How to get from Chicago to Winona

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 Amtrak to Winona Amtrak Empire Builder

$50 - $140

6 alternative options

Bus  •  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

Amtrak Thruway, bus  •  9 h 15 min

  1. Take the Amtrak Thruway from Chicago, IL to Madison, WI - Univ. of Wisconsin 8960
  2. Take the bus from Madison to Winona State University, MN 966

$65 - $85

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 48 min

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

$179 - $682

Fly Chicago Midway to Minneapolis, bus  •  6 h 8 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

Fly Chicago O'Hare to Rochester, bus  •  6 h 27 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

Questions & Answers

The distance between Chicago and Winona is 406 km. The road distance is 491 km.

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

The quickest way to get from Chicago to Winona is to fly which takes 4 h 48 min and costs $170 - $700.

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

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.

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

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.

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 25 min
When
Sunday
Estimated price
$85 - $390
American Airlines
Website
aa.com
Flights from Chicago O'Hare to La Crosse
Ave. Duration
1 h 9 min
When
Every day
Estimated price
$260 - $850
Flights from Chicago O'Hare to Rochester
Ave. Duration
1 h 17 min
When
Every day
Estimated price
$260 - $750
Delta
Website
delta.com
Flights from Chicago Midway to Minneapolis
Ave. Duration
1 h 32 min
When
Every day
Estimated price
$80 - $390
Flights from Chicago O'Hare to Rochester via Minneapolis
Ave. Duration
3 h 4 min
When
Saturday
Estimated price
$320 - $750
United Airlines
Website
united.com
Flights from Chicago O'Hare to Rochester
Ave. Duration
1 h 20 min
When
Every day
Estimated price
$150 - $750
Train operators
Amtrak
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Chicago Union Station Amtrak 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
Greyhound USA
Phone
+1 214-849-8100
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
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
Every 3 hours
Estimated price
$45 - $70
Schedules at
jeffersonlines.com
Bus from Madison to Winona State University, MN
Ave. Duration
3 h 45 min
Frequency
Every 3 hours
Estimated price
$35 - $55
Schedules 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
Schedules at
jeffersonlines.com
Vangalder Bus
Phone
+1 608-752-5407
Email
vangalder@coachusa.com
Bus from Chicago, IL - Amtrak to Madison, WI
Ave. Duration
3 h 35 min
Frequency
Once daily
Estimated price
$30
Schedules at
vangalderbus.com
Book at
govangalder.com
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

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