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One passenger / one way
- This trip is recommended because it is the: CheapestDeparture time: April 28 atDeparture city: ChicagoDeparture location: Chicago (Union Station), ILArrival time: April 28 atDestination city: WinonaDestination location: Winona StationOperated by: Amtrak
Vehicle: TrainDuration: - This trip is recommended because it is the: FastestDeparture time: April 28 atDeparture city: ChicagoDeparture location: Chicago (Union Station), ILArrival time: April 28 atDestination city: WinonaDestination location: Winona StationOperated by: AmtrakVehicle: TrainDuration:
- Departure time: April 28 atDeparture city: ChicagoDeparture location: Chicago (Union Station), ILArrival time: April 28 atDestination city: WinonaDestination location: Winona StationOperated by: AmtrakVehicle: TrainDuration:
- Departure time: April 28 atDeparture city: ChicagoDeparture location: Chicago (Union Station), ILArrival time: April 28 atDestination city: WinonaDestination location: Winona StationOperated by: AmtrakVehicle: TrainDuration:
- Departure time: April 28 atDeparture city: ChicagoDeparture location: Chicago (Union Station), ILArrival time: April 28 atDestination city: WinonaDestination location: Winona StationOperated by: AmtrakVehicle: TrainDuration:
Last refresh of the prices: Yesterday at 7:42 PM CDT.
Prices and availability are subject to change.
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Train Chicago to Winona: Trip Overview
Please note, this information is subject to change
Train companies
Based on 5080 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 US$39.00
Chicago to Winona Train
With Busbud, comparing and booking tickets for a train from Chicago to Winona is a breeze. Browse through an extensive selection of train fares and train schedules to find the best deals.
We make it our job to connect you with the most dependable companies that offer train service from Chicago to Winona.
Whether it is train tickets or first class train tickets going to Winona from Chicago, we help you find what you're looking for based on how much of a budget you have.
Frequently asked questions on the trip Chicago - Winona
How much does a cheap train ticket from Chicago to Winona cost?
The average train ticket price from Chicago to Winona is US$88. 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 2. 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.
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 was searched and found on Apr 26, 2025 with a price of US$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, as early as possible.
You can expect to pay from US$54 to US$248 for a train ticket from Chicago to Winona based on the last 2 days. You can expect to find the cheapest price for the trip at US$54 which is on 2025-04-28.
About Train Travel
Train Travel Tips
Taking the fastest trains allows you to travel at speeds greater than 300 km/h. Taking a trip from Chicago to Winona is not only much quicker but more comfortable too! You can usually travel directly to the city centre and save time while you're at it.
Whether you take a regional or high-speed train to Winona, you’ll help reduce the environmental impact and carbon footprint of your trip. As you watch the landscapes unfold before your eyes, you can tell yourself that with this choice, you are making sure they remain protected.
By choosing the train between Chicago and Winona, you emit up to 30 times less CO2 than for the same journey made by plane or car!
Tune out to the fine sounds of your best music playlist on your train trip from Chicago to Winona while indulging in miles on end of beautiful scenic views.
Did you know?
Railway companies played a major role as early as 1883 in the use of time zones as we know them today.
You can find the straightest railway in the world in Australia. This railway line is 478 kilometres long and is also considered the longest and straightest railway line in the world.
The first high-speed train line was inaugurated in 1964, in Japan, to connect Tokyo with Osaka. It was during the Olympics that the first passengers travelled aboard the Shinkansen at a speed of 210 km / h.
Top Travelled Train Routes
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