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Winona to Chicago train

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Winona - Chicago Train Schedule

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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 25 minutes, but the fastest Amtrak train can make the trip in 5 hours and 34 minutes.

Distance253 mi (408 km)
Fastest train5h 34m
Lowest price$36.00
Trains per day3
Most frequent serviceAmtrak
Train lines2

Train Trip Reviews from Wanderu Customers

Average score for trains from Winona to Chicago

(Based on 5 ratings and reviews)

4.6

5.0

Pavel

December 15, 2021- Solo travel

Amtrak Empire Builder

Pros: arriving to final destination earlier than expected. Cons: Wifi in the train. Tips: buy tickets earlier than day before ride.

5.0

Dallas

December 5, 2019- Vacation

Amtrak Empire Builder

Pros: Easy way to travel, no stress. Cons: Nothing for us. Tips: Just sit back and enjoy.

4.0

Annmarie

June 23, 2019- Visiting family

Amtrak Empire Builder

Pros: The seats were comfortable. There was a toilet very close by which was helpful as i had a cane and walking between trains would have been too difficult. Smooth stops. Cons: making sure people get help to get off at their stops. Everyone should be able to get off before anyone else gets boards the train. This one girl had 3 bags and no one helped her get them down from the luggage areas and they kept letting people get on before she was able to get off. She would have been left behind if i hadn't asked people to please let her through, then another gentleman also asked the people to step aside. No Amtrak staff anywhere around. Tips: Bring a sweater or blanket, it can get rather cold on board.

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

The average price for a train ticket from Winona to Chicago is $56.60, By booking your trip at least 20 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 $56.68 more.

Monthly avg. prices

$125$100$75$50$25ONDJFMAMJJAS
Mark your calendar for February if you want to score the cheapest train tickets from Winona to Chicago. You’ll find the best deals during this time of year, when tickets cost an average of $71. If you're planning a trip from Winona to Chicago during August, bear in mind that ticket prices are usually higher during this month. Expect to pay about $113 for your train ticket, unless you book well in advance and find an even better deal.

Prices as travel date approaches

$125$100$75$50$253020100

Planning ahead pays off when it comes to booking your train trip from Winona to Chicago. By reserving your ticket on Wanderu at least 20 days before departure, you can save around $56.68. Don't miss out on these savings — book in advance!

Which train should you take from Winona to Chicago?

2 train services operate from Winona to Chicago. Amtrak usually has more trains scheduled, with 3 trips per day. That said, it's still worth comparing the prices and trip durations:

TrainDaily TripsAvg. TimeAvg. Price
Amtrak36h 56m$90.71
Amtrak Empire Builder25h 44m$107.30

  • 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 $36.

  • 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

Yes, there are trains that can take you the entire way from Winona to Chicago. However, there are also some trips on this route that require you to board another vehicle, such as a bus or a shuttle, during your journey. This is worth paying attention to as you book your trip, since a direct train may be preferable for its speed and convenience.

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 25 minutes, although the absolute fastest you could get there is 5 hours and 34 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.

On a weekly basis, the greatest number of passengers tend to travel by trains from Winona to Chicago on Saturday. Tickets for Saturday tend to also be the most expensive. For savvy travelers looking for cheaper priced tickets search for travel departing on Wednesday. Wednesday also tend to have less passengers which may make boarding faster and let you snag your perfect seat.

The earliest train departs Winona at 11:00am while the last train of the day leaves at 1:00pm. 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 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.

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 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 is the train station in Chicago?

Chicago, IL - Union Station - CHIUST-0

Image credit: Jeramey Jannene

Link to image attribution

Main arrival station: Chicago (Union Station), Illinois

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:

  • Chicago (Union Station), Illinois

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