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There are 6 ways to get from Chicago to Winona by train, bus, car, plane or shuttle

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 Station Empire Builder

$50 - $140

5 alternative options

Bus  •  8 h 30 min

  1. Take the bus from Chicago, Il to Milwaukee, Wi 4712 / ...
  2. Take the bus from Milwaukee to Winona State University, MN 966

$61 - $105

Drive  •  5 h 12 min

  1. Drive from Chicago to Winona 307.2 miles

$30 - $45

Fly Chicago O'Hare to Rochester, shuttle  •  4 h 57 min

  1. Fly from Chicago O'Hare (ORD) to Rochester (RST) ORD - RST
  2. Take a shuttle bus from Rochester Airport to Winona Amtrak Station

$178 - $745

Fly Chicago O'Hare to La Crosse  •  4 h 49 min

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

$179 - $682

Fly Chicago Midway to Minneapolis, bus  •  6 h 14 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 49 min.

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No, there is no direct bus from Chicago to Winona. However, there are services departing from Chicago, Il and arriving at Winona State University, MN via Milwaukee. The journey, including transfers, takes approximately 8 h 30 min.

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Yes, there is a direct train departing from Chicago Union Station station and arriving at Winona Amtrak Station station. 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.

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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.

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

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Chicago to Winona bus services, operated by Greyhound USA, depart from Chicago, Il 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 $60 - $110 and takes 8 h 30 min, you could also fly, which costs $170 - $700 and takes 4 h 49 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 Milwaukee, Wi and Milwaukee in around 8 h 30 min.

Airlines
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to Minneapolis
Ave. Duration
1 h 26 min
When
Every day
Estimated price
$85 - $390
Flights from Chicago Midway to Minneapolis via St. Louis
Ave. Duration
3 h 26 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$85 - $390
Flights from Chicago Midway to Minneapolis via Kansas City
Ave. Duration
3 h 40 min
When
Sunday
Estimated price
$85 - $390
American Airlines
Website
aa.com
Flights from Chicago O'Hare to Rochester
Ave. Duration
1 h 13 min
When
Every day
Estimated price
$260 - $750
Flights from Chicago O'Hare to La Crosse
Ave. Duration
1 h 13 min
When
Every day
Estimated price
$260 - $850
Delta
Website
delta.com
Flights from Chicago Midway to Minneapolis
Ave. Duration
1 h 40 min
When
Every day
Estimated price
$80 - $390
United Airlines
Website
united.com
Flights from Chicago O'Hare to Rochester
Ave. Duration
1 h 21 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
+1 215-856-7924
Website
amtrak.com
Train from Chicago Union Station to Winona Amtrak Station
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
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
2 h 20 min
Frequency
Every 4 hours
Estimated price
$15 - $35
Website
greyhound.com
Economy
$15 - $23
Flexible
$28 - $35
Jefferson Lines
Phone
800-451-5333
Email
info@jeffersonlines.com
Website
jeffersonlines.com
Bus from Milwaukee to Winona State University, MN
Ave. Duration
5 h 10 min
Frequency
Once daily
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
Once daily
Estimated price
$30 - $45
Book at
jeffersonlines.com
Groome Transport
Website
groometransportation.com
Shuttle from Rochester Airport to Winona Amtrak Station
Ave. Duration
1 h 5 min
Frequency
Every 4 hours
Estimated price
$26 - $40
Schedules at
groometransportation.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.

More Questions & Answers

The quickest flight from Chicago O'Hare Airport to Rochester Airport is the direct flight which takes 1 h 10 min.

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Chicago to Winona bus services, operated by Jefferson Lines, arrive at Winona State University, MN station.

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

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Yes, the driving distance between Chicago to Winona is 307 miles. It takes approximately 5 h 12 min to drive from Chicago to Winona.

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United Airlines and American Airlines offer flights from Chicago O'Hare Airport to Rochester Airport.

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Book your Chicago to Winona train tickets online with Rome2rio.

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There are seven+ hotels available in Winona. Prices start at $100 USD per night.

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The best way to get from Chicago to Chicago O'Hare Airport is to subway which takes 42 min and costs $2 - $5.

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