Chicago, IL to Winona, MN train with Amtrak

Sun, Sep 06
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Amtrak
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Deutsche Bahn
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2,000+ travel companies
Amtrak
Regionale
Deutsche Bahn
iryo
Frecciarossa
2,000+ travel companies
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The cheapest and fastest trains from Chicago, IL to Winona, MN

Showing times, prices and bookable tickets for Sep 06

Cheapest price on Sep 06

lei507

Average ticket price on Sep 06

lei916

Fastest journey on Sep 06

5 h 29 m

Average journey duration on Sep 06

5 h 31 m

Trains on Sep 06

3

Distance

406 km

Cheap tickets

The best way to find a cheap train ticket from Chicago, IL to Winona, MN is to book your journey as far in advance as possible and to avoid traveling at rush hour.

The average ticket from Chicago, IL to Winona, MN will cost around lei916 if you buy it on the day, but the cheapest tickets can be found for only lei507.

Fast trains

On Sun, Sep 06, we found 3 trains from Chicago, IL to Winona, MN, including 3 direct services.

On Sun, Sep 06 the direct trains cover the 406 km distance in an average of 5 h 31 m but if you time it right, some trains will get you there in just 5 h 29 m .

On Sun, Sep 06 the slowest trains will take 5 h 35 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.

  • Amtrak
    9:05 PM5h29
    Chicago, IL
    2:34 AMWinona, MN
    lei5071One-way
    0 transfers
  • Amtrak
    4:10 PM5h35
    Chicago, IL
    9:45 PMWinona, MN
    lei5431One-way
    0 transfers
  • Amtrak
    8:05 PM5h29
    Chicago, IL
    1:34 AMWinona, MN
    lei16971One-way
    0 transfers

Travel Information

Compare train, bus, and flight for Chicago, IL to Winona, MN

Omio recommends booking the train as it is the most popular option from Chicago, IL to Winona, MN among Omio's users. If you are prioritising price, take the train, with an average ticket price of lei414 For those with little time, consider booking a flight, which has an average total journey time of 3h 25m. Average ticket prices depend on the travel mode: a train costs an average of lei414, while a flight costs an average of lei1742.

Distance: 252 miles (406 km)

Compare train with

Most popular
Train
Bus
Flight
Driving

lei414

Average price

Cheapest

lei534

Average price

lei1742

Average price

lei307

Average price

(fuel + tolls)

6h 3m

Average total duration

5h 33m

Onboard

+

30m

Additional time*

7h 53m

Average total duration

7h 23m

Onboard

+

30m

Additional time*

3h 25m

Average total duration

Fastest

1h 25m

Onboard

+

2h 0m

Additional time*

5h 34m

Average total duration

(door-to-door)

Direct Options

Direct Options

Direct Options

Direct Options

The cheapest way to travel from Chicago, IL to Winona, MN is a train with an average price of lei414.

This is compared to other travel options from Chicago, IL to Winona, MN:

A train is lei120 less than a bus for this route with tickets for a bus from Chicago, IL to Winona, MN costing on average lei534.

A train is lei1328 less than a flight for this route with tickets for a flight from Chicago, IL to Winona, MN costing on average lei1742.

The fastest way to travel from Chicago, IL to Winona, MN is by flight with an average journey time of 1h 25m.

Other travel options to Winona, MN take longer:

Train takes on average 5h 33m.

Bus takes on average 7h 23m.

It's helpful to compare your options as there are 3 ways to travel between Chicago, IL and Winona, MN including taking a train, bus, and flight.
We recommend using the train as it is the most popular way to get from Chicago, IL to Winona, MN among Omio's users.
Take the train. It's meaningfully faster than driving, and the time saved usually justifies the price.

You'll arrive about 1m sooner (5h 33m by train vs 5h 34m by car). Tickets start at around lei414 compared to roughly lei307 in fuel and tolls — so you're paying a bit more, but getting hours of your day back, a city-centre arrival, and the freedom to work or relax instead of drive.

Direct services run with Amtrak.

Driving makes more sense if you're travelling as a group (where fuel costs split several ways), want to stop along the way, or need a car once you arrive.

Live departures

Chicago, IL to Winona, MN train times

The table below shows live departures for Chicago, IL to Winona, MN trains for today, Saturday, September 5. You can also manually refresh the results below to see updated train journeys.

Last updated at
ProviderDepartsDurationArrivesTransfers
Tickets
Amtrak5:10 PM Chicago, IL
5h35
10:45 PM Winona, MN0 transfersDirect
Amtrak8:05 PM Chicago, IL
5h29
1:34 AM Winona, MN0 transfersDirect
Amtrak9:05 PM Chicago, IL
5h29
2:34 AM Winona, MN0 transfersDirect

This is the last train of the day.

Find all the dates and times for this journey

Compare prices and tickets Chicago, IL to Winona, MN by train, bus, or flight

Compare train, bus, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.

Sun
Sep 06
Mon
Sep 07
Tue
Sep 08
Wed
Sep 09
Thu
Sep 10
Fri
Sep 11
Sat
Sep 12

Journey information

Overview: Train from Chicago, IL to Winona, MN

USAUSA
USAUSA
Icon of train

Trains from Chicago, IL to Winona, MN run on average 4 times per day, taking around 5h 33m. Cheap train tickets for this journey start at lei186 if you book in advance.

There are 3 trains per day. The earliest train runs at 06:10, the last at 15:05. The fastest train covers the 252 miles (406 km) distance in 5h 29m.

Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Distance
252 miles (406 km)
Average train duration
5h 33m
Cheapest ticket price
lei186
Trains per day
4
Direct trains
3
Fastest train
5h 29m
First train
6:10 AM
Last train
3:05 PM
Cheapest Month
Sep
Cheapest Day
Sat
High Season
Jan - Mar
Low Season
Jul - Sep
Busiest Day
Wed
Least Busy Day
Wed
Best time to book
49 days
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information

Train companies: Amtrak from Chicago, IL to Winona, MN trainsAmtrak trains will get you between Chicago, IL and Winona, MN from lei186. With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.

Amtrak

About
Amtrak is the main passenger train operator in the United States, providing medium- and long-distance intercity services across 46 states and three Canadian provinces. Operating over 300 trains daily and serving more than 500 destinations, Amtrak connects cities and regions nationwide through routes such as the high-speed Acela in the Northeast Corridor, the scenic Coast Starlight along the West Coast, and the Empire Builder linking Chicago to the Midwest and the Pacific Northwest. Other notable services include the Northeast Regional, Keystone Service, and the unique Auto Train, which allows passengers to bring their cars onboard. Amtrak offers a variety of classes to suit different budgets and travel needs, including Coach, Business, First Class, and Sleeper Class with options like Roomettes, Bedrooms, and Bedroom Suites for overnight journeys. Ticket types include Saver, Value, Flexible, Business, and Premium. Onboard amenities vary by service but may include comfortable seating, Wi-Fi, power outlets, dining options, and lounge access on select trains. Popular routes include Washington, D.C.–Boston, San Diego–San Luis Obispo, San Jose–Sacramento, and Chicago–Seattle.
Luggage & cancellation policy
Average Amtrak Duration
5h 29m
Cheapest Amtrak Price
lei186
Amtrak frequency
2 a day
Luggage included
2 personal items and 2 carry-on bags included free
Luggage storage
Overhead racks, under seats, and designated luggage areas at end of cars
Cancellation Policy
Cancellation policies depend on ticket type and timing
Refund
Full refund if train is canceled by Amtrak
Amenities on board the train
Wifi
Food sold onboard
Café car with snacks, beverages, and light meals. Long-distance trains have full-service dining cars
Seat reservation
Included in ticket price for Business and First Class. Optional fee for Coach Class
Toilets
USB plugs
Accessibility
Wheelchair spaces, accessible restrooms, Red Cap assistance service, accessible platforms and stations
Pets
Small pets under 20 pounds allowed for $26 fee. Must be in carrier. Service animals travel free
Quiet zone

FAQs: Trains from Chicago, IL to Winona, MN

Find answers to the most common questions about traveling from Chicago, IL to Winona, MN by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Winona, MN, this guide helps you travel smarter and with confidence.

FAQs
Train ticket prices from Chicago, IL to Winona, MN can vary. The cheapest ticket starts at lei186, while the average price is around lei414.
The train from Chicago, IL to Winona, MN takes 5h 29m and runs 4 per day.
The distance by train from Chicago, IL to Winona, MN is 252 miles (406 km).
The first train from Chicago, IL to Winona, MN leaves at 6:10 AM.
The last train from Chicago, IL to Winona, MN leaves at 3:05 PM.
There is no high speed train available from Chicago, IL to Winona, MN.
Yes, there is a direct train from Chicago, IL to Winona, MN. This service operates 3 times per day, provided by Amtrak.
Unfortunately, there is no night train available from Chicago, IL to Winona, MN.
The train station in Chicago, IL that goes to Winona, MN is Chicago Union Station, Chicago, IL, which connects to Winona Station, Winona, MN.
The cheapest way to get from Chicago, IL to Winona, MN is by train, with a cost of around lei186.
The train journey from Chicago, IL to Winona, MN offers scenic views, particularly as it travels along the Mississippi River, providing picturesque landscapes, especially during the fall when the foliage adds vibrant colors to the scenery.
A day trip from Chicago, IL to Winona, MN is not feasible as the journey takes 5h 29m each way and trains run 4 times per day. The distance is 252 miles (406 km).
To fully enjoy Winona, MN, including its cultural sites like the Minnesota Marine Art Museum, outdoor activities on the Mississippi River, and a hike up to Garvin Heights Lookout, plan for a 2 to 3-day stay.
Yes, you can take the train from Chicago, IL to Winona, MN.
Since neither Chicago, IL nor Winona, MN are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and United States. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
Popular day trips by train from Winona, MN include Coon Rapids, MN, La Crosse, WI, Wisconsin Dells, WI.
We recommend using the train as it is the most popular way to get from Chicago, IL to Winona, MN among Omio's users.
Items not allowed on trains typically include hazardous materials such as explosives, flammable liquids, corrosive substances, and illegal drugs. Additionally, large or bulky items that may obstruct aisles or emergency exits, as well as pets without proper carriers, may be restricted. Specific prohibited items can vary by train operator and region, so please check the rules for your particular journey.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Winona, MN, travelers should be aware of typical urban safety concerns such as petty theft and vehicle break-ins, especially in busy or tourist-heavy areas. It is advisable to keep personal belongings secure and avoid leaving valuables visible in parked cars. Additionally, travelers should be cautious of unofficial ticket sellers or offers that seem too good to be true when purchasing transportation or event tickets to avoid scams. Staying informed about local alerts and using reputable vendors can help ensure a safe visit.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.

popular train stations

Popular train stations from Chicago, IL to Winona, MN

Most Chicago, IL to Winona, MN trains use the Union Station to Winona Station station pair. Use this guide to compare Chicago, IL and Winona, MN train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.

Departure train stations in Chicago
Arrival train stations in Winona

Which Chicago, IL station do trains to Winona, MN leave from?

Trains from Chicago, IL to Winona, MN leave from Union Station. The station is 1 miles (3 km) from Chicago, IL city centre at 225 South Canal Street, Chicago, IL 60606, USA.
Union Station225 South Canal Street, Chicago, IL 60606, USA+1 800-872-7245WifiLockersParkingDiningATMTaxisAccessibilityWCHotelLoungeLost and Found OfficeTicket OfficeBike ParkingCar RentalInformation DeskLuggage Carts
City-centre transport

Getting to Union Station from Chicago city centre

Union Station is 3 km from Chicago city centre. Public transport options include:

Bus28, 151 · 7m · lei17 · every ~13 min

Union Station train station facilities and services

Union Station has practical services for this route, including Wifi, Lockers, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Lounge, Lost and Found Office, Ticket Office, Bike Parking, Car Rental, Information Desk, and Luggage Carts.

Food and drink

Food options include: The Chicago Firehouse Restaurant, Lou Mitchell's

Wi-Fi and ATMs

Free. ATMs are available in the train station.

Tickets and information

Ticket office support is available at Union Station. Information desks are located in the main hall.

Luggage and lost property

Luggage storage is available at Union Station. Lost and found is available at the station.

Parking, taxis and toilets

Available at Union Station: Parking, Taxis, WC.

Bike and car services

Available at Union Station: Bike Parking, Car Rental.

Accessibility

Accessibility facilities are available at Union Station: Elevators, ramps, restrooms.

Shops, hotels and contact

Nearby hotels include The Kimpton Gray Hotel, JW Marriott Chicago, W Chicago - City Center.

More options for your journey from Chicago, IL to Winona, MN

Here are some other resources that might have the information you need

HomeTrainsTrains in USAChicago, IL to Winona, MN train

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