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Trip Summary
There are usually 4 daily train trips available from Naperville to Winona. Traveling by train from Naperville to Winona usually takes 10 hours and 10 minutes, but the fastest Amtrak train can make the trip in 9 hours and 54 minutes.
| Distance | 239 mi (384 km) |
| Fastest train | 9h 54m |
| Lowest price | $76.00 |
| Most frequent service | Amtrak |
| Train lines | 1 |
Which train should you take from Naperville to Winona?
Amtrak is the one and only train line which connects Naperville to Winona. However, there are 4 trains per day to choose from.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 4 | 10h 10m | $104.75 |
Amtrak is the largest passenger railroad service in America, offering daily intercity trains to hundreds of destinations across the contiguous United States, as well as several cities in Canada. Every Amtrak train comes equipped with comfortable seats with extra legroom, as well as several four-seat areas with tables in the middle. In addition, each car has a freshly cleaned restroom, free WiFi and power outlets at every seat. There are also snack bars where you can purchase drinks or food during your journey. On average, there are 4 Amtrak trains from Naperville to Winona every day, as well as 4 trips on the weekends, with prices starting from $76.
Frequently Asked Questions
The distance between Naperville and Winona is approximately 239 miles, or 384 kilometers. The average train journey between these two cities takes 10 hours and 10 minutes, although the absolute fastest you could get there is 9 hours and 54 minutes.
Looking for ways to pass the time? Most trains are equipped with Wi-Fi, which means you can stream music, browse social media or get some work done during your ride. That said, in case your train has a spotty signal, or is among the few without Wi-Fi, we also recommend downloading TV shows and movies to your mobile device in advance of your trip. That way the ride will fly by whatever the Wi-Fi situation.
Trains departing from Naperville to Winona tend to have the most passengers on Monday. With higher demand ticket prices also tend to be higher on Monday. If you are trying to snag a cheap train tickets or just want an emptier train you'll have better luck by booking travel departing on Tuesday as the least number of people tend to travel then.
The earliest train departs Naperville at 9:00am while the last train of the day leaves at 9:00am. To see all scheduled departure times, use the search function on this page to get the full schedule for your specific travel dates.
There are 4 scheduled trains on most days. Unfortunately, none of them are direct connections, so you will need to disembark from your original train and board a connecting train during your journey. Don't forget to bring your carry-on luggage when you switch trains. In some instances, you may also be responsible for transferring your own checked baggage.
You can also take a train for your return trip from Winona to Naperville.
City Information
Station Information
Where is the train station in Naperville?
Main departure station: 105 E Fourth Ave
There is one train station in Naperville.
All train stations in Naperville:
105 E Fourth Ave
Where is the train station in Winona?
Main arrival station: 65 E Mark St
Winona has one train station.
All train stations in Winona:
65 E Mark St
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