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

The average train ticket price from Winona to Chicago is $102. The best way to find cheap train tickets from Winona to Chicago 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 Winona to Chicago?

A train trip between Winona and Chicago is around 5h 44m, although the fastest train will take about 5h 34m. This is the time it takes to travel the 408 km that separates the two cities.

How many daily trains are there between Winona and Chicago?

The number of trains from Winona to Chicago 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 Winona to Chicago by comparing and selecting the train that fits your travel style and budget on Busbud.

Which train companies travel from Winona to Chicago?

When taking the train from Winona to Chicago, you can travel comfortably and safely with Amtrak.

Train Winona to Chicago from $52 | Refundable Tickets

Next train departures

Next departures for Winona to Chicago on November 20
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	1:41pm	Winona Station	5h 40m	7:21pm	Chicago (Union Station), IL	CheapestFastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags
Train	1:41pm	Winona Station	7h 23m	9:04pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on November 21
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended	Price and booking link
	Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Cheapest
	Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Fastest

Next departures for Winona to Chicago on November 22
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	Cheapest
Train	1:41pm	Winona Station	5h 40m	7:21pm	Chicago (Union Station), IL	Fastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on November 23
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Cheapest
Train	1:41pm	Winona Station	5h 40m	7:21pm	Chicago (Union Station), IL	Fastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on November 24
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	1:41pm	Winona Station	5h 40m	7:21pm	Chicago (Union Station), IL	CheapestFastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on November 25
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	1:41pm	Winona Station	5h 40m	7:21pm	Chicago (Union Station), IL	CheapestFastest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags

Next departures for Winona to Chicago on November 26
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Cheapest
Train	11:01am	Winona Station	5h 44m	4:45pm	Chicago (Union Station), IL	Fastest
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags
Train	11:01am	Winona Station	8h 20m	7:21pm	Chicago (Union Station), IL	No tags

Last refresh of the prices: Yesterday at 8:57 PM CST.

Compare 2 ways to go from Winona to Chicago

We recommend taking the train

Among the sustainable travel choices, the train stands out as a good way to reach Chicago. The journey takes about 5 hours 44 minutes, and with fares starting at just $56, it presents an excellent value for a comfortable ride.

3train per day

5h 44mAverage Duration

405 kmDistance

37kgCO₂ emissions

	Average Price	Average Duration	CO₂ emissions	Actions
Bus	Average Price$265 - $265	Average Duration16h 20m	CO₂ emissions 10kg CO₂e
Train	Average Price$56 - $421	Average Duration5h 44m	CO₂ emissions 37kg CO₂e

Train companies

Amtrak

4/55,594 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

Wifi3.6

Based on 5594 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 about travelling from Winona, MN to Chicago by train

How much does a cheap train ticket from Winona to Chicago cost?
The average train ticket price from Winona to Chicago is $102. The best way to find cheap train tickets from Winona to Chicago 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 Winona to Chicago?
A train trip between Winona and Chicago is around 5h 44m, although the fastest train will take about 5h 34m. This is the time it takes to travel the 408 km that separates the two cities.
How many daily trains are there between Winona and Chicago?
The number of trains from Winona to Chicago 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 Winona to Chicago by comparing and selecting the train that fits your travel style and budget on Busbud.
Which train companies travel from Winona to Chicago?
When taking the train from Winona to Chicago, 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

11-17

$97

11-18

$78

Today

$78

11-20

$185

11-21

$215

11-22

$121

11-23

$149

11-24

$52

The cheapest trip from Winona, MN to Chicago was searched and found on Nov 24, 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 Winona, MN to Chicago, as early as possible.

You can expect to pay from $52 to $475 for a train ticket from Winona, MN to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $52 which is on 2025-11-24.

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

The train is the cheapest travel choice for this destination

Vehicle Type	Travel time	Avg Price	Daily Departures
Vehicle TypeBus	Travel time16h 20m	Avg Price$265	Daily Departures1
Vehicle TypeTrain	Travel time5h 44m	Avg Price$102	Daily Departures3

The best way to travel between Winona, MN and Chicago is by train. By choosing the train, you'll get to save some money as you travel to your destination, as ticket prices cost $102 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 Chicago, choose the train, as it will take you from Winona, MN to Chicago in about 5h 44m —that's the fastest way to get there!