There are 7 ways to get from Chicago to Winona by train, bus, car or plane
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Recommended option
Train • 5h 29m
6 alternative options
Bus • 8h
Drive • 5h
Fly Chicago O'Hare to Rochester, bus • 6h 12m
Chicago to Winona by train
Questions & Answers
The cheapest way to get from Chicago to Winona is to train which costs $12 - $130 and takes 5h 29m.
The fastest way to get from Chicago to Winona is to fly and train which takes 4h 42m and costs $270 - $650.
No, there is no direct bus from Chicago station to Winona. However, there are services departing from Chicago Union Station and arriving at Winona State University, MN via Madison, WI-Lake St.. The journey, including transfers, takes approximately 8h.
Yes, there is a direct train departing from Chicago Union Station station and arriving at Winona. Services depart five times a day, and operate every day. The journey takes approximately 5h 29m.
The distance between Chicago and Winona is 308 miles. The road distance is 306.7 miles.
The best way to get from Chicago to Winona without a car is to train which takes 5h 29m and costs $12 - $130.
The train from Chicago Union Station to Winona takes 5h 29m including transfers and departs five times a day.
Chicago to Winona bus services, operated by Amtrak, depart from Chicago Union Station.
Chicago to Winona train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Chicago to Winona is to train which takes 5h 29m and costs $12 - $130. Alternatively, you can bus, which costs $55 - $130 and takes 8h.
- Distance: 308.2 miles
- Duration: 5h 29m
What companies run services between Chicago, IL, USA and Winona, MN, USA?
Amtrak operates a train from Chicago Union Station to Winona 5 times a day. Tickets cost $12 - $130 and the journey takes 5h 29m. Alternatively, you can take a bus from Chicago to Winona via Madison and Madison, WI-Lake St. in around 8h.
- Website
- aa.com
Flights from Chicago O'Hare to La Crosse
- Ave. Duration
- 1h 16m
- When
- Every day
- Estimated price
- $260 - $650
Flights from Chicago O'Hare to Rochester
- Ave. Duration
- 1h 18m
- When
- Every day
- Estimated price
- $260 - $550
Flights from Chicago O'Hare to Minneapolis
- Ave. Duration
- 1h 31m
- When
- Every day
- Estimated price
- $95 - $380
- Website
- southwest.com
Flights from Chicago Midway to Minneapolis
- Ave. Duration
- 1h 25m
- When
- Every day
- Estimated price
- $95 - $270
Flights from Chicago Midway to Minneapolis via Kansas City
- Ave. Duration
- 3h 40m
- When
- Monday, Thursday and Friday
- Estimated price
- $95 - $270
- Website
- united.com
Flights from Chicago O'Hare to Minneapolis
- Ave. Duration
- 1h 31m
- When
- Every day
- Estimated price
- $110 - $380
- Website
- delta.com
Flights from Chicago Midway to Minneapolis
- Ave. Duration
- 1h 39m
- When
- Every day
- Estimated price
- $140 - $550
Flights from Chicago O'Hare to Minneapolis
- Ave. Duration
- 1h 32m
- When
- Every day
- Estimated price
- $120 - $440
- Website
- suncountry.com
Flights from Chicago O'Hare to Minneapolis
- Ave. Duration
- 1h 34m
- When
- Monday, Thursday, Friday and Sunday
- Estimated price
- $60 - $420
Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Winona
- Ave. Duration
- 5h 29m
- Frequency
- 5 times a day
- Estimated price
- $12 - $130
- Website
- https://www.amtrak.com/home.html
- Child Coach - Advance Purchase
- $12 - $50
- Child Coach - short notice
- $29 - $45
- Child Business Class - advance purchase
- $25 - $80
- Child Business Class - short notice
- $27 - $80
- Coach Seat - Advance Purchase
- $35 - $80
- Business Seat - advance purchase
- $50 - $160
- Business Seat - short notice
- $55 - $150
- Coach Seat - short notice
- $35 - $130
Train from La Crosse to Winona
- Ave. Duration
- 30 min
- Frequency
- 5 times a day
- Estimated price
- $1 - $60
- Website
- https://www.amtrak.com/home.html
- Child Coach - Advance Purchase
- $1 - $16
- Child Coach - short notice
- $7 - $19
- Child Business Class - advance purchase
- $10 - $35
- Child Business Class - short notice
- $11 - $40
- Coach Seat - Advance Purchase
- $9 - $24
- Business Seat - advance purchase
- $22 - $70
- Business Seat - short notice
- $28 - $50
- Coach Seat - short notice
- $5 - $60
Train from St. Paul-Minneapolis to Winona
- Ave. Duration
- 2h 4m
- Frequency
- 5 times a day
- Estimated price
- $4 - $80
- Website
- https://www.amtrak.com/home.html
- Child Coach - Advance Purchase
- $4 - $24
- Child Coach - short notice
- $15 - $26
- Child Business Class - advance purchase
- $14 - $45
- Child Business Class - short notice
- $16 - $50
- Coach Seat - Advance Purchase
- $20 - $35
- Business Seat - advance purchase
- $30 - $95
- Business Seat - short notice
- $35 - $80
- Coach Seat - short notice
- $13 - $80
Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Bus from Chicago Union Station to Madison
- Ave. Duration
- 3h 35m
- Frequency
- Hourly
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 608-752-5407
- vangalder@coachusa.com
Bus from Chicago Union Station to Madison, WI-Lake St.
- Ave. Duration
- 3h 40m
- Frequency
- Every 2 hours
- Estimated price
- $23 - $40
- Website
- https://www.coachusa.com/van-galder-bus-company
- Phone
- +1-858-800-8898
- info@jeffersonlines.com
- Website
- jeffersonlines.com
Bus from Madison, WI-Lake St. to Winona State University, MN
- Ave. Duration
- 3h 25m
- Frequency
- Once daily
- Estimated price
- $35 - $85
- Book at
- https://www.jeffersonlines.com/
Bus from Rochester, MN to Winona State University, MN
- Ave. Duration
- 55 min
- Frequency
- Twice daily
- Estimated price
- $21 - $50
- Book at
- https://www.jeffersonlines.com/
Want to know more about travelling around United States
Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.
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Read the travel guideMore Questions & Answers
Chicago to Winona bus services, operated by Jefferson Lines, arrive at Winona State University, MN station.
Chicago to Winona train services, operated by Amtrak, arrive at Winona station.
Yes, the driving distance between Chicago to Winona is 307 miles. It takes approximately 5h to drive from Chicago to Winona.
Book your Chicago to Winona train tickets online with Omio.
There are seven+ hotels available in Winona. Prices start at $41 USD per night.