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 | ||||
| Train | Chicago (Union Station), IL | Winona Station | No tags | ||||
| Train | Chicago (Union Station), IL | Winona Station | No tags | ||||
| Train | Chicago (Union Station), IL | Winona Station | No tags |
Last refresh of the prices: Yesterday at 1:55 PM CST.
Compare 2 ways to go from Chicago to Winona
Among the sustainable travel choices, the train stands out as the good way to reach Winona. The journey takes about 5 hours 35 minutes and with fares starting at just $39, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5623 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $39
Frequently asked questions about traveling from Chicago to Winona, MN 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 Chicago to Winona?
The cheapest train tickets from Chicago to Winona start from $39. The average price for this train route is around $82. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the train journey from Chicago to Winona?
The average train ride duration from Chicago to Winona is 5h 35m, covering a distance of 251 miles (405 km). The quickest train can get you there in 5h 29m and is operated by Amtrak.
Which train operators service the Chicago to Winona route?
Several major train operators operate on this route with 3 trains available per day.
What is the earliest and latest departure time for the train from Chicago to Winona?
The earliest train departs from Chicago to Winona at 6:10am. And the latest train departs at 3:05pm.
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 Dec 8, 2025 with a price of $54To 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 $54 to $604 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 $54 which is on 2025-12-08.
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 $82 on average. If you're on a budget, you'll find cheap tickets from $39. 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!
