- Must visit
Minnesota Marine Art Museum
Regional art museum with American art, changing exhibitions, and a strong local connection. A key cultural stop in Winona.
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The cheapest and fastest trains from Chicago, IL to Winona, MN
Showing times, prices and bookable tickets for Oct 21
Cheapest price on Oct 21
$565
Average ticket price on Oct 21
$565
Fastest journey on Oct 21
5 h 29 m
Average journey duration on Oct 21
5 h 29 m
Trains on Oct 21
1
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 $565 if you buy it on the day, but the cheapest tickets can be found for only $565.
Fast trains
On Wed, Oct 21, we found 1 trains from Chicago, IL to Winona, MN, including 1 direct services.
On Wed, Oct 21 the direct trains cover the 406 km distance in an average of 5 h 29 m but if you time it right, some trains will get you there in just 5 h 29 m .
On Wed, Oct 21 the slowest trains will take 5 h 29 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.
8:05 PM5h29Chicago, IL1:34 AMWinona, MN$5651One-way0 transfers
- 8:05 PM5h29Chicago, IL1:34 AMWinona, MN$5651One-way0 transfers
Journey information
Overview: Train from Chicago, IL to Winona, MN
USAUSA
Trains from Chicago, IL to Winona, MN run on average 3 times per day, taking around 5h 29m. Cheap train tickets for this journey start at $75 if you book in advance.
There are 2 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
Distance 252 miles (406 km) |
Average train duration 5h 29m |
Cheapest ticket price $75 |
Trains per day 3 |
Direct trains 2 |
Fastest train 5h 25m |
First train 6:10 AM |
Last train 3:05 PM |
Cheapest Month Sep |
Cheapest Day Thu |
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
Live departures
Chicago, IL to Winona, MN train times
The table below shows live departures for Chicago, IL to Winona, MN trains for today, Tuesday, October 20. You can also manually refresh the results below to see updated train journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 329 Hiawatha Service · 1333 Borealis | 6:10 AM Chicago Union Station, Chicago, IL | 10h35 | 4:45 PM Winona Station, Winona, MN | 1 transfer | |
| 331 Hiawatha Service · 1333 Borealis | 8:25 AM Chicago Union Station, Chicago, IL | 8h20 | 4:45 PM Winona Station, Winona, MN | 1 transfer | |
| 1333 Borealis | 11:10 AM Chicago Union Station, Chicago, IL | 5h35 | 4:45 PM Winona Station, Winona, MN | 0 transfersDirect | |
| 27 Empire Builder | 3:05 PM Chicago Union Station, Chicago, IL | 5h29 | 8:34 PM Winona Station, Winona, MN | 0 transfersDirect | |
| 7 Empire Builder | 3:05 PM Chicago Union Station, Chicago, IL | 5h29 | 8:34 PM Winona Station, Winona, MN | 0 transfersDirect |
Find all the dates and times for this journey
Train companies: Amtrak from Chicago, IL to Winona, MN trainsAmtrak trains will get you between Chicago, IL and Winona, MN from $75. 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 25m
Cheapest Amtrak Price
$75
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 $26 fee. Must be in carrier. Service animals travel free
Quiet zone
Complete guide to Winona, MN
Things to do in Winona, MN
Discover the best of Winona, MN — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Winona, MN trip today.
- Recommended
Winona County History Center
County history museum in a grand former home, featuring exhibits on Winona life, industry, and people. Good for local context.
Polk Museum
University museum with geology, natural history, and cultural exhibits. A useful stop for families and visitors exploring campus.
- Must visit
Garvin Heights City Park
Blufftop park and viewpoint with sweeping views over Winona, the Mississippi, and surrounding bluffs. A classic first stop in the city.
- Must visit
Sugar Loaf
Prominent bluff trail area with a staircase climb and rewarding views over the river valley. A local favorite for active visitors.
- Recommended
Lake Park
Lakeside city park with walking paths, playgrounds, and water views near downtown. Popular for an easy stroll and relaxing scenery.
Tater Tot Hotdish
A hearty Midwestern hotdish baked with meat, vegetables, and a creamy base, reflecting Minnesota church suppers and family tables.
- Gluten-free
Walleye
Walleye from regional lakes, usually pan-fried or broiled. It is a classic Upper Midwest fish dish strongly tied to Minnesota dining.
Wild Rice Soup
A rich wild rice soup often made with cream, vegetables, and chicken. Wild rice is a signature Minnesota ingredient with deep regional roots.
Island City Brewing Company
Modern pizzeria and brewpub with house beers, wood-fired pizzas, and a lively social atmosphere near downtown.
Lakeview Drive Inn
Casual local favorite serving burgers, sandwiches, and bar food in a laid-back downtown setting popular with residents and visitors.
Bub's Brewing Company
Long-running German restaurant and tavern known for schnitzel, sausages, and old-school supper club atmosphere.
US Dollar ($)
Moderate for a small US city. Hotels and dining are usually cheaper than major US tourist hubs, while transport often requires a car or taxi.
Average meal costs
- Budget
- $10-15 for fast food or a simple meal.
- Mid-range
- $18-30 per person for a restaurant meal.
- Fine dining
- $40+ per person for upscale dining.
- Coffee
- $3-5 for a coffee drink.
Tipping culture
Tip 15-20% at restaurants, about 10% for taxis, and $1-2 at cafes for barista service or takeaway.
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.
Train ticket prices from Chicago, IL to Winona, MN can vary. The cheapest ticket starts at $75, while the average price is around $186.
The train from Chicago, IL to Winona, MN takes 5h 25m and runs 3 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 2 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 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.
Yes, you can take the train from Chicago, IL to Winona, MN.
Popular day trips by train from Winona, MN include Coon Rapids, MN, La Crosse, WI, Wisconsin Dells, WI.
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+1 800-872-7245
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 · $4 · 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.
Which Winona, MN station do trains from Chicago, IL arrive at?
Trains from Chicago, IL to Winona, MN arrive at Winona Station. Winona Station is 0 miles (1 km) from Winona, MN city centre.
Winona Station65 East Mark Street, Winona, MN 55987, USA+1 800-872-7245
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.
Most popular train connections from Chicago, IL
More options for your journey from Chicago, IL to Winona, MN
Here are some other resources that might have the information you need
Most popular trains to and from Winona, MN and Chicago, IL
Most popular train connections to Winona, MN
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