- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
2,000+ travel companies
2,000+ travel companies
Scan to get our free app
Use our app to get live travel updates and book mobile tickets for trains, buses, flights, and ferries.
App Store
4.942K ratings
Google Play
4.6136K reviews
The cheapest and fastest trains from Winona, MN to Chicago, IL
Showing times, prices and bookable tickets for Sep 21
Cheapest price on Sep 21
$40
Average ticket price on Sep 21
$111
Fastest journey on Sep 21
5 h 34 m
Average journey duration on Sep 21
5 h 40 m
Trains on Sep 21
5
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 $111 if you buy it on the day, but the cheapest tickets can be found for only $40.
Fast trains
On Mon, Sep 21, we found 5 trains from Winona, MN to Chicago, IL, including 5 direct services.
On Mon, Sep 21 the direct trains cover the 406 km distance in an average of 5 h 40 m but if you time it right, some trains will get you there in just 5 h 34 m .
On Mon, Sep 21 the slowest trains will take 5 h 44 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.
7:40 PM5h34Winona, MN1:14 AMChicago, IL$401One-way0 transfers- 6:41 PM5h40Winona, MN12:21 AMChicago, IL$411One-way0 transfers
- 7:41 PM5h40Winona, MN1:21 AMChicago, IL$591One-way0 transfers
- 5:01 PM5h44Winona, MN10:45 PMChicago, IL$1421One-way0 transfers
- 4:01 PM5h44Winona, MN9:45 PMChicago, IL$2751One-way0 transfers
- 7:40 PM5h34Winona, MN1:14 AMChicago, IL$401One-way0 transfers
- 7:41 PM5h40Winona, MN1:21 AMChicago, IL$591One-way0 transfers
- 6:41 PM5h40Winona, MN12:21 AMChicago, IL$411One-way0 transfers
- 5:01 PM5h44Winona, MN10:45 PMChicago, IL$1421One-way0 transfers
- 4:01 PM5h44Winona, MN9:45 PMChicago, IL$2751One-way0 transfers
Travel Information
Compare train, bus, and flight for Winona, MN to Chicago, IL
Omio recommends booking the train as it is the most popular option from Winona, MN to Chicago, IL among Omio's users. If you are prioritising price, take the train, with an average ticket price of $161 For those with little time, consider booking a flight, which has an average total journey time of 3h 44m. Average ticket prices depend on the travel mode: a train costs an average of $161, while a flight costs an average of $414.
Distance: 252 miles (406 km)
Compare train with
Most popular Train | Bus | Flight | Driving |
|---|---|---|---|
$161 Average price Cheapest | $414 Average price | $67 Average price (fuel + tolls) | |
6h 7m Average total duration 5h 37m Onboard + 30m Additional time* | 3h 44m Average total duration Fastest 1h 44m Onboard + 2h 0m Additional time* | 4h 29m Average total duration (door-to-door) | |
Direct Options | Direct Options | Direct Options | Direct Options |
The cheapest way to travel from Winona, MN to Chicago, IL is a train with an average price of $161 (€131).
This is compared to other travel options from Winona, MN to Chicago, IL:
A train is $254 (€208) less than a flight for this route with tickets for a flight from Winona, MN to Chicago, IL costing on average $414 (€339).
The fastest way to travel from Winona, MN to Chicago, IL is by flight with an average journey time of 1h 44m.
Other travel options to Chicago, IL take longer:
Train takes on average 5h 37m.
It's helpful to compare your options as there are 3 ways to travel between Winona, MN and Chicago, IL including taking a train, bus, and flight.
We recommend using the train as it is the most popular way to get from Winona, MN to Chicago, IL among Omio's users.
Take the train. It's the cheaper option, and the extra time on board is usually more relaxing than driving it.
Tickets start at around $161 (€131) compared to roughly $67 (€55) in fuel and tolls — a saving of about $-93.42 (€-76.42). The journey takes 5h 37m versus 4h 29m by car, so you'll arrive a bit later, but you can work, read, or sleep along the way rather than spending the time behind the wheel. You'll also save the hassle of parking at the other end.
Driving is worth it if you're on a tight schedule, travelling as a group, or want to stop somewhere en route.
Live departures
Winona, MN to Chicago, IL train times
The table below shows live departures for Winona, MN to Chicago, IL trains for today, Sunday, September 20. You can also manually refresh the results below to see updated train journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 4:01 PM Winona, MN | 5h44 | 9:45 PM Chicago, IL | 0 transfersDirect | |
| 6:41 PM Winona, MN | 5h40 | 12:21 AM Chicago, IL | 0 transfersDirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Winona, MN to Chicago, IL 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.
Mon
Sep 21
Sep 21
Tue
Sep 22
Sep 22
Wed
Sep 23
Sep 23
Thu
Sep 24
Sep 24
Fri
Sep 25
Sep 25
Sat
Sep 26
Sep 26
Sun
Sep 27
Sep 27
Journey information
Overview: Train from Winona, MN to Chicago, IL
USAUSA
Trains from Winona, MN to Chicago, IL run on average 5 times per day, taking around 5h 37m. Cheap train tickets for this journey start at $41 (€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
Distance 252 miles (406 km) |
Average train duration 5h 37m |
Cheapest ticket price $41 (€34) |
Trains per day 5 |
Direct trains 3 |
Fastest train 5h 25m |
First train 6:10 AM |
Last train 3:05 PM |
Cheapest Month Mar |
Cheapest Day Sun |
High Season Oct - Dec |
Low Season Apr - Jun |
Busiest Day Mon |
Least Busy Day Thu |
Best time to book 1 day |
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 Winona, MN to Chicago, IL trainsAmtrak trains will get you between Winona, MN and Chicago, IL from $41 (€34). 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
$41 (€34)
Amtrak frequency
6 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 $26 fee. Must be in carrier. Service animals travel free
Quiet zone
Complete guide to Chicago, IL
Things to do in Chicago, IL
Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
- Must visit
Field Museum
Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.
- Must visit
Museum of Science and Industry
Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.
- Must visit
Millennium Park
Lively lakefront park with Cloud Gate, Crown Fountain, gardens, and major public art in central Chicago.
- Must visit
Magnificent Mile
Famous shopping boulevard lined with architecture, hotels, riverfront views, and major city energy.
- Must visit
Chicago Riverwalk
Scenic pedestrian-friendly riverwalk with boat docks, public art, bridges, and standout skyline perspectives.
Deep-Dish Pizza
Deep-dish pizza is Chicago’s iconic pie with a tall buttery crust, layers of cheese and toppings, and chunky tomato sauce baked on top.
Chicago-Style Hot Dog
The Chicago-style hot dog is an all-beef frank on a poppy seed bun with mustard, relish, onion, tomato, pickle, peppers, and celery salt.
Italian Beef Sandwich
Italian beef is thin-sliced roast beef piled onto a roll, often dipped in savory juices and topped with sweet peppers or spicy giardiniera.
Johnnie's Beef
Classic spot for juicy Italian beef sandwiches, especially dipped and topped with spicy giardiniera, with a casual local feel.
Superdawg Drive-In
Legendary stand for Chicago-style hot dogs and char-grilled sausages, served fast in a no-frills local landmark.
Alinea
World-famous fine dining destination offering a highly creative tasting menu and refined service in an elegant setting.
US dollar ($)
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.
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.
Train ticket prices from Winona, MN to Chicago, IL can vary. The cheapest ticket starts at $41 (€34), while the average price is around $161 (€131).
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.
There is no high speed train available from Winona, MN to Chicago, IL.
Yes, there is a direct train from Winona, MN to Chicago, IL. This service operates 3 times per day, provided by Amtrak.
Unfortunately, there is no night train available from Winona, MN to Chicago, IL.
The train station in Winona, MN that goes to Chicago, IL is Winona Station, Winona, MN, which connects to Chicago Union Station, Chicago, IL.
The cheapest way to get from Winona, MN to Chicago, IL is by train, with a cost of around $41 (€34).
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.
A day trip from Winona, MN to Chicago, IL is not feasible, as the travel time is 5h 25m and the journey covers 252 miles (406 km). However, there are 5 train trips available per day.
In Chicago, IL, you can explore the Museum of Science and Industry and its interactive exhibits, enjoy the vibrant neighborhoods like Wicker Park and Lincoln Park, take a river cruise to view iconic architecture, and attend a live performance at the historic Chicago Theatre. Visit Lincoln Park Zoo for a free and enjoyable day. For sights, don't miss Millennium Park with its modern art, the renowned Art Institute of Chicago, the entertainment hub of Navy Pier, panoramic views from Willis Tower Skydeck, and the fascinating exhibits at the Field Museum.
To fully experience Chicago, IL, plan for at least 3-4 days to visit key attractions such as Millennium Park, The Art Institute of Chicago, Navy Pier, and explore diverse neighborhoods.
Yes, you can take the train from Winona, MN to Chicago, IL.
Since neither Winona, MN nor Chicago, IL 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 Chicago, IL include Milwaukee, WI, South Bend, IN, New Buffalo, MI, Racine, WI, Elkhart, IN.
We recommend using the train as it is the most popular way to get from Winona, MN to Chicago, IL 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 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.
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+1 800-872-7245
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.
Which Chicago, IL station do trains from Winona, MN arrive at?
Trains from Winona, MN to Chicago, IL arrive at Union Station. Union Station is 1 miles (3 km) from Chicago, IL city centre.
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.
Most popular train connections from Winona, MN
More options for your journey from Winona, MN to Chicago, IL
Here are some other resources that might have the information you need
Most popular trains to and from Chicago, IL and Winona, MN
Most popular train connections to Chicago, IL
The Omio App Makes Travel Planning Easy
We’ll get you where you want to go. From live train updates to mobile tickets, our innovative app is the ideal way to plan and keep track of your travel.
