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.

Train Chicago to Winona from $36 | Refundable Tickets

Next train departures

Next departures for Chicago to Winona on November 19
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 20
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 21
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	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 22
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

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	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	CheapestFastest
	Train	3:05pm	Chicago (Union Station), IL	5h 29m	8:34pm	Winona Station	No tags

Next departures for Chicago to Winona on November 24
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

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.

3train per day

5h 35mAverage Duration

251 milesDistance

37kgCO₂ emissions

	Average Price	Average Duration	CO₂ emissions	Actions
Bus	Average Price$184 - $203	Average Duration16h 15m	CO₂ emissions 10kg CO₂e
Train	Average Price$39 - $156	Average Duration5h 35m	CO₂ emissions 37kg CO₂e

Train Companies

Amtrak

4/55,593 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

Wifi3.6

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

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

Frequently asked questions about traveling from Chicago to Winona, MN by train

How much does a train ticket from Chicago to Winona cost?
How long is the train trip from Chicago to Winona?
How many daily trains are there between Chicago and Winona?
Which train companies travel from Chicago to Winona?

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

Vehicle Type	Travel Time	Avg Price	Daily Departures
Vehicle TypeBus	Travel Time16h 15m	Avg Price$184	Daily Departures1
Vehicle TypeTrain	Travel Time5h 35m	Avg Price$80	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 $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!