The cheapest and fastest trains from Chicago Union Station, Chicago, IL to Winona Station, Winona, MN
- Cheapest price on Nov 03
- $39
- Average ticket price on Nov 03
- $218
- Fastest journey on Nov 03
- 5 h 29 m
- Average journey duration on Nov 03
- 5 h 32 m
- Trains on Nov 03
- 4
- Distance
- 405 km
The best way to find a cheap train ticket from Chicago Union Station, Chicago, IL to Winona Station, 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 Union Station, Chicago, IL to Winona Station, Winona, MN will cost around $218 if you buy it on the day, but the cheapest tickets can be found for only $39.
On Tue, Nov 03, we found 4 trains from Chicago Union Station, Chicago, IL to Winona Station, Winona, MN, including 4 direct services.
On Tue, Nov 03 the direct trains cover the 405 km distance in an average of 5 h 32 m but if you time it right, some trains will get you there in just 5 h 29 m .
On Tue, Nov 03 the slowest trains will take 5 h 35 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.

5:10 PM 5h35 Chicago Union Station, Chicago, IL 10:45 PM Winona Station, Winona, MN $39 1 One-way 0 transfers
4:10 PM 5h35 Chicago Union Station, Chicago, IL 9:45 PM Winona Station, Winona, MN $59 1 One-way 0 transfers
9:05 PM 5h29 Chicago Union Station, Chicago, IL 2:34 AM Winona Station, Winona, MN $88 1 One-way 0 transfers
8:05 PM 5h29 Chicago Union Station, Chicago, IL 1:34 AM Winona Station, Winona, MN $688 1 One-way 0 transfers

9:05 PM 5h29 Chicago Union Station, Chicago, IL 2:34 AM Winona Station, Winona, MN $88 1 One-way 0 transfers
8:05 PM 5h29 Chicago Union Station, Chicago, IL 1:34 AM Winona Station, Winona, MN $688 1 One-way 0 transfers
5:10 PM 5h35 Chicago Union Station, Chicago, IL 10:45 PM Winona Station, Winona, MN $39 1 One-way 0 transfers
4:10 PM 5h35 Chicago Union Station, Chicago, IL 9:45 PM Winona Station, Winona, MN $59 1 One-way 0 transfers
Journey information
Overview: Train from Chicago Union Station, Chicago, IL to Winona Station, Winona, MN
Trains from Chicago Union Station, Chicago, IL to Winona Station, Winona, MN run on average 4 times per day, taking around 5h 29m. Cheap train tickets for this journey start at $60 (€50) if you book in advance.
There are 3 trains per day. The earliest train runs at 13:25, the last at 20:05. The fastest train covers the 251 miles (405 km) distance in 5h 25m.
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Journey facts
- Distance251 miles (405 km)
- Average train duration5h 29m
- Cheapest ticket price$60 (€50)
- Trains per day4
- Direct trains3
- Fastest train5h 25m
- First train1:25 PM
- Last train8:05 PM
- Cheapest MonthDec
- Cheapest DayWed
- High SeasonJan - Mar
- Low SeasonOct - Dec
- Busiest DaySat
- Least Busy DayThu
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Frequently asked questions about your Chicago Union Station, Chicago, IL to Winona Station, Winona, MN trip
Use these quick route answers to check fares, travel time, departure options, and direct services before booking from Chicago Union Station, Chicago, IL to Winona Station, Winona, MN.
Live departures
Chicago Union Station, Chicago, IL to Winona Station, Winona, MN train times
The table below shows live departures for Chicago Union Station, Chicago, IL to Winona Station, Winona, MN trains for today, Monday, November 2. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
1333 Borealis | 11:10 AM Chicago Union Station, Chicago, IL | 5h35 | 4:45 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 | |
27 Empire Builder | 3:05 PM Chicago Union Station, Chicago, IL | 5h29 | 8:34 PM Winona Station, Winona, MN | 0 transfersDirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Train companies
Train companies from Chicago Union Station, Chicago, IL to Winona Station, Winona, MN
Trains from Chicago Union Station, Chicago, IL to Winona Station, Winona, MN 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
Companies, tickets, and onboard amenities between Chicago Union Station, Chicago, IL and Winona Station, Winona, MN
Review the details behind your booking, from operators and ticket rules to luggage, onboard amenities, accessibility, and route-specific travel policies.
FAQs: Trains from Chicago Union Station, Chicago, IL to Winona Station, Winona, MN
Find answers to the most common questions about traveling from Chicago Union Station, Chicago, IL to Winona Station, 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 Station, Winona, MN, this guide helps you travel smarter and with confidence.

popular train stations
Popular train stations from Chicago Union Station, Chicago, IL to Winona Station, Winona, MN
Most Chicago Union Station, Chicago, IL to Winona Station, Winona, MN trains use the Union Station to Winona Station station pair. Use this guide to compare Chicago Union Station, Chicago, IL and Winona Station, Winona, MN train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
Getting to Union Station from Chicago city centre
Union Station is 3 km from Chicago city centre. Public transport options include:
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.
Getting to Winona Station from Winona city centre
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.
