There are 5 ways to get from Winona to Chicago Union Station 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 to La-Crosse-Airport-LSEtaxi
- Fly from La Crosse (LSE) to Chicago O'Hare International Airport (ORD)plane LSE - ORD
2h 57m$98–313Drive to Chippewa Valley Regional Airport, fly
cheapest- Drive from Winona to Eau-Claire-Airport-EAUcar
- Fly from Chippewa Valley Regional Airport (EAU) to Chicago O'Hare International Airport (ORD)plane EAU - ORD
4h 3m$50–264Train (Amtrak)
- Take the train from Winona to Chicago Union Stationtrain Empire Builder / ...
5h 44m$160–260Bus
- 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
7h 56m$71–121Drive 304.1 mi
- Drive from Winona to Chicago Union Stationcar 304.1 mi
4h 58m$56–81
Winona to Chicago Union Station by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Winona to Chicago Union Station is to drive which costs $55 - $80 and takes 4h 58m.
The fastest way to get from Winona to Chicago Union Station is to taxi and fly which takes 2h 57m and costs $95 - $320.
No, there is no direct bus from Winona to Chicago Union Station. 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 7h 56m.
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 and Chicago Union Station is 262 miles. The road distance is 305.9 miles.
The best way to get from Winona to Chicago Union Station without a car is to train which takes 5h 44m and costs $160 - $260.
It takes approximately 2h 57m to get from Winona to Chicago Union Station, including transfers.
Winona to Chicago Union Station bus services, operated by Jefferson Lines, depart from Winona St. University station.
Winona to Chicago Union Station train services, operated by Amtrak, depart from Winona station.
The best way to get from Winona to Chicago Union Station is to train which takes 5h 44m and costs $160 - $260. Alternatively, you can bus, which costs $70 - $130 and takes 7h 56m.
What companies run services between Winona, MN, USA and Chicago Union Station, IL, USA?
Amtrak operates a train from Winona to Chicago Union Station 3 times a day. Tickets cost $160–260 and the journey takes 5h 44m. Alternatively, you can take a bus from Winona St. University to W Jackson Blvd, after S Clinton St via Madison and 250 N. Lake St - Madison UW Campus in around 7h 56m.
- Website
- aa.com
Flights from La Crosse to Chicago O'Hare International Airport
- Ave. Duration
- 1h 30m
- When
- Every day
- Estimated price
- $30–230
- Website
- united.com
Flights from Chippewa Valley Regional Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 29m
- When
- Every day
- Estimated price
- $35–240
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
- $160–260
- 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
- 31 min
- Estimated price
- $65–80
Want to know more about travelling around United States
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Booking & Getting There
Winona to Chicago Union Station bus services, operated by Jefferson Lines, arrive at Madison station.
Winona to Chicago Union Station train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Winona to Chicago Union Station is 306 miles. It takes approximately 4h 58m to drive from Winona to Chicago Union Station.
Book your Winona to Chicago Union Station train tickets online with Omio.
There are 1309+ hotels available in Chicago Union Station.