Next train departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Train | Chicago (Union Station), IL | Winona Station | Cheapest | ||||
| Train | Chicago (Union Station), IL | Winona Station | Fastest |
Last refresh of the prices: Today at 1:09 PM CDT.
Compare 2 ways to travel from Chicago to Winona
Among the sustainable travel choices, the Train stands out as a good way to reach Winona. The journey takes about 5 hours 50 minutes and with fares starting at just DKK 255, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5824 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 DKK 255
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 DKK 255. The average price for this train route is around DKK 584. 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 50m, 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.
The cheapest trip from Chicago to Winona, MN was searched and found on 17 Jun 2026 with a price of DKK 239To 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 DKK 239 to DKK 4 100 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 DKK 239, which is on 2026-06-17.
What's the cheapest way to go from Chicago to Winona, MN?
The Train is the cheapest travel choice for this destinationThe 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 DKK 584 on average. If you're on a budget, you'll find cheap tickets from DKK 255. 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 50m – that's the fastest way to get there!
