Next departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Winona Station | Chicago (Union Station), IL | CheapestFastest | |||||
| Winona Station | Chicago (Union Station), IL | No tags | |||||
| Winona Station | Chicago (Union Station), IL | No tags | |||||
| Winona Station | Chicago (Union Station), IL | No tags | |||||
| Winona Station | Chicago (Union Station), IL | No tags |
Last refresh of the prices: Yesterday at 8:39 PM CST.
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Compare 2 ways to travel from Winona to Chicago
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 US$39, it presents an excellent value for a comfortable ride.
Train Winona, MN to Chicago: Trip Overview
Please note, this information is subject to change.
Train Companies
Based on 5563 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 Wi-Fi. Amtrak ticket prices on this trip start at US$39
Winona to Chicago Train
With Busbud, comparing and booking tickets for a train from Winona to Chicago 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 services from Winona to Chicago.
From train tickets to high-end trains trip from Winona to Chicago, we offer a wide range of train services to best suit your needs depending on how much your budget is.
Frequently asked questions on the trip Winona, MN - Chicago
How much does a cheap train ticket from Winona to Chicago cost?
The average train ticket price from Winona to Chicago is US$71. 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 train 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 train 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.
The cheapest trip from Winona, MN to Chicago was searched and found on 08 Nov 2025 with a price of US$36To 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 US$36 to US$270 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 US$36, which is on 2025-11-08.
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 Winona to Chicago 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 Chicago, 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.
The train emits up to 30x less CO2 for a trip between Winona and Chicago compared to the same trip made by plane or car. A truly ecological mode of transport that will allow you to easily reduce your carbon footprint.
Tune out to the fine sounds of your best music playlist on your train trip from Winona to Chicago while indulging in miles on end of beautiful scenic views.
Did you know?
New York holds the record for the most platforms and track numbers in a single station. Grand Central Station in Manhattan is one of the largest rail terminals in the world with more than 44 platforms and 67 tracks to accommodate passengers.
Railway companies played a major role as early as 1883 in the use of time zones as we know them today.
Japanese trains are always on time. It is extremely infrequent to see breakdowns during peak periods. In the event of a delay of more than 5 minutes, the crew will personally apologise to each passenger.
What's the cheapest way to go from Winona, MN to Chicago?
The train is the cheapest travel choice for this destinationThe 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 US$71 on average. If you're on a budget, you'll find cheap tickets from US$39. 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!
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