The cheapest and fastest trains from Chicago, IL to Winona, MN
Cheapest price
$49
Average price
$70
Fastest journey
5 h 29 m
Average duration
5 h 29 m
Trains per day
2
Distance
406 km
The best way to find a cheap train ticket from Chicago, IL to 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, IL to Winona, MN will cost around $70 if you buy it on the day, but the cheapest tickets can be found for only $49.
Of the 2 trains that leave Chicago, IL for Winona, MN on Fri, Jun 05, 2 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Fri, Jun 05 the direct trains cover the 406 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 Fri, Jun 05 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.
8:05 PM5h29Chicago, IL1:34 AMWinona, MN$491One-way0 transfers
9:05 PM5h29Chicago, IL2:34 AMWinona, MN$901One-way0 transfers
9:05 PM5h29Chicago, IL2:34 AMWinona, MN$901One-way0 transfers
8:05 PM5h29Chicago, IL1:34 AMWinona, MN$491One-way0 transfers
Travel Information
Compare train, bus, and flight for Chicago, IL to Winona, MN
Omio recommends booking the train as it is the most popular option from Chicago, IL to Winona, MN among Omio's users. If you are prioritising price take the bus with prices starting from $115. 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 bus costs an average of $115, and a flight costs an average of $373.
Distance: 252 miles (406 km)
Compare train with
Most popular Train | Flight | Bus | Driving |
|---|---|---|---|
$162 Average price | $430 Average price | $118 Average price Cheapest | $67 Average price (fuel + tolls) |
6h 1m Average total duration 5h 31m 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* | 5h 34m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Chicago, IL to Winona, MN:
A bus is $44 (€36) less than a train for this route with tickets for a train from Chicago, IL to Winona, MN costing on average $162 (€131).
A bus is $312 (€252) less than a flight for this route with tickets for a flight from Chicago, IL to Winona, MN costing on average $430 (€347).
Other travel options to Winona, MN take longer:
Train takes on average 5h 31m.
Bus takes on average 7h 23m.
You'll arrive about 3m sooner (5h 31m by train vs 5h 34m by car). Tickets start at around $162 (€131) compared to roughly $67 (€54) in fuel and tolls — so you're paying a bit more, but getting hours of your day back, a city-centre arrival, and the freedom to work or relax instead of drive.
Direct services run with Amtrak.
Driving makes more sense if you're travelling as a group (where fuel costs split several ways), want to stop along the way, or need a car once you arrive.
Live departures
Chicago, IL to Winona, MN train times
The table below shows live departures for Chicago, IL to Winona, MN trains for today, Thursday, June 4. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 8:05 PM Chicago, IL | 5h29 | 1:34 AM Winona, MN | 0 transfersDirect | |
![]() | 9:05 PM Chicago, IL | 5h29 | 2:34 AM 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, IL to 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 05
Jun 06
Jun 07
Jun 08
Jun 09
Jun 10
Jun 11
Journey information
Overview: Train from Chicago, IL to Winona, MN
Trains from Chicago, IL to Winona, MN run on average 4 times per day, taking around 5h 31m. 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 29m.
Distance 252 miles (406 km) |
Average train duration 5h 31m |
Cheapest ticket price $39 (€32) |
Trains per day 4 |
Direct trains 3 |
Fastest train 5h 29m |
First train 6:10 AM |
Last train 3:05 PM |
Cheapest Month Sep |
Cheapest Day Fri |
High Season Jan - Mar |
Low Season Jul - Sep |
Best time to book 49 days |
Train companies: Amtrak from Chicago, IL to Winona, MN trainsAmtrak trains will get you between Chicago, IL and 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, IL to Winona, MN
Find answers to the most common questions about traveling from Chicago, IL to 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, MN, this guide helps you travel smarter and with confidence.

popular train stations
Popular train stations from Chicago, IL to 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
Most popular train connections from Chicago, IL
More options for your journey from Chicago, IL to Winona, MN
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