Next departures for Chicago to Winona on November 19
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
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Train
Chicago (Union Station), IL
Winona Station
No tags
Train
Chicago (Union Station), IL
Winona Station
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Next departures for Chicago to Winona on November 20
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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
Next departures for Chicago to Winona on November 21
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
CheapestFastest
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
Train
Chicago (Union Station), IL
Winona Station
No tags
Next departures for Chicago to Winona on November 22
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
CheapestFastest
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
Next departures for Chicago to Winona on November 23
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
CheapestFastest
Train
Chicago (Union Station), IL
Winona Station
No tags
Next departures for Chicago to Winona on November 24
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 5:04 PM CST.
Compare 2 ways to go from Chicago to Winona
We recommend taking the train
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.
Based on 5593 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
How much does a train ticket from Chicago to Winona cost?
The average train ticket price from Chicago to Winona is $80. The best way to find train tickets from Chicago to Winona is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the train trip from Chicago to Winona?
A train trip between Chicago and Winona is around 5h 35m, although the fastest train will take about 5h 29m. This is the time it takes to travel the 253 miles that separates the two cities.
How many daily trains are there between Chicago and Winona?
The number of trains from Chicago to Winona can differ depending on the day of the week. On average, there are 3. Some trains are direct while others have layovers. Simplify your train trip from Chicago to Winona by comparing and selecting the train that fits your travel style and budget on Busbud.
Which train companies travel from Chicago to Winona?
When taking the train from Chicago to Winona, you can travel comfortably and safely with Amtrak.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
11/16
$149
11/17
$103
Today
$67
11/19
$36
11/20
$67
11/21
$103
11/22
$103
11/23
$149
The cheapest trip from Chicago to Winona, MN was searched and found on Nov 19, 2025 with a price of $36
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 $36 to $619 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 $36 which is on 2025-11-19.
What's the cheapest way to go from Chicago to Winona, MN?
The train is the cheapest travel choice for this destination
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 $80 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!