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Cheap train tickets from Chicago to Winona

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4.8 Rating

5k Reviews

4.5 Rating

4.8k Reviews

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Chicago to Winona Train Schedule

Trip Summary

5 trains operate daily from Chicago to Winona. The train trip from Chicago to Winona is usually about 6 hours and 53 minutes long. However, traveling on the fastest Amtrak Empire Builder train can get you there in as little as 5 hours and 29 minutes.

Distance253 mi (408 km)
Fastest train5h 29m
Lowest priceHRK 227.49
Trains per day3
Most frequent serviceAmtrak Empire Builder
Train lines3

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Train Trip Reviews from Wanderu Customers

Average score for trains from Chicago to Winona

(Based on 6 ratings and reviews)

4.5

5.0

francis

November 25, 2025- Visiting family

Amtrak Empire Builder

Pros: conductors and staff couldn’t have been more helpful & friendly ! Cons: nothing I can think of.

4.0

Daniela

May 24, 2023- Vacation

Amtrak Empire Builder

Pros: Alternative to fly. Tips: Get a ticket in advance.

4.0

Mary

September 17, 2022- Visiting family

Amtrak Empire Builder

Pros: Very nice staff on board.. they smiled and were very positive and friendly and helpful :) I liked how spacious the seats were and the big windows! Cons: The food pricing (it’s so expensive!!). The set-up of the cafe (not enough room… people jammed in line). The Chicago train station was super confusing and most people were in the wrong line and the workers there were really rude and nonchalant/aloof. Tips: Bring your own food and snacks!

5.0

Dallas

December 8, 2019- Vacation

Amtrak Empire Builder

Pros: Never had been in a dining car. It was a great experience, great food and staff. Cons: Wifi. Tips: No, just get in and enjoy.

5.0

Susan

November 4, 2019- Visiting family

Amtrak Empire Builder

Pros: As fast as driving. Restful. Scenic. Cons: At stops permitting smoking, first let passengers off who are debarking. Tips: Amtrak seems to be trying to be more timely.

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What is the price of a train ticket from Chicago to Winona?

The average price for a train ticket from Chicago to Winona is HRK 334.85, By booking your trip at least 29 days in advance, you increase your chances of scoring even cheaper tickets. But if you wait until the day of your trip to book tickets, expect to pay HRK 230.96 more.

Average train ticket prices from Chicago to Winona by travel date

HRK 758HRK 506HRK 253JanFeb

For the next 30 days, the cost of a one-way train trip from Chicago to Winona will range from HRK 322 to HRK 670. If you're planning to travel by train to Winona in the upcoming week, the cheapest train ticket from Chicago you can find in the next 7 days is HRK 329. Be sure to book your trip in advance as train ticket prices typically increase as your travel date approaches.

Average train ticket prices from Chicago to Winona by month

HRK 632HRK 506HRK 379HRK 253HRK 126FMAMJJASONDJ
Ticket prices for the train from Chicago 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 HRK 398. If you're thinking of traveling from Chicago to Winona during August, keep in mind that train ticket prices may be higher than usual, with an average price of HRK 575 during this time of year. The best way to score a cheap deal, even in August, is to book your trip well in advance.

Prices as travel date approaches

HRK 790HRK 632HRK 474HRK 316HRK 1583020100

By booking your train trip from Chicago to Winona on Wanderu at least 29 days ahead of time, you can save about HRK 230.96 on your ticket. Waiting until the last minute means missing out on these savings!

Which train should you take from Chicago to Winona?

There are 3 train lines with service from Chicago to Winona. Amtrak Empire Builder is your best bet, with 2 scheduled trains per day.

TrainDaily TripsAvg. TimeAvg. Price
Amtrak29h 18mHRK 464.01

Amtrak Borealis

15h 35mHRK 395.13
Amtrak Empire Builder25h 30mHRK 427.74

  • 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 2 Amtrak trains from Chicago to Winona every day, as well as 1 trips on the weekends, with prices starting from HRK 316.

  • Amtrak Borealis train tickets from Chicago to Winona start from HRK 227, and on average cost . Daily there are 1 Amtrak Borealis schedules to Winona. Amtrak Borealis in Chicago leaves from Union Station . And in Winona trains arrive at 65 E Mark St .

    From Chicago to Winona train travel on Amtrak Borealis takes 5 hours and 35 minutes. If you are looking to get to Winona faster, Amtrak Borealis offers more express schedule options with a travel time of 5 hours and 29 minutes.

    If you are looking to travel to Winona on a weekend there is typically one Amtrak Borealis scheduled trip per day, which will cost for a one-way weekend reservation from Chicago.

  • 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 Chicago to Winona

The distance between Chicago and Winona is approximately 253 miles, or 408 kilometers. The average train journey between these two cities takes 6 hours and 53 minutes, although the absolute fastest you could get there is 5 hours and 29 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.

Saturday tends to be the busiest day of the week with travelers taking trains from Chicago to Winona. Ticket price also tend to be more expensive on Saturday than other days. If you are hoping to have more room on the train and even save some change check out travel options on Monday instead, as less people travel then and deals are more likely to be found.

The earliest train departs Chicago at 6:00am while the last train of the day leaves at 3:00pm. 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 5 scheduled trains on most days. 3 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 Chicago.

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 is the train station in Chicago?

Chicago, IL - Union Station - CHIUST-0

Image credit: Jeramey Jannene

Link to image attribution

Main departure 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

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

Get around town with Moovit

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