The cheapest and fastest trains from Chicago Union Station, Chicago, IL to Winona Station, Winona, MN
Cheapest price
$50
Average price
$75
Fastest journey
5 h 29 m
Average duration
7 h 15 m
Trains per day
5
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 $75 if you buy it on the day, but the cheapest tickets can be found for only $50.
Of the 5 trains that leave Chicago Union Station, Chicago, IL for Winona Station, Winona, MN on Wed, May 06, 3 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Wed, May 06 the direct trains cover the 405 km distance in an average of 7 h 15 m but if you time it right, some trains will get you there in just 5 h 29 m .
On Wed, May 06 the slowest trains will take 10 h 50 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.
1333 Borealis11:10 AM5h50Chicago Union Station, Chicago, IL5:00 PMWinona Station, Winona, MN$501One-way0 transfers
329 Hiawatha Service · 1333 Borealis6:10 AM10h50Chicago Union Station, Chicago, IL5:00 PMWinona Station, Winona, MN$661One-way1 transfer
331 Hiawatha Service · 1333 Borealis8:25 AM8h35Chicago Union Station, Chicago, IL5:00 PMWinona Station, Winona, MN$711One-way1 transfer
27 Empire Builder3:05 PM5h29Chicago Union Station, Chicago, IL8:34 PMWinona Station, Winona, MN$941One-way0 transfers
7 Empire Builder3:05 PM5h29Chicago Union Station, Chicago, IL8:34 PMWinona Station, Winona, MN$941One-way0 transfers
27 Empire Builder3:05 PM5h29Chicago Union Station, Chicago, IL8:34 PMWinona Station, Winona, MN$941One-way0 transfers
7 Empire Builder3:05 PM5h29Chicago Union Station, Chicago, IL8:34 PMWinona Station, Winona, MN$941One-way0 transfers
1333 Borealis11:10 AM5h50Chicago Union Station, Chicago, IL5:00 PMWinona Station, Winona, MN$501One-way0 transfers
331 Hiawatha Service · 1333 Borealis8:25 AM8h35Chicago Union Station, Chicago, IL5:00 PMWinona Station, Winona, MN$711One-way1 transfer
329 Hiawatha Service · 1333 Borealis6:10 AM10h50Chicago Union Station, Chicago, IL5:00 PMWinona Station, Winona, MN$661One-way1 transfer
Travel Information
Compare bus, train, and flight for Chicago Union Station, Chicago, IL to Winona Station, Winona, MN
Omio recommends booking the train as it is the most popular option from Chicago Union Station, Chicago, IL to Winona Station, Winona, MN among Omio's users. If you are prioritising price take the train with prices starting from $40. For those with little time consider booking a flight which can get you there in 1h 24m. The ticket price range depends on the travel mode: a train costs an average of $40, and a flight costs an average of $366.
Distance: 251 miles (405 km)
Compare train with
Most popular Train | Flight | Bus |
|---|---|---|
$87 Average price Cheapest | $409 Average price | $134 Average price |
6h 0m Average total duration 5h 30m Onboard + 30m Additional time* | 4h 24m Average total duration Fastest 1h 24m Onboard + 3h 0m Additional time* | 7h 53m Average total duration 7h 23m Onboard + 30m Additional time* |
Direct Options | Direct Options | Direct Options |
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, Tuesday, May 5. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
329 Hiawatha Service · 1333 Borealis | 6:10 AM Chicago Union Station, Chicago, IL | 10h50 | 5:00 PM Winona Station, Winona, MN | 1 transfer | |
331 Hiawatha Service · 1333 Borealis | 8:25 AM Chicago Union Station, Chicago, IL | 8h35 | 5:00 PM Winona Station, Winona, MN | 1 transfer | |
1333 Borealis | 11:10 AM Chicago Union Station, Chicago, IL | 5h50 | 5:00 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
Compare prices and tickets Chicago Union Station, Chicago, IL to Winona Station, Winona, MN by bus, train, or flight
Compare bus, train, 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.
May 06
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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 30m. Cheap train tickets for this journey start at $40 (€32) if you book in advance.
There are 3 trains per day. The earliest train runs at 17:10, the last at 21:05. The fastest train covers the 251 miles (405 km) distance in 5h 29m.
Distance 251 miles (405 km) |
Average train duration 5h 30m |
Cheapest ticket price $40 (€32) |
Trains per day 4 |
Direct trains 3 |
Fastest train 5h 29m |
First train 5:10 PM |
Last train 9:05 PM |
Cheapest Month Feb |
Cheapest Day Wed |
High Season Jan - Mar |
Low Season Apr - Jun |
Busiest Day Thu |
Least Busy Day Thu |
Train companies: Amtrak from Chicago Union Station, Chicago, IL to Winona Station, Winona, MN trainsAmtrak trains will get you between Chicago Union Station, Chicago, IL and Winona Station, Winona, MN from $40 (€32). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
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
- 5:00 AM - 12:00 AM Monday - Sunday
- Free
- 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.
- The Chicago Firehouse Restaurant
- Lou Mitchell's
- Outside the main entrance.
- Elevators, ramps, restrooms.
- $1
- The Kimpton Gray Hotel
- JW Marriott Chicago
- W Chicago - City Center
- Located in the main hall
- Located in the main hall
- Avis
- Budget
- Enterprise
- Located in the main hall
- Free
- Hall 1: main entrance, Amtrak services
- Hall 2: Metra services
- Hall 3: food court and retail shops
- Bus: Several lines available
- CTA: Blue Line, Pink Line
- Parking is available near the station.
- Outside the station.
- Ramps, restrooms.
- Holiday Inn Express & Suites Winona
- AmericInn by Wyndham Winona
- Fairfield Inn & Suites by Marriott Winona
- The station consists of a single platform with shelter.
- Bus: Local bus services available
- Taxi: Local taxi services available
