union Station), IL	8h 20m	16:45	Winona Station	No tags

Next departures from Chicago to Winona on 22 February
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:10	Chicago (Union Station), IL	5h 35m	16:45	Winona Station	Cheapest
Train	15:05	Chicago (Union Station), IL	5h 29m	20:34	Winona Station	Fastest
Train	15:05	Chicago (Union Station), IL	5h 29m	20:34	Winona Station	No tags
Train	08:25	Chicago (Union Station), IL	8h 20m	16:45	Winona Station	No tags

Next departures from Chicago to Winona on 23 February
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	15:05	Chicago (Union Station), IL	5h 29m	20:34	Winona Station	CheapestFastest
Train	11:10	Chicago (Union Station), IL	5h 35m	16:45	Winona Station	No tags
Train	15:05	Chicago (Union Station), IL	5h 29m	20:34	Winona Station	No tags
Train	06:10	Chicago (Union Station), IL	10h 35m	16:45	Winona Station	No tags
Train	08:25	Chicago (Union Station), IL	8h 20m	16:45	Winona Station	No tags

Next departures from Chicago to Winona on 24 February
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:10	Chicago (Union Station), IL	5h 35m	16:45	Winona Station	Cheapest
Train	15:05	Chicago (Union Station), IL	5h 29m	20:34	Winona Station	Fastest
Train	15:05	Chicago (Union Station), IL	5h 29m	20:34	Winona Station	No tags
Train	06:10	Chicago (Union Station), IL	10h 35m	16:45	Winona Station	No tags
Train	08:25	Chicago (Union Station), IL	8h 20m	16:45	Winona Station	No tags

Next departures from Chicago to Winona on 25 February
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:10	Chicago (Union Station), IL	5h 35m	16:45	Winona Station	Cheapest
Train	15:05	Chicago (Union Station), IL	5h 29m	20:34	Winona Station	Fastest
Train	15:05	Chicago (Union Station), IL	5h 29m	20:34	Winona Station	No tags
Train	06:10	Chicago (Union Station), IL	10h 35m	16:45	Winona Station	No tags
Train	08:25	Chicago (Union Station), IL	8h 20m	16:45	Winona Station	No tags

Next departures from Chicago to Winona on 26 February
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:10	Chicago (Union Station), IL	5h 35m	16:45	Winona Station	Cheapest
Train	15:05	Chicago (Union Station), IL	5h 29m	20:34	Winona Station	Fastest
Train	15:05	Chicago (Union Station), IL	5h 29m	20:34	Winona Station	No tags
Train	06:10	Chicago (Union Station), IL	10h 35m	16:45	Winona Station	No tags
Train	08:25	Chicago (Union Station), IL	8h 20m	16:45	Winona Station	No tags

Last refresh of the prices: Today at 11:33 AM CST.

Compare 2 ways to travel from Chicago to Winona

We recommend taking the train

Among the sustainable travel choices, the Train stands out as a good way to reach Winona. The journey takes about 5 hours 35 minutes and with fares starting at just R 638, it presents an excellent value for a comfortable ride.

3train per day

5h 35mAverage duration

405 kmDistance

37kgCO₂ emissions

	Average price	Average duration	CO₂ emissions	Actions
Bus	Average priceR 3 044 - R 3 146	Average duration16h 45m	CO₂ emissions 10kg CO₂e
Train	Average priceR 638 - R 2 576	Average duration5h 35m	CO₂ emissions 37kg CO₂e

Train Companies

Amtrak

4/55 759 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

WiFi3.6

Based on 5759 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 638

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

Frequently asked questions about travelling from Chicago to Winona, MN 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 Chicago to Winona?
The cheapest train tickets from Chicago to Winona start from R 638. The average price for this train route is around R 1 050. Busbud recommends booking your tickets in advance for a better chance to secure the lowest possible price.
How long is the train journey from Chicago to Winona?
The average train journey time from Chicago to Winona is 5h 35m, covering a distance of 405 km. The quickest train can get you there in 5h 29m and is operated by Amtrak.
Which train operators serve the Chicago to Winona 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 Chicago to Winona?
The earliest train from Chicago to Winona departs at 06:10. And the latest train departs at 15:05.

Find cheapest prices for trains

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

Best price found

17/02

R 895

18/02

R 1 111

Today

R 1 376

20/02

R 1 376

21/02

R 730

22/02

R 2 121

23/02

R 1 111

24/02

R 597

The cheapest trip from Chicago to Winona, MN was searched and found on 24 Feb 2026 with a price of R 597

To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Chicago to Winona, MN as early as possible.

You can expect to pay from R 597 to R 3 663 for a train ticket from Chicago to Winona, MN based on the last 2 days. You can expect to find the cheapest price for the trip at R 597, which is on 2026-02-24.

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

The Train is the cheapest travel choice for this destination

Vehicle type	Travel time	Avg price	Daily departures
Vehicle typeBus	Travel time16h 45m	Avg priceR 3 044	Daily departures1
Vehicle typeTrain	Travel time5h 35m	Avg priceR 1 050	Daily departures3

The best way to travel between Chicago and Winona, MN 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 1 050 on average. If you're on a budget, you'll find cheap tickets from R 638. If you're looking for the fastest way to get to Winona, MN, choose the train, as it will take you from Chicago to Winona, MN in about 5h 35m – that's the fastest way to get there!