There are 5 ways to get from Winona (Station) to Chicago by taxi, plane, train (Amtrak), bus, or car
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Taxi to La Crosse, fly
best- Take the taxi from Winona (Station) to La-Crosse-Airport-LSEtaxi
- Fly from La Crosse (LSE) to Chicago O'Hare International Airport (ORD)plane LSE - ORD
2h 40m$102–332Drive to Chippewa Valley Regional Airport, fly
cheapest- Drive from Winona (Station) to Eau-Claire-Airport-EAUcar
- Fly from Chippewa Valley Regional Airport (EAU) to Chicago O'Hare International Airport (ORD)plane EAU - ORD
3h 50m$50–284Train (Amtrak)
- Take the train from Winona to Chicago Union Stationtrain Empire Builder / ...
5h 44m$80–190Bus
- Take the bus from Winona St. University to Madisonbus Jefferson Lines 965
- Take the bus from 250 N. Lake St - Madison UW Campus to W Jackson Blvd, after S Clinton Stbus Van Galder
8h 6m$71–121Drive 304.4 mi
- Drive from Winona (Station) to Chicagocar 304.4 mi
4h 59m$56–81
Winona (Station) to Chicago by train (Amtrak)
Questions & Answers
The cheapest way to get from Winona (Station) to Chicago is to drive which costs $55 - $80 and takes 4h 59m.
The fastest way to get from Winona (Station) to Chicago is to taxi and fly which takes 2h 40m and costs $100 - $340.
No, there is no direct bus from Winona (Station) to Chicago. However, there are services departing from Winona St. University and arriving at W Jackson Blvd, after S Clinton St via 250 N. Lake St - Madison UW Campus. The journey, including transfers, takes approximately 8h 6m.
Yes, there is a direct train departing from Winona and arriving at Chicago Union Station station. Services depart three times a day, and operate every day. The journey takes approximately 5h 44m.
The distance between Winona (Station) and Chicago is 261 miles. The road distance is 306.1 miles.
The best way to get from Winona (Station) to Chicago without a car is to train which takes 5h 44m and costs $80 - $190.
It takes approximately 2h 40m to get from Winona (Station) to Chicago, including transfers.
Winona (Station) to Chicago bus services, operated by Jefferson Lines, depart from Winona St. University station.
Winona (Station) to Chicago train services, operated by Amtrak, depart from Winona station.
The best way to get from Winona (Station) to Chicago is to train which takes 5h 44m and costs $80 - $190. Alternatively, you can bus, which costs $70 - $130 and takes 8h 6m.
What companies run services between Winona (Station), MN, USA and Chicago, IL, USA?
Amtrak operates a train from Winona to Chicago Union Station 3 times a day. Tickets cost $80–190 and the journey takes 5h 44m. Alternatively, you can take a vehicle from Winona (Station) to W Jackson Blvd, after S Clinton St via Winona St. University, Madison, and 250 N. Lake St - Madison UW Campus in around 8h 6m.
- Website
- aa.com
Flights from La Crosse to Chicago O'Hare International Airport
- Ave. Duration
- 1h 34m
- When
- Every day
- Estimated price
- $35–250
- Website
- united.com
Flights from La Crosse to Chicago O'Hare International Airport
- Ave. Duration
- 1h 24m
- When
- Every day
- Estimated price
- $35–250
Flights from Chippewa Valley Regional Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 30m
- When
- Every day
- Estimated price
- $35–260
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Winona to Chicago Union Station
- Ave. Duration
- 5h 44m
- Frequency
- 3 times a day
- Estimated price
- $80–190
- Website
- Amtrak
- Phone
- +1-858-800-8898
- Website
- jeffersonlines.com
Bus from Winona St. University to Madison
- Ave. Duration
- 3h 20m
- Frequency
- Once daily
- Estimated price
- $40–65
- Book at
- Jefferson Lines
- Adult
- $40–65
- Phone
- +1 (866) 912 - 6224
- [email protected]
- Website
- Rockland Coaches
Bus from 250 N. Lake St - Madison UW Campus to W Jackson Blvd, after S Clinton St
- Ave. Duration
- 4h
- Frequency
- Hourly
- Estimated price
- $26–60
- Schedules at
- Rockland Coaches
- Adult
- $26–60
- Ave. Duration
- 30 min
- Estimated price
- $65–80
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More Questions & Answers
Winona (Station) to Chicago bus services, operated by Jefferson Lines, arrive at Madison station.
Winona (Station) to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Winona (Station) to Chicago is 306 miles. It takes approximately 4h 59m to drive from Winona (Station) to Chicago.
Book your Winona (Station) to Chicago train tickets online with Omio.
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