The cheapest and fastest trains from Winona, MN to Chicago, IL
Cheapest price
$40
Average price
$67
Fastest journey
5 h 40 m
Average duration
6 h 37 m
Trains per day
3
Distance
406 km
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 $67 if you buy it on the day, but the cheapest tickets can be found for only $40.
Of the 3 trains that leave Winona, MN for Chicago, IL on Sat, Nov 29, 3 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sat, Nov 29 the direct trains cover the 406 km distance in an average of 6 h 37 m but if you time it right, some trains will get you there in just 5 h 40 m .
On Sat, Nov 29 the slowest trains will take 8 h 20 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.






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 €32. For those with little time consider booking a flight which can get you there in 1h 29m. The ticket price range depends on the travel mode: a train costs an average of €32, and a flight costs an average of €296.
Distance: 252 miles (406 km)
Compare train with
Most popular Train | Bus | Flight |
|---|---|---|
€89 Average price Cheapest | €115 Average price | €335 Average price |
6h 10m Average total duration 5h 40m Onboard + 30m Additional time* | 7h 42m Average total duration 7h 12m Onboard + 30m Additional time* | 4h 29m Average total duration Fastest 1h 29m Onboard + 3h 0m Additional time* |
Direct Options | Direct Options | Direct Options |
Live departures
Winona, MN to Chicago, IL train times
The table below shows live departures for Winona, MN to Chicago, IL trains for today, Friday, November 28. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 4:01 PM Winona, MN | 5h44 | 9:45 PM Chicago, IL | 0 transfersDirect | |
![]() | 6:31 PM Winona, MN | 5h50 | 12:21 AM 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.
Nov 29
Nov 30
Dec 01
Dec 02
Dec 03
Dec 04
Dec 05
Journey information
Overview: Train from Winona, MN to Chicago, IL
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 $40 (€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.
Distance 252 miles (406 km) |
Average train duration 5h 40m |
Cheapest ticket price $40 (€32) |
Trains per day 5 |
Direct trains 3 |
Fastest train 5h 34m |
First train 06:10 |
Last train 15:05 |
Train companies: Amtrak from Winona, MN to Chicago, IL trainsAmtrak trains will get you between Winona, MN and Chicago, IL 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 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.

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