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  •  5 h 26 min

  1. Take the train from Chicago Union Station to Winona Amtrak Empire Builder

$50 - $140

Cheapest option

Bus  •  8 h

  1. Take the bus from Chicago to Madison - Langdon & N Park
  2. Take the bus from Madison to Winona State University, MN 966

$53 - $83

5 alternative options

Bus via Milwaukee  •  8 h

  1. Take the bus from Chicago, Il to Milwaukee, Wi 4716 / ...
  2. Take the bus from Milwaukee to Winona State University, MN 966

$60 - $104

Drive  •  5 h 12 min

  1. Drive from Chicago to Winona 307.2 miles

$30 - $45

Fly Chicago O'Hare to La Crosse  •  4 h 45 min

  1. Fly from Chicago O'Hare (ORD) to La Crosse (LSE) ORD - LSE

$179 - $682

Fly Chicago O'Hare to Rochester, bus  •  6 h 16 min

  1. Fly from Chicago O'Hare (ORD) to Rochester (RST) ORD - RST
  2. Take the bus from Rochester, MN to Winona, MN

$194 - $751

Fly Chicago Midway to Minneapolis, bus  •  6 h 9 min

  1. Fly from Chicago Midway (MDW) to Minneapolis (MSP) MDW - MSP
  2. Take the bus from Minneapolis-St Paul Airport, MN to Winona State University, MN

$92 - $319

Questions & Answers

The cheapest way to get from Chicago to Winona is to drive which costs $30 - $45 and takes 5 h 12 min.

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The quickest way to get from Chicago to Winona is to fly which costs $170 - $700 and takes 4 h 45 min.

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No, there is no direct bus from Chicago to Winona. However, there are services departing from Chicago and arriving at Winona State University, MN via Madison. The journey, including transfers, takes approximately 8 h.

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Yes, there is a direct train departing from Chicago Union Station station and arriving at Winona Amtrak. Services depart three times a day, and operate every day. The journey takes approximately 5 h 26 min.

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The distance between Chicago and Winona is 254 miles. The road distance is 307.2 miles.

Get driving directions

The best way to get from Chicago to Winona without a car is to train which takes 5 h 26 min and costs $50 - $140.

More details

The train from Chicago Union Station to Winona Amtrak takes 5 h 26 min including transfers and departs three times a day.

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Chicago to Winona bus services, operated by Megabus, depart from Chicago station.

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Chicago to Winona train services, operated by Amtrak, arrive at Chicago Union Station.

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The best way to get from Chicago to Winona is to train which takes 5 h 26 min and costs $50 - $140. Alternatively, you can bus, which costs $50 - $85 and takes 8 h, you could also fly, which costs $170 - $700 and takes 4 h 45 min.

Mode details

Map of how to get from Chicago to Winona.
Launch map view
  • Distance: 253.8 miles
  • Duration: 5 h 26 min

What companies run services between Chicago, IL, USA and Winona, MN, USA?

Amtrak operates a train from Chicago to Winona 3 times a day. Tickets cost $50 - $140 and the journey takes 5 h 26 min. Alternatively, you can take a bus from Chicago to Winona via Madison - Langdon & N Park and Madison in around 8 h.

Airlines
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to Minneapolis
Ave. Duration
1 h 24 min
When
Every day
Estimated price
$85 - $390
Flights from Chicago Midway to Minneapolis via St. Louis
Ave. Duration
3 h 20 min
When
Sunday
Estimated price
$85 - $390
Flights from Chicago Midway to Minneapolis via Kansas City
Ave. Duration
3 h 30 min
When
Sunday
Estimated price
$85 - $390
American Airlines
Website
aa.com
Flights from Chicago O'Hare to La Crosse
Ave. Duration
1 h 6 min
When
Every day
Estimated price
$260 - $850
Flights from Chicago O'Hare to Rochester
Ave. Duration
1 h 9 min
When
Every day
Estimated price
$260 - $750
Delta
Website
delta.com
Flights from Chicago Midway to Minneapolis
Ave. Duration
1 h 35 min
When
Every day
Estimated price
$80 - $390
United Airlines
Website
united.com
Flights from Chicago O'Hare to Rochester
Ave. Duration
1 h 19 min
When
Every day
Estimated price
$150 - $750
Train operators
Amtrak

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 1-800-872-7245
Website
amtrak.com
Train from Chicago Union Station to Winona Amtrak
Ave. Duration
5 h 26 min
Frequency
3 times a day
Estimated price
$50 - $140
Website
amtrak.com
Coach Seat
$50 - $80
Flexi Coach Seat
$95 - $140
Business Coach Seat
$95 - $140
Room
$240 - $340
Bus operators
Jefferson Lines
Phone
800-451-5333
Email
info@jeffersonlines.com
Website
jeffersonlines.com
Bus from Madison to Winona State University, MN
Ave. Duration
3 h 45 min
Frequency
Every 3 hours
Estimated price
$35 - $55
Book at
jeffersonlines.com
Bus from Milwaukee to Winona State University, MN
Ave. Duration
5 h 10 min
Frequency
Every 3 hours
Estimated price
$45 - $70
Book at
jeffersonlines.com
Bus from Minneapolis-St Paul Airport, MN to Winona State University, MN
Ave. Duration
2 h 20 min
Frequency
Every 3 hours
Estimated price
$30 - $45
Book at
jeffersonlines.com
Greyhound USA

Greyhound is a leading bus company based in Dallas, Texas, serving over 3800 destinations across North America, Mexico and Canada. Greyhound carries around 18 million passengers a year who travel 5.4 billion miles (8.6 billion km) a year on their fleet of around 1700 vehicles. For travel flexibility, you can board or get off a Greyhound bus at official Greyhound stations, partner stations and curbside stops. There are around 230 Greyhound stations across the US where you can both catch your bus and buy tickets, that are also available on the official website and via the mobile app.

Rome2rio's guide to Greyhound USA
Contact Details
Phone
+1 214-849-8100/1-800-231-2222
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from Chicago, Il to Milwaukee, Wi
Ave. Duration
1 h 50 min
Frequency
Every 30 minutes
Estimated price
$15 - $35
Website
greyhound.com
Economy
$15 - $23
Flexible
$27 - $35
Go Carefree Shuttle
Website
gocarefreeshuttle.com
Bus from Rochester, MN to Winona, MN
Ave. Duration
1 h 20 min
Frequency
Every 4 hours
Estimated price
$35
Schedules at
gocarefreeshuttle.com

Want to know more about travelling around United States

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