Cheap train tickets from Winona to Chicago
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Trip Summary
There are usually 5 daily train trips available from Winona to Chicago. Traveling by train from Winona to Chicago usually takes 6 hours and 38 minutes, but the fastest Amtrak Borealis train can make the trip in 5 hours and 40 minutes.
| Distance | 253 mi (408 km) |
| Fastest train | 5h 40m |
| Lowest price | $36.00 |
| Trains per day | 3 |
| Most frequent service | Amtrak |
| Train lines | 3 |
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Winona to Chicago Train Schedule
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There are several train options that can take you from Winona to Chicago:
- Amtrak: 3 daily trains from $50
- Amtrak Empire Builder: 2 daily trains from $67
- Amtrak Borealis: 1 daily train from $36
What is the price of a train ticket from Winona to Chicago?
In the last month, the average price of a train ticket from Winona to Chicago was $66.33. Good news! You can find the cheapest tickets if you book your trip at least 21 days prior to the travel date. You’ll likely pay around $191.69 more if you wait to book until the last minute.
Average train ticket prices from Winona to Chicago by travel date
Over the next 30 days, a one-way train trip from Winona to Chicago will cost between $59 and $135. Book in advance to secure the best price in the next few weeks.
Average train ticket prices from Winona to Chicago by month
Ticket prices for the train from Winona to Chicago 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 $78. If you're thinking of traveling from Winona to Chicago during December, keep in mind that train ticket prices may be higher than usual, with an average price of $120 during this time of year. The best way to score a cheap deal, even in December, is to book your trip well in advance.
Prices as travel date approaches
By booking your train trip from Winona to Chicago on Wanderu at least 21 days ahead of time, you can save about $191.69 on your ticket. Waiting until the last minute means missing out on these savings!
What train companies travel from Winona to Chicago?
There are multiple trains that travel from Winona to Chicago, including Amtrak, Amtrak Empire Builder, Amtrak Borealis. Here is what you should know about the 3 most popular train lines:
| TRAIN | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 3 | 7h 56m | $112.15 |
| Amtrak Empire Builder | 2 | 5h 44m | $223.67 |
| Amtrak Borealis | 1 | 5h 40m | $90.75 |
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 3 Amtrak trains from Winona to Chicago every day, as well as 3 trips on the weekends, with prices starting from $50.
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.
Amtrak Borealis train tickets from Winona to Chicago start from $36, and on average cost $90.75. Daily there are 1 Amtrak Borealis schedules to Chicago. Amtrak Borealis in Winona leaves from 65 E Mark St. And in Chicago trains arrive at Union Station.
From Winona to Chicago train travel on Amtrak Borealis takes 5 hours and 40 minutes.
If you are looking to travel to Chicago on a weekend there is typically one Amtrak Borealis scheduled trip per day, which will cost $36 for a one-way weekend reservation from Winona.
Frequently asked questions about traveling by train from Winona to Chicago
There are 5 scheduled trains on most days. 3 of these are direct connections to Chicago. 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 Chicago to Winona. If you're not set on traveling by train, you could always take the bus from Winona to Chicago for $179.
TRIPS PER DAY
5
DIRECT TRIPS
3
The distance between Winona and Chicago is approximately 253 miles, or 408 kilometers. The average train journey between these two cities takes 6 hours and 38 minutes, although the absolute fastest you could get there is 5 hours and 40 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)
253
DISTANCE (KM)
408
The earliest train departs Winona at 11:01am while the last train of the day leaves at 1:41pm. 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
11:01am
LATEST TRAIN
1:41pm
Trains from Winona to Chicago are the most crowded on Saturday. 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 Monday instead, as it tends to be the least crowded day of the week.
MOST CROWDED
Saturday
LEAST CROWDED
Monday
City Information
Chicago
Known for its innovative architecture, cultural contributions to jazz and house music, and of course that irresistible deep-dish pizza, the many sights and experiences in Chicago make it one of the best urban vacation destinations for millennials and a top destination in Illinois.
You can't beat the views of the city and Lake Michigan from the SkyDeck in the Willis Tower; at over 1,300 feet, this is the highest observation deck in the U.S. Snap that classic selfie with the Bean in Millennium Park, then wander the many museums in nearby Grant Park. Navy Pier is a popular tourist hotspot for its parks, restaurants, and attractions right on Lake Michigan, and baseball fans will find paradise in Wrigleyville, home to the Chicago Cubs' Wrigley Field and sports bars galore.
Chicago's enormous parks offer plentiful opportunities for outdoor activities in gorgeous urban settings. Many companies offer kayak rentals or boat tours on the Chicago River, with special tours running on Saint Patrick's Day, when the entire river is dyed green. When you’re ready to buy some souvenirs from your epic trip, hit the big brand stores on the Magnificent Mile, or shop local in neighborhoods like Andersonville and Wicker Park. And don't miss the chance to laugh until you cry at The Second City comedy theater, famous for launching the careers of comedians like Tina Fey and Stephen Colbert.
Chicago is one of the biggest transportation hubs in the Midwest, and provides easy access to nearby destinations ideal for day trips, as well as international travel from two airports. Thanks to plenty of bus and train stations throughout the city, getting to the Windy City is a breeze.
Station Information
Where does the train leave from in Winona?
Main departure station: 65 E Mark St
There is one train station in Winona.
All train stations in Winona:
- 65 E Mark St
Where does the train arrive in Chicago?
Main arrival station: Union Station
The historic Chicago Union Station is the United States' third busiest train station and a hub for 15 Amtrak train lines with destinations throughout the country. The station also serves bus carriers like Greyhound, Indian Trails and Jefferson Lines, and offers connections to Metra commuter lines. Union Station is also just a quick walk to the nearest Chicago L lines. The current station was built in 1925, to replace the original one dating back to 1881, and today wows visitors with its impressive facade, massive columns, and opulent Great Hall. Located right in downtown and adjacent to the Chicago Loop, Union Station is equipped with many services and amenities, including phone charging stations, shops, and various food and drink options.
All train stations in Chicago:
- Union Station
Need a return trip from Chicago to Winona?
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