The cheapest and fastest trains from Chicago Union Station, Chicago, IL to Winona Station, Winona, MN
Cheapest price
$169
Average price
$169
Fastest journey
5 h 29 m
Average duration
5 h 29 m
Trains per day
2
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 $169 if you buy it on the day, but the cheapest tickets can be found for only $169.
Of the 2 trains that leave Chicago Union Station, Chicago, IL for Winona Station, Winona, MN on Sat, Jun 20, 2 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sat, Jun 20 the direct trains cover the 405 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 Sat, Jun 20 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.
7 Empire Builder3:05 PM5h29Chicago Union Station, Chicago, IL8:34 PMWinona Station, Winona, MN$1691One-way0 transfers
27 Empire Builder3:05 PM5h29Chicago Union Station, Chicago, IL8:34 PMWinona Station, Winona, MN$1691One-way0 transfers
7 Empire Builder3:05 PM5h29Chicago Union Station, Chicago, IL8:34 PMWinona Station, Winona, MN$1691One-way0 transfers
27 Empire Builder3:05 PM5h29Chicago Union Station, Chicago, IL8:34 PMWinona Station, Winona, MN$1691One-way0 transfers
Travel Information
Compare train, bus, 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 $39. 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 train costs an average of $39, and a flight costs an average of $365.
Distance: 251 miles (405 km)
Compare train with
Most popular Train | Flight | Bus | Driving |
|---|---|---|---|
$101 Average price Cheapest | $417 Average price | $131 Average price | $66 Average price (fuel + tolls) |
6h 4m Average total duration 5h 34m 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* | 4h 27m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Chicago Union Station, Chicago, IL to Winona Station, Winona, MN:
A train is $30 (€24) less than a bus for this route with tickets for a bus from Chicago Union Station, Chicago, IL to Winona Station, Winona, MN costing on average $131 (€107).
A train is $316 (€259) less than a flight for this route with tickets for a flight from Chicago Union Station, Chicago, IL to Winona Station, Winona, MN costing on average $417 (€342).
Other travel options to Winona Station, Winona, MN take longer:
Train takes on average 5h 34m.
Bus takes on average 7h 23m.
Tickets start at around $101 (€83) compared to roughly $66 (€54) in fuel and tolls — a saving of about $-34.78 (€-28.50). The journey takes 5h 34m versus 4h 27m 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
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, Friday, June 19. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
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 | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Chicago Union Station, Chicago, IL to Winona Station, 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.
Jun 20
Jun 21
Jun 22
Jun 23
Jun 24
Jun 25
Jun 26
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 34m. 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 11:10, 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 34m |
Cheapest ticket price $39 (€32) |
Trains per day 4 |
Direct trains 3 |
Fastest train 5h 29m |
First train 11:10 AM |
Last train 9:05 PM |
Cheapest Month Dec |
Cheapest Day Wed |
High Season Jan - Mar |
Low Season Oct - Dec |
Busiest Day Sat |
Least Busy Day Fri |
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 $39 (€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
