- Must visit
Art Institute Of Chicago
One of the premier art museums in the US, known for Impressionist masterpieces, modern works, and the iconic bronze lions at its entrance.
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The cheapest and fastest trains from Winona, MN to Chicago, IL
Showing times and prices for Jun 22
Cheapest price
$40
Average price
$111
Fastest journey
5 h 34 m
Average duration
5 h 40 m
Trains per day
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
Of the 5 trains that leave Winona, MN for Chicago, IL on Mon, Jun 22, 5 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Mon, Jun 22 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, Jun 22 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 prices starting from $39. For those with little time consider booking a flight which can get you there in 1h 31m. The ticket price range depends on the travel mode: a train costs an average of $39, and a flight costs an average of $249.
Distance: 252 miles (406 km)
Compare train with
Most popular Train | Bus | Flight | Driving |
|---|---|---|---|
$85 Average price Cheapest | $114 Average price | $414 Average price | $66 Average price (fuel + tolls) |
6h 10m Average total duration 5h 40m Onboard + 30m Additional time* | 7h 50m Average total duration 7h 20m Onboard + 30m Additional time* | 4h 31m Average total duration Fastest 1h 31m Onboard + 3h 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 $85 (€70).
This is compared to other travel options from Winona, MN to Chicago, IL:
A train is $29 (€24) less than a bus for this route with tickets for a bus from Winona, MN to Chicago, IL costing on average $114 (€93).
A train is $329 (€269) 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 31m.
Other travel options to Chicago, IL take longer:
Train takes on average 5h 40m.
Bus takes on average 7h 20m.
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 $85 (€70) compared to roughly $66 (€54) in fuel and tolls — a saving of about $-19.18 (€-15.70). The journey takes 5h 40m 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, June 21. 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.
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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 40m. 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 34m.
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 40m |
Cheapest ticket price $39 (€32) |
Trains per day 5 |
Direct trains 3 |
Fastest train 5h 34m |
First train 6:10 AM |
Last train 3:05 PM |
Cheapest Month Mar |
Cheapest Day Sat |
High Season Oct - Dec |
Low Season Apr - Jun |
Busiest Day Tue |
Least Busy Day Mon |
Best time to book 21 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 Winona, MN to Chicago, IL trainsAmtrak trains will get you between Winona, MN and Chicago, IL 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 34m
Cheapest Price
$39 (€32)
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 Chicago
Things to do in Chicago
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
- Must visit
Field Museum
Major natural history museum famous for Sue the T. rex, ancient cultures, and extensive science collections that appeal to both adults and children.
- Must visit
Museum Of Science And Industry
Large hands-on science museum in Hyde Park featuring a submarine, space exhibits, engineering displays, and immersive family-friendly experiences.
- Must visit
Millennium Park
The city’s signature public space, home to Cloud Gate, gardens, events, and major skyline views that define modern Chicago.
- Must visit
The Magnificent Mile
Famous stretch of Michigan Avenue lined with historic buildings, shops, hotels, and frequent first-time visitor photo stops.
- Must visit
Chicago Riverwalk
Highly popular waterfront promenade with architecture views, bridges, and one of the best urban walks in the city.
Deep-Dish Pizza
Chicago’s iconic thick-crust pizza baked in a deep pan, layered with cheese, toppings, and chunky tomato sauce. It is one of the city’s most famous comfort foods.
Chicago-Style Hot Dog
An all-beef hot dog on a poppy seed bun topped with mustard, onions, neon relish, tomato, pickle spear, sport peppers, and celery salt. It is a classic local street food.
Italian Beef Sandwich
Thinly sliced roast beef piled onto an Italian roll, often dipped in seasoned jus and topped with sweet peppers or giardiniera. It is a defining Chicago sandwich.
Gene & Georgetti
A historic old-school steakhouse serving steaks, chops, and classic Italian-American dishes in a traditional setting.
Alinea
Chicago’s internationally acclaimed fine-dining restaurant known for highly inventive tasting menus and exceptional service.
Lou Malnati's Pizzeria
A long-established Chicago favorite known for buttery deep-dish pizza and a casual, family-friendly atmosphere.
United States Dollar
Moderate for a major U.S. city: casual food is manageable, but hotels, attractions, and downtown dining can be pricey.
Average meal costs
- Budget
- USD 10-18 for fast food or casual takeout.
- Mid-range
- USD 20-40 per person at a mid-range restaurant.
- Fine dining
- USD 75+ per person before drinks and tax.
- Coffee
- USD 4-7 for a regular café coffee.
Tipping culture
Tip 18-20% in restaurants; 20%+ for great service. Tip bartenders USD 1-2 per drink, taxis about 10-15%, and hotel staff a few dollars.
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 $39 (€32), while the average price is around $85 (€70).
The train from Winona, MN to Chicago, IL takes 5h 34m and runs 5 per day.
The first train from Winona, MN to Chicago, IL leaves at 6:10 AM.
The distance by train from Winona, MN to Chicago, IL is 252 miles (406 km).
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 $39 (€32).
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 34m 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
Winona
Chicago
The major train station for departures in Winona is Winona Station. Find all the information you need to know about services, amenities and connections at Winona Station for your trip from Winona to Chicago.
Winona Station
Amenities at train station
ParkingDiningTaxisAccessibilityWCHotelTicket Officeinformation
Number of platforms
1Parking
- Parking is available near the station
Taxis
- Outside the station
Accessibility
- Ramps, restrooms
Hotel
- Holiday Inn Express & Suites Winona
- AmericInn by Wyndham Winona
- Fairfield Inn & Suites by Marriott Winona
Station Plan
- The station consists of a single platform with shelter.
Public transit options for Winona Station
- Bus: Local bus services available
- Taxi: Local taxi services available
The major train station for arrivals in Chicago is Union Station. Find all the information you need to know about services, amenities and connections at Union Station for your journey to Chicago from Winona.
Amenities at train station
Wifi
LockersParkingDining
ATMTaxisAccessibilityWCHotel
Lounge
Lost and Found OfficeTicket Office
Bike Parking
Car Rental
Information Desk
Luggage Cartsinformation
Ticket Office Hours
- 5:00 AM - 12:00 AM Monday - Sunday
Distance to city center
3 kmNumber of platforms
24Wifi
- Free
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
- The Chicago Firehouse Restaurant
- Lou Mitchell's
Taxis
- Outside the main entrance
Accessibility
- Elevators, ramps, restrooms
WC
- $1
Hotel
- The Kimpton Gray Hotel
- JW Marriott Chicago
- W Chicago - City Center
Lounge
- Located in the main hall
Lost and Found Office
- Located in the main hall
Car Rental
- Avis
- Budget
- Enterprise
Information Desk
- Located in the main hall
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
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
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