There are 8 ways to get from Jackson to Winona by plane, taxi, train (Amtrak), bus (Greyhound, Flixbus), car, train, or bus
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly to La Crosse, taxi
best- Fly from Jackson/Vicksburg (JAN) to La Crosse (LSE)plane JAN - LSE
- Take the taxi from La-Crosse-Airport-LSE to Winonataxi
9h 26m$214–676Fly to The Eastern Iowa Airport, drive
cheapest- Fly from Jackson/Vicksburg (JAN) to The Eastern Iowa Airport (CID)plane JAN - CID
- Drive from Cedar-Rapids-Airport-CID to Winonacar
8h 49m$159–556Train (Amtrak)
- Take the train from Jackson to Chicago Union Stationtrain City of New Orleans
- Take the train from Chicago Union Station to Winonatrain Empire Builder / ...
22h 4m$269–672Bus
- Take the bus from Jackson to Memphis Bus Stationbus
- Take the bus from Memphis Bus Station to Chicago Bus Stationbus
- Take the bus from Chicago Bus Station to Milwaukee Intermodal Stationbus
- Take the bus from Milwaukee to Winona St. Universitybus
22h 30m$187–301Drive 925.1 mi
- Drive from Jackson to Winonacar 925.1 mi
16h 26m$169–244Fly to Minneapolis–Saint Paul International Airport, train
- Fly from Jackson/Vicksburg (JAN) to Minneapolis–Saint Paul International Airport (MSP)plane JAN - MSP
- Take the train from St. Paul-Minneapolis to Winonatrain
9h 8m$177–714Fly to Dane County Regional Airport-Truax Field, bus
- Fly from Jackson/Vicksburg (JAN) to Dane County Regional Airport-Truax Field (MSN)plane JAN - MSN
- Take the bus from Madison to Winona St. Universitybus
10h 28m$221–813Train, bus
- Take the train from Jackson to Chicago Union Stationtrain
- Take the bus from W Jackson Blvd, after S Clinton St to 250 N. Lake St - Madison UW Campusbus
- Take the bus from Madison to Winona St. Universitybus
24h 17m$259–592
Jackson to Winona by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Jackson to Winona is to drive which costs $160 - $250 and takes 16h 26m.
The fastest way to get from Jackson to Winona is to fly and drive which takes 8h 49m and costs $150 - $600.
No, there is no direct bus from Jackson to Winona. However, there are services departing from Jackson and arriving at Winona St. University via Memphis Bus Station, Chicago Bus Station and Milwaukee. The journey, including transfers, takes approximately 22h 30m.
No, there is no direct train from Jackson to Winona. However, there are services departing from Jackson and arriving at Winona via Chicago Union Station. The journey, including transfers, takes approximately 22h 4m.
The distance between Jackson and Winona is 844 miles. The road distance is 930.5 miles.
The best way to get from Jackson to Winona without a car is to train which takes 22h 4m and costs $260 - $700.
It takes approximately 9h 26m to get from Jackson to Winona, including transfers.
Jackson to Winona bus services, operated by Greyhound USA, depart from Jackson station.
Jackson to Winona train services, operated by Amtrak, depart from Jackson station.
The best way to get from Jackson to Winona is to train which takes 22h 4m and costs $260 - $700. Alternatively, you can bus, which costs $180 - $310 and takes 22h 30m.
What companies run services between Jackson, MS, USA and Winona, MN, USA?
You can take a train from Jackson to Winona via Chicago Union Station in around 22h 4m. Alternatively, you can take a bus from Jackson to Winona St. University via Memphis Bus Station, Chicago Bus Station, Milwaukee Intermodal Station, and Milwaukee in around 22h 30m.
- Website
- aa.com
Flights from Jackson/Vicksburg to La Crosse via Dallas/Ft.Worth, Chicago O'Hare
- Ave. Duration
- 12h 17m
- When
- Every day
- Estimated price
- $110–550
Flights from Jackson/Vicksburg to La Crosse via Charlotte, Chicago O'Hare
- Ave. Duration
- 12h 29m
- When
- Every day
- Estimated price
- $110–550
Flights from Jackson/Vicksburg to La Crosse via Miami, Chicago O'Hare
- Ave. Duration
- 11h 55m
- When
- Saturday
- Estimated price
- $160–700
Flights from Jackson/Vicksburg to La Crosse via Reagan Washington, Chicago O'Hare
- Ave. Duration
- 12h 6m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $130–600
Flights from Jackson/Vicksburg to Minneapolis–Saint Paul International Airport via Dallas/Ft.Worth
- Ave. Duration
- 5h 44m
- When
- Every day
- Estimated price
- $130–650
Flights from Jackson/Vicksburg to Minneapolis–Saint Paul International Airport via Charlotte
- Ave. Duration
- 6h 47m
- When
- Monday, Wednesday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $140–700
Flights from Jackson/Vicksburg to The Eastern Iowa Airport via Dallas/Ft.Worth
- Ave. Duration
- 6h 30m
- When
- Every day
- Estimated price
- $95–470
Flights from Jackson/Vicksburg to The Eastern Iowa Airport via Reagan Washington
- Ave. Duration
- 6h 2m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $130–600
Flights from Jackson/Vicksburg to The Eastern Iowa Airport via Charlotte
- Ave. Duration
- 9h 7m
- When
- Every day
- Estimated price
- $100–550
Flights from Jackson/Vicksburg to Dane County Regional Airport-Truax Field via Dallas/Ft.Worth
- Ave. Duration
- 5h 18m
- When
- Every day
- Estimated price
- $160–800
Flights from Jackson/Vicksburg to Dane County Regional Airport-Truax Field via Charlotte
- Ave. Duration
- 6h 17m
- When
- Monday, Thursday, Friday, Saturday, Sunday, and Wednesday
- Estimated price
- $160–800
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Jackson to Chicago Union Station
- Ave. Duration
- 15h 35m
- Frequency
- Once daily
- Estimated price
- $190–480
- Website
- Amtrak
Train from Chicago Union Station to Winona
- Ave. Duration
- 5h 29m
- Frequency
- 3 times a day
- Estimated price
- $75–200
- Website
- Amtrak
Train from St. Paul-Minneapolis to Winona
- Ave. Duration
- 2h 4m
- Frequency
- 3 times a day
- Estimated price
- $26–65
- Website
- Amtrak
Train from Jackson to Chicago Union Station
- Ave. Duration
- 15h 35m
- Frequency
- Once daily
- Estimated price
- $190–480
- Website
- Amtrak
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Jackson to Memphis Bus Station
- Ave. Duration
- 3h 25m
- Frequency
- Once daily
- Estimated price
- $30–55
- Website
- Greyhound
Bus from Memphis Bus Station to Chicago Bus Station
- Ave. Duration
- 9h 40m
- Frequency
- Once daily
- Estimated price
- $85–140
- Website
- Greyhound
Bus from Chicago Bus Station to Milwaukee Intermodal Station
- Ave. Duration
- 1h 40m
- Frequency
- 4 times a day
- Estimated price
- $14–23
- Website
- Greyhound
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Booking & Getting There
Jackson to Winona bus services, operated by Greyhound USA, arrive at Memphis Bus Station.
Jackson to Winona train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Jackson to Winona is 930 miles. It takes approximately 16h 26m to drive from Jackson to Winona.
Book your Jackson to Winona train tickets online with Omio.
Book your Jackson to Winona bus tickets online with Omio.
There are 24+ hotels available in Winona.





