Winona, MN to Chicago, IL train with Amtrak

Thu, Nov 05
+ Add return
Amtrak
Regionale
Deutsche Bahn
iryo
Frecciarossa
2,000+ travel companies
Amtrak
Regionale
Deutsche Bahn
iryo
Frecciarossa
2,000+ travel companies
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The cheapest and fastest trains from Winona, MN to Chicago, IL

Showing times, prices and bookable tickets for Nov 05
Cheapest price on Nov 05
€34
Average ticket price on Nov 05
€89
Fastest journey on Nov 05
5 h 40 m
Average journey duration on Nov 05
7 h 27 m
Trains on Nov 05
3
Distance
406 km
Cheap tickets

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

The average ticket from Winona, MN to Chicago, IL will cost around €89 if you buy it on the day, but the cheapest tickets can be found for only €34.

Fast trains

On Thu, Nov 05, we found 3 trains from Winona, MN to Chicago, IL, including 3 direct services.

On Thu, Nov 05 the direct trains cover the 406 km distance in an average of 7 h 27 m but if you time it right, some trains will get you there in just 5 h 40 m .

On Thu, Nov 05 the slowest trains will take 8 h 20 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
    0 transfers
  • Amtrak
    0 transfers
  • Amtrak
    0 transfers

Journey information

Overview: Train from Winona, MN to Chicago, IL

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Trains from Winona, MN to Chicago, IL run on average 5 times per day, taking around 5h 38m. Cheap train tickets for this journey start at €34 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 25m.

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

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Journey facts

  • Distance252 miles (406 km)
  • Average train duration5h 38m
  • Cheapest ticket price€34
  • Trains per day5
  • Direct trains3
  • Fastest train5h 25m
  • First train6:10 AM
  • Last train3:05 PM
  • Cheapest MonthMar
  • Cheapest DayWed
  • High SeasonOct - Dec
  • Low SeasonApr - Jun
  • Busiest DayMon
  • Least Busy DayThu
  • Best time to book1 day

Understand & plan this route

Explore this journey

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  • Why book with Omio?Compare options, payment & support
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

Frequently asked questions about your Winona, MN to Chicago, IL trip

Use these quick route answers to check fares, travel time, departure options, and direct services before booking from Winona, MN to Chicago, IL.

Train ticket prices from Winona, MN to Chicago, IL can vary. The cheapest ticket starts at €34, while the average price is around €130.
The train from Winona, MN to Chicago, IL takes 5h 25m and runs 5 per day.
The distance by train from Winona, MN to Chicago, IL is 252 miles (406 km).
The first train from Winona, MN to Chicago, IL leaves at 6:10 AM.
The last train from Winona, MN to Chicago, IL leaves at 3:05 PM.
Yes, there is a direct train from Winona, MN to Chicago, IL. This service operates 3 times per day, provided by Amtrak.

Live departures

Winona, MN to Chicago, IL train times

The table below shows live departures for Winona, MN to Chicago, IL trains for today, Wednesday, November 4. You can also manually refresh the results below to see updated train journeys.

Last updated at
ProviderDepartsDurationArrivesTransfers
Tickets
Amtrak28 Empire Builder · 383 Illinois Zephyr11:01 AM Winona Station, Winona, MN
7h12
6:13 PM LaGrange Road Station, La Grange, IL1 transfer
Amtrak28 Empire Builder · 307 Lincoln Service11:01 AM Winona Station, Winona, MN
8h31
7:32 PM Summit Station, Summit, IL1 transfer
Amtrak8 Empire Builder · 307 Lincoln Service11:01 AM Winona Station, Winona, MN
8h31
7:32 PM Summit Station, Summit, IL1 transfer

This is the last train of the day.

Find all the dates and times for this journey

Train companies

Train companies from Winona, MN to Chicago, IL

Trains from Winona, MN to Chicago, IL with Amtrak. Night trains available on this route with Amtrak. High-speed trains available on this route with Amtrak. Use the details below to compare onboard facilities.

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 25m
Cheapest Amtrak Price
€34
Amtrak frequency
5 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

Companies, tickets, and onboard amenities between Winona, MN and Chicago, IL

Review the details behind your booking, from operators and ticket rules to luggage, onboard amenities, accessibility, and route-specific travel policies.

Yes, there is a high-speed train from Winona, MN to Chicago, IL.
Yes, there is a night train from Winona, MN to Chicago, IL.
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.

Complete guide to Chicago, IL

Things to do in Chicago, IL

Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.

  • Must visit

Art Institute of Chicago

World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.

  • Must visit

Field Museum

Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.

  • Must visit

Museum of Science and Industry

Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.

US dollar ($)

Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.

Average meal costs

Budget
$10-18 for fast food or casual takeout.
Mid-range
$20-40 per person for a restaurant meal.
Fine dining
$75+ per person for upscale restaurants.
Coffee
$3-6 for coffee or cappuccino.

Tipping culture

Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.

Plan your visit to Chicago, IL

Get destination-focused answers for the end of your trip, including what to do, when to go, practical entry details, and tips for making the most of your time in Chicago, IL.

The train journey from Winona, MN to Chicago, IL offers scenic views of the Mississippi River, picturesque river bluffs, and glimpses of Midwestern landscapes, particularly during the first half of the trip.
Popular day trips by train from Chicago, IL include Milwaukee, WI, South Bend, IN, New Buffalo, MI, Racine, WI, Elkhart, IN.
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 Chicago, IL, travelers should be cautious of pickpocketing and purse snatching, especially in crowded areas like public transit and popular tourist spots. Common scams include fake charity solicitations and distraction thefts. It is advisable to stay alert in neighborhoods outside downtown after dark and use authorized transportation services to avoid unlicensed taxi scams. Keeping valuables secure and being aware of surroundings helps mitigate these risks.
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.

FAQs: Trains from Winona, MN to Chicago, IL

Find answers to the most common questions about traveling from Winona, MN to Chicago, IL 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 Chicago, IL, this guide helps you travel smarter and with confidence.

FAQs
Yes, you can take the train from Winona, MN to Chicago, IL.

popular train stations

Popular train stations from Winona, MN to Chicago, IL

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

Departure train stations in Winona
Arrival train stations in Chicago

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

Trains from Winona, MN to Chicago, IL leave from Winona Station. The station is 0 miles (1 km) from Winona, MN city centre at 65 East Mark Street, Winona, MN 55987, USA.
Winona Station65 East Mark Street, Winona, MN 55987, USA+1 800-872-7245ParkingDiningTaxisAccessibilityWCHotelTicket Office
City-centre transport

Getting to Winona Station from Winona city centre

BusLocal bus services available
TaxiLocal taxi services available

Winona Station train station facilities and services

Winona Station has practical services for this route, including Parking, Dining, Taxis, Accessibility, WC, Hotel, and Ticket Office.

Food and drink

Food and drink options are available at Winona Station.

Tickets and information

Ticket office support is available at Winona Station.

Parking, taxis and toilets

Available at Winona Station: Parking, Taxis, WC.

Accessibility

Accessibility facilities are available at Winona Station: Ramps, restrooms.

Shops, hotels and contact

Nearby hotels include Holiday Inn Express & Suites Winona, AmericInn by Wyndham Winona, Fairfield Inn & Suites by Marriott Winona.

Train stations for Winona, MN to Chicago, IL

Check train stations information for Winona, MN and Chicago, IL, including where trains depart and arrive on this route.

The train station in Winona, MN that goes to Chicago, IL is Winona Station, which connects to Union Station.

Most popular train connections from Winona, MN

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