How much does a cheap train ticket from Chicago to Winona cost?

The average train ticket price from Chicago to Winona is $115. The best way to find cheap 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 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 408 km 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 include transferring trains. 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.

Train Chicago to Winona from $52 | Refundable Tickets

Next train departures

Next departures for Chicago to Winona on November 14
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:10am	Chicago (Union Station), IL	5h 35m	4:45pm	Winona Station	Cheapest
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	Fastest
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	No tags
Train	6:10am	Chicago (Union Station), IL	10h 35m	4:45pm	Winona Station	No tags
Train	8:25am	Chicago (Union Station), IL	8h 20m	4:45pm	Winona Station	No tags

Next departures for Chicago to Winona on November 15
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:10am	Chicago (Union Station), IL	5h 35m	4:45pm	Winona Station	Cheapest
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	Fastest
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	No tags
Train	8:25am	Chicago (Union Station), IL	8h 20m	4:45pm	Winona Station	No tags

Next departures for Chicago to Winona on November 16
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	CheapestFastest
Train	11:10am	Chicago (Union Station), IL	5h 35m	4:45pm	Winona Station	No tags
Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	No tags
Train	8:25am	Chicago (Union Station), IL	8h 20m	4:45pm	Winona Station	No tags

Last refresh of the prices: Last Sunday at 6:09 AM 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 a good way to reach Winona. The journey takes about 5 hours 35 minutes, and with fares starting at just $56, 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 Price$264 - $264	Average Duration16h	CO₂ emissions 10kg CO₂e
Train	Average Price$56 - $899	Average Duration5h 35m	CO₂ emissions 37kg CO₂e

Train companies

Amtrak

4/55,583 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

Wifi3.6

Based on 5583 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 WiFi. Amtrak ticket prices on this trip start at $56

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

Frequently asked questions on the trip Chicago - Winona, MN

How much does a cheap train ticket from Chicago to Winona cost?
The average train ticket price from Chicago to Winona is $115. The best way to find cheap 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 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 408 km 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 include transferring trains. 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

11-11

$97

11-12

$64

Today

$120

11-14

$52

11-15

$97

11-16

$148

11-17

$64

11-18

$64

The cheapest trip from Chicago to Winona, MN was searched and found on Nov 14, 2025 with a price of $52

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 $52 to $462 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 $52 which is on 2025-11-14.

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	Avg Price$264	Daily Departures1
Vehicle TypeTrain	Travel time5h 35m	Avg Price$115	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 $115 on average. If you're on a budget, you'll find cheap tickets from $56. 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!