Cheap train tickets from Milwaukee to Winona
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Trip Summary
There are usually 6 daily train trips available from Milwaukee to Winona. Traveling by train from Milwaukee to Winona usually takes 6 hours and 8 minutes, but the fastest Amtrak Empire Builder train can make the trip in 3 hours and 49 minutes.
| Distance | 201 mi (323 km) |
| Fastest train | 3h 49m |
| Lowest price | $29.00 |
| Trains per day | 2 |
| Most frequent service | Amtrak |
| Train lines | 3 |
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Milwaukee to Winona Train Schedule
Is it better to travel by train or bus from Milwaukee to Winona?
There are usually 1 daily bus trips available from Milwaukee to Winona.
Train | Bus | |
|---|---|---|
Avg. Price | Avg. Price$90.79Cheaper | Avg. Price$103.00 |
Daily Trips | Daily Trips6 | Daily Trips1 |
Duration | Duration6h 8m | Duration5h 5mFaster |

There are several train options that can take you from Milwaukee to Winona:
- Amtrak: 4 daily trains from $36
- Amtrak Borealis: 1 daily train from $29
- Amtrak Empire Builder: 2 daily trains from $29
What is the price of a train ticket from Milwaukee to Winona?
In the last month, the average price of a train ticket from Milwaukee to Winona was $55.61. Good news! You can find the cheapest tickets if you book your trip at least 29 days prior to the travel date. You’ll likely pay around $85.42 more if you wait to book until the last minute.
Average train ticket prices from Milwaukee to Winona by travel date
Over the next 30 days, a one-way train trip from Milwaukee to Winona will cost between $33 and $122. Book in advance to secure the best price in the next few weeks.
Average train ticket prices from Milwaukee to Winona by month
Ticket prices for the train from Milwaukee to Winona often fluctuate based on the time of year. For the best prices on this route, book in February when the average ticket price is only $55. If you're thinking of traveling from Milwaukee to Winona during June, keep in mind that train ticket prices may be higher than usual, with an average price of $85 during this time of year. The best way to score a cheap deal, even in June, is to book your trip well in advance.
Prices as travel date approaches
By booking your train trip from Milwaukee to Winona on Wanderu at least 29 days ahead of time, you can save about $85.42 on your ticket. Waiting until the last minute means missing out on these savings!
What train companies travel from Milwaukee to Winona?
There are multiple trains that travel from Milwaukee to Winona, including Amtrak, Amtrak Borealis, Amtrak Empire Builder. Here is what you should know about the 3 most popular train lines:
| TRAIN | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 4 | 7h 4m | $85.34 |
| Amtrak Borealis | 1 | 4h 14m | $81.20 |
| Amtrak Empire Builder | 2 | 3h 49m | $152.99 |
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 Milwaukee to Winona every day, as well as 3 trips on the weekends, with prices starting from $36.










Amtrak Borealis train tickets from Milwaukee to Winona start from $29, and on average cost $81.20. Daily there are 1 Amtrak Borealis schedules to Winona. Amtrak Borealis in Milwaukee leaves from Airport - 5601 S 6th St and one other station. And in Winona trains arrive at 65 E Mark St.
From Milwaukee to Winona train travel on Amtrak Borealis takes 4 hours and 14 minutes. If you are looking to get to Winona faster, Amtrak Borealis offers more express schedule options with a travel time of 3 hours and 56 minutes.
If you're considering a weeked trip, Amtrak Borealis offers 2 schedules for you to choose from. You can expect to pay $29 for a one-way train ticket to Winona.
The Amtrak Empire Builder is a long-distance passenger rail service that has been in operation since 1929. The full 2,200-mile route takes 45 hours to connect Chicago with the Pacific Northwest. Don’t let the length of the trip intimidate you; the Empire Builder is one of Amtrak’s most popular services, and often rated as the most scenic train route in the country. The sightseer lounge, home to enormous windows, is the perfect place to drink in the incredible views of the Mississippi River, the North Dakota Plains, Glacier National Park, and the Columbia River Gorge. Overnight trips on the Empire Builder include the option to book sleeper cabins, for a more comfortable journey and included meals. All passengers can purchase meals or snacks in the cafe car.
Frequently asked questions about traveling by train from Milwaukee to Winona
There are 6 scheduled trains on most days. 2 of these are direct connections to Winona. While direct trains may still make stops along the way, you will not need to switch trains at any point. If you're looking to get to your destination faster, a direct train is the convenient and time-efficient choice. You can also take a train for your return trip from Winona to Milwaukee. If you're not set on traveling by train, you could always take the bus from Milwaukee to Winona for $103.
TRIPS PER DAY
6
DIRECT TRIPS
2
The distance between Milwaukee and Winona is approximately 201 miles, or 323 kilometers. The average train journey between these two cities takes 6 hours and 8 minutes, although the absolute fastest you could get there is 3 hours and 49 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.
DISTANCE (MI)
201
DISTANCE (KM)
323
The earliest train departs Milwaukee at 7:24am while the last train of the day leaves at 4:45pm. To see all scheduled departure times, use the search function on this page to get the full schedule for your specific travel dates.
EARLIEST TRAIN
7:24am
LATEST TRAIN
4:45pm
Trains from Milwaukee to Winona are the most crowded on Wednesday. Tickets also tend to be more expensive then. If you are looking for a great deal on your train tickets or just want extra room to stretch out, consider traveling on Friday instead, as it tends to be the least crowded day of the week.
MOST CROWDED
Wednesday
LEAST CROWDED
Friday
City Information
Milwaukee



Nestling on the banks of the great Lake Michigan, Milwaukee has some of the most scenic views around, making it every photographer’s perfect destination. Boasting 85 miles of scenic waterfront bike lanes, Milwaukee is the perfect spot to ride a bike and enjoy the sunset together with your friends. It is also the home of the Harley Davidson Museum, a vast waterfront gallery that offers 11 permanent exhibitions. The museum features not only bikes but also special items such as a whole engine room, making it a must-visit spot for bike enthusiasts. If you are not interested in bikes, the Basilica of St. Josaphat, which is modeled after St. Peter’s Basilica in the Vatican, offers many wondrous shots.
Milwaukee’s famous German bratwursts are a must-try for all visitors, and the best place to enjoy this dish is Usinger’s. Other similar establishments include Mader’s and Milwaukee Public Market. For authentic American eats, Leon's Frozen Custard Drive-In offers amazing sloppy-joe burgers.
The Milwaukee Intermodal Station is the city’s main transportation hub. Visitors can catch both buses and trains at this location. The city is served by two airports. The Milwaukee Mitchell International Airport on the southern edge of the city handles commercial flights, while the Lawrence J. Timmerman Airport in the northwest handles private flights.
Station Information
Where does the train leave from in Milwaukee?
Main departure station: Airport - 5601 S 6th St


The Milwaukee Airport Rail Station is located on the western edge of the Milwaukee Mitchell International Airport. The station serves as a rail link for the airport and also as a more accessible transport link for residents living in the south of Milwaukee compared to the central Intermodal Station. Amtrak’s Hiawatha Service is the only train that operates at the station and runs northwards to downtown Milwaukee and southwards to Chicago Union Station, where passengers can change for travel across the entire Midwest region. The airport station also has a shuttle service to the airport terminal.
All train stations in Milwaukee:
- Airport - 5601 S 6th St
- Intermodal Station - 433 W ST Paul Ave
Where does the train arrive in Winona?
Main arrival station: 65 E Mark St
Winona has one train station.
All train stations in Winona:
- 65 E Mark St
Need a return trip from Winona to Milwaukee?
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