Chicago, IL to Winona, MN train with Amtrak

Fri, Jun 05
+ Add return
Amtrak
Regionale
Deutsche Bahn
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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 Chicago, IL to Winona, MN

Showing times and prices for Jun 05

Cheapest price

$49

Average price

$70

Fastest journey

5 h 29 m

Average duration

5 h 29 m

Trains per day

2

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 $70 if you buy it on the day, but the cheapest tickets can be found for only $49.

Fast trains

Of the 2 trains that leave Chicago, IL for Winona, MN on Fri, Jun 05, 2 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.

On Fri, Jun 05 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 Fri, Jun 05 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.

  • Amtrak
    8:05 PM5h29
    Chicago, IL
    1:34 AMWinona, MN
    $491One-way
    0 transfers
  • Amtrak
    9:05 PM5h29
    Chicago, IL
    2:34 AMWinona, MN
    $901One-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 bus with prices starting from $115. For those with little time consider booking a flight which can get you there in 1h 21m. The ticket price range depends on the travel mode: a bus costs an average of $115, and a flight costs an average of $373.

Distance: 252 miles (406 km)

Compare train with

Most popular
Train
Flight
Bus
Driving

$162

Average price

$430

Average price

$118

Average price

Cheapest

$67

Average price

(fuel + tolls)

6h 1m

Average total duration

5h 31m

Onboard

+

30m

Additional time*

4h 21m

Average total duration

Fastest

1h 21m

Onboard

+

3h 0m

Additional time*

7h 53m

Average total duration

7h 23m

Onboard

+

30m

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 bus with an average price of $118 (€96).

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

A bus is $44 (€36) less than a train for this route with tickets for a train from Chicago, IL to Winona, MN costing on average $162 (€131).

A bus is $312 (€252) less than a flight for this route with tickets for a flight from Chicago, IL to Winona, MN costing on average $430 (€347).

The fastest way to travel from Chicago, IL to Winona, MN is by flight with an average journey time of 1h 21m.

Other travel options to Winona, MN take longer:

Train takes on average 5h 31m.

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 3m sooner (5h 31m by train vs 5h 34m by car). Tickets start at around $162 (€131) compared to roughly $67 (€54) 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, Thursday, June 4. You can also manually refresh the results below to see updated train journeys.

Last updated at
ProviderDepartsDurationArrivesTransfers
Tickets
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.

Fri
Jun 05
Sat
Jun 06
Sun
Jun 07
Mon
Jun 08
Tue
Jun 09
Wed
Jun 10
Thu
Jun 11

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 31m. Cheap train tickets for this journey start at $39 (€32) 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 31m
Cheapest ticket price
$39 (€32)
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
Fri
High Season
Jan - Mar
Low Season
Jul - Sep
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 $39 (€32). 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 Duration
5h 29m
Cheapest Price
$39 (€32)
Amtrak frequency
4 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 $39 (€32), while the average price is around $162 (€131).
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 $39 (€32).
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

Chicago
Winona
The major train station for departures in Chicago is Union Station. Find all the information you need to know about services, amenities and connections at Union Station for your trip from Chicago to Winona.
Amenities at train station
WifiWifi
LockersLockers
ParkingParking
DiningDining
ATMATM
TaxisTaxis
AccessibilityAccessibility
WCWC
HotelHotel
LoungeLounge
Lost and Found OfficeLost and Found Office
Ticket OfficeTicket Office
Bike ParkingBike Parking
Car RentalCar Rental
Information DeskInformation Desk
Luggage CartsLuggage Carts
information
phone
Phone Number
ticketOfficeHours
Ticket Office Hours
  • 5:00 AM - 12:00 AM Monday - Sunday
ticketOfficeHours
Distance to city center
3 km
platformCount
Number of platforms
24
Wifi
Wifi
  • Free
Parking
Parking
  • The car park is open 7 days a week from 5:00 a.m. to 12:00 a.m. Departures can be made outside of opening hours. Access via Canal Street.
Dining
Dining
  • The Chicago Firehouse Restaurant
  • Lou Mitchell's
Taxis
Taxis
  • Outside the main entrance.
Accessibility
Accessibility
  • Elevators, ramps, restrooms.
WC
WC
  • $1
Hotel
Hotel
  • The Kimpton Gray Hotel
  • JW Marriott Chicago
  • W Chicago - City Center
Lounge
Lounge
  • Located in the main hall
Lost and Found Office
Lost and Found Office
  • Located in the main hall
Car Rental
Car Rental
  • Avis
  • Budget
  • Enterprise
Information Desk
Information Desk
  • Located in the main hall
Luggage Carts
Luggage Carts
  • Free
Station Plan
  • Hall 1: main entrance, Amtrak services
  • Hall 2: Metra services
  • Hall 3: food court and retail shops
Public transit options for Union Station
  • Bus: Several lines available
  • CTA: Blue Line, Pink Line

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

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