There are 10 ways to get from Boston to Winona by ferry, plane, taxi, train (Amtrak), bus (Flixbus, Greyhound), 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.
Ferry to Boston Logan Airport, fly to La Crosse, taxi
best- Take the ferry from Long Wharf to Logan Airport Ferry Terminalferry
- Fly from Boston Logan Airport (BOS) to La Crosse (LSE)plane BOS - LSE
- Take the taxi from La-Crosse-Airport-LSE to Winonataxi
7h 31m$169–640Ferry to Boston Logan Airport, fly to Rochester, bus
cheapest- Take the ferry from Long Wharf to Logan Airport Ferry Terminalferry
- Fly from Boston Logan Airport (BOS) to Rochester (RST)plane BOS - RST
- Take the bus from Rochester to Winona St. Universitybus
9h 52m$127–635Train (Amtrak)
- Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
- Take the train from Chicago Union Station to Winonatrain Empire Builder / ...
28h 51m$359–927Bus
- Take the bus from Boston to New York Midtownbus
- Take the bus from New York Midtown to Chicago Bus Stationbus
- Take the bus from Chicago Bus Station to Milwaukee Intermodal Stationbus
- Take the bus from Milwaukee to Winona St. Universitybus
34h 10m$255–386Drive 1,284.5 mi
- Drive from Boston to Winonacar 1,284.5 mi
21h 46m$235–339Ferry to Boston Logan Airport, fly to Minneapolis–Saint Paul International Airport, train
- Take the ferry from Long Wharf to Logan Airport Ferry Terminalferry
- Fly from Boston Logan Airport (BOS) to Minneapolis–Saint Paul International Airport (MSP)plane BOS - MSP
- Take the train from St. Paul-Minneapolis to Winonatrain
8h 35m$434–1,088Ferry to Boston Logan Airport, fly to Dane County Regional Airport-Truax Field, bus
- Take the ferry from Long Wharf to Logan Airport Ferry Terminalferry
- Fly from Boston Logan Airport (BOS) to Dane County Regional Airport-Truax Field (MSN)plane BOS - MSN
- Take the bus from Madison to Winona St. Universitybus
9h 55m$186–827Train to Theodore Francis Green State Airport, fly to Minneapolis–Saint Paul International Airport, train
- Take the train from South Station to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Minneapolis–Saint Paul International Airport (MSP)plane PVD - MSP
- Take the train from St. Paul-Minneapolis to Winonatrain
9h 31m$170–794Ferry to Boston Logan Airport, fly to General Mitchell International Airport, train
- Take the ferry from Long Wharf to Logan Airport Ferry Terminalferry
- Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane BOS - MKE
- Take the train from Milwaukee to Winonatrain
9h 38m$716–2,084Train, bus
- Take the train from Boston 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
31h 4m$344–827
Boston to Winona by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Boston to Winona is to drive which costs $230 - $340 and takes 21h 46m.
The fastest way to get from Boston to Winona is to ferry and fly and taxi which takes 7h 31m and costs $160 - $650.
No, there is no direct bus from Boston to Winona. However, there are services departing from Boston and arriving at Winona St. University via New York Midtown, Chicago Bus Station and Milwaukee. The journey, including transfers, takes approximately 34h 10m.
No, there is no direct train from Boston to Winona. However, there are services departing from Boston and arriving at Winona via Chicago Union Station. The journey, including transfers, takes approximately 28h 51m.
The distance between Boston and Winona is 1061 miles. The road distance is 1292 miles.
The best way to get from Boston to Winona without a car is to train which takes 28h 51m and costs $350 - $950.
It takes approximately 7h 31m to get from Boston to Winona, including transfers.
Boston to Winona bus services, operated by Flixbus USA, depart from Boston station.
Boston to Winona train services, operated by Amtrak, depart from Boston station.
The best way to get from Boston to Winona is to train which takes 28h 51m and costs $350 - $950. Alternatively, you can bus, which costs $250 - $390 and takes 34h 10m.
What companies run services between Boston, MA, USA and Winona, MN, USA?
You can take a train from Boston to Winona via Chicago Union Station in around 28h 51m. Alternatively, you can take a bus from Boston to Winona St. University via New York Midtown, Chicago Bus Station, Milwaukee Intermodal Station, and Milwaukee in around 34h 10m.
- Website
- delta.com
Flights from Boston Logan Airport to Minneapolis–Saint Paul International Airport
- Ave. Duration
- 3h 14m
- When
- Every day
- Estimated price
- $130–650
Flights from Boston Logan Airport to Minneapolis–Saint Paul International Airport via Dane County Regional Airport-Truax Field
- Ave. Duration
- 5h 19m
- When
- Every day
- Estimated price
- $130–650
Flights from Boston Logan Airport to Minneapolis–Saint Paul International Airport via General Mitchell International Airport
- Ave. Duration
- 5h 45m
- When
- Every day
- Estimated price
- $130–650
Flights from Boston Logan Airport to Rochester via Minneapolis–Saint Paul International Airport
- Ave. Duration
- 6h 35m
- When
- Every day
- Estimated price
- $110–550
Flights from Boston Logan Airport to Dane County Regional Airport-Truax Field
- Ave. Duration
- 2h 48m
- When
- Every day
- Estimated price
- $140–750
Flights from Boston Logan Airport to Dane County Regional Airport-Truax Field via Detroit
- Ave. Duration
- 4h 49m
- When
- Every day
- Estimated price
- $140–750
Flights from Boston Logan Airport to Dane County Regional Airport-Truax Field via Reagan Washington
- Ave. Duration
- 5h 8m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $160–800
Flights from Boston Logan Airport to Dane County Regional Airport-Truax Field via Minneapolis–Saint Paul International Airport
- Ave. Duration
- 5h 23m
- When
- Every day
- Estimated price
- $180–900
Flights from Theodore Francis Green State Airport to Minneapolis–Saint Paul International Airport
- Ave. Duration
- 3h 4m
- When
- Every day
- Estimated price
- $130–700
Flights from Theodore Francis Green State Airport to Minneapolis–Saint Paul International Airport via Detroit
- Ave. Duration
- 5h 11m
- When
- Every day
- Estimated price
- $130–700
Flights from Boston Logan Airport to General Mitchell International Airport
- Ave. Duration
- 2h 43m
- When
- Every day
- Estimated price
- $120–700
Flights from Boston Logan Airport to General Mitchell International Airport via Detroit
- Ave. Duration
- 4h 29m
- When
- Every day
- Estimated price
- $120–700
Flights from Boston Logan Airport to General Mitchell International Airport via New York La Guardia
- Ave. Duration
- 4h 56m
- When
- Monday to Friday
- Estimated price
- $130–700
- Website
- southwest.com
Flights from Theodore Francis Green State Airport to Minneapolis–Saint Paul International Airport via Chicago Midway
- Ave. Duration
- 5h 25m
- When
- Monday, Thursday, Friday, Sunday, and Saturday
- Estimated price
- $140–700
Flights from Theodore Francis Green State Airport to Minneapolis–Saint Paul International Airport via Baltimore
- Ave. Duration
- 5h 38m
- When
- Saturday to Wednesday
- Estimated price
- $140–700
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago Midway
- Ave. Duration
- 4h 37m
- When
- Tuesday to Saturday
- Estimated price
- $130–700
Flights from Boston Logan Airport to General Mitchell International Airport via Baltimore
- Ave. Duration
- 4h 43m
- When
- Monday, Thursday, Friday, Sunday, and Saturday
- Estimated price
- $140–700
- Website
- aa.com
Flights from Boston Logan Airport to La Crosse via Chicago O'Hare
- Ave. Duration
- 5h 35m
- When
- Every day
- Estimated price
- $100–550
Flights from Boston Logan Airport to La Crosse via Buffalo, Chicago O'Hare
- Ave. Duration
- 10h 54m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $100–550
Flights from Boston Logan Airport to Rochester via Chicago O'Hare
- Ave. Duration
- 6h 12m
- When
- Every day
- Estimated price
- $100–550
Flights from Boston Logan Airport to Dane County Regional Airport-Truax Field
- Ave. Duration
- 2h 58m
- When
- Every day
- Estimated price
- $140–750
Flights from Boston Logan Airport to Dane County Regional Airport-Truax Field via New York La Guardia
- Ave. Duration
- 4h 52m
- When
- Monday to Friday
- Estimated price
- $150–750
Flights from Boston Logan Airport to Dane County Regional Airport-Truax Field via Philadelphia
- Ave. Duration
- 5h 14m
- When
- Every day
- Estimated price
- $150–800
Flights from Boston Logan Airport to General Mitchell International Airport via Philadelphia
- Ave. Duration
- 4h 58m
- When
- Monday, Wednesday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $130–700
- Website
- united.com
Flights from Boston Logan Airport to Dane County Regional Airport-Truax Field via Chicago O'Hare
- Ave. Duration
- 5h 8m
- When
- Every day
- Estimated price
- $140–750
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago O'Hare
- Ave. Duration
- 5h 1m
- When
- Every day
- Estimated price
- $130–700
- Website
- suncountry.com
Flights from Boston Logan Airport to Minneapolis–Saint Paul International Airport
- Ave. Duration
- 3h 9m
- When
- Monday, Thursday, Tuesday, Wednesday, Saturday, and Sunday
- Estimated price
- $130–650
- Website
- jetblue.com
Flights from Boston Logan Airport to General Mitchell International Airport
- Ave. Duration
- 2h 32m
- When
- Every day
- Estimated price
- $120–700
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Boston to Chicago Union Station
- Ave. Duration
- 22h 22m
- Frequency
- Once daily
- Estimated price
- $270–750
- Website
- Amtrak
Train from Chicago Union Station to Winona
- Ave. Duration
- 5h 29m
- Frequency
- 3 times a day
- Estimated price
- $80–220
- Website
- Amtrak
Train from St. Paul-Minneapolis to Winona
- Ave. Duration
- 2h 4m
- Frequency
- 3 times a day
- Estimated price
- $28–75
- Website
- Amtrak
Train from St. Paul-Minneapolis to Winona
- Ave. Duration
- 2h 4m
- Frequency
- 3 times a day
- Estimated price
- $28–75
- Website
- Amtrak
Train from Milwaukee to Winona
- Ave. Duration
- 3h 49m
- Frequency
- 3 times a day
- Estimated price
- $60–160
- Website
- Amtrak
Train from Boston to Chicago Union Station
- Ave. Duration
- 22h 22m
- Frequency
- Once daily
- Estimated price
- $270–750
- Website
- Amtrak
Train from South Station to TF Green Airport
- Ave. Duration
- 1h 30m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Boston to New York Midtown
- Ave. Duration
- 4h 20m
- Frequency
- Hourly
- Estimated price
- $30–50
- Schedules at
- Flixbus USA
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 20h 25m
- Frequency
- Twice daily
- Estimated price
- $150–230
- Schedules at
- Flixbus USA
Bus from Chicago Bus Station to Milwaukee Intermodal Station
- Ave. Duration
- 1h 55m
- Frequency
- 3 times a day
- Estimated price
- $13–21
- Schedules at
- Flixbus USA
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- 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
- Phone
- +1-858-800-8898
- Website
- jeffersonlines.com
Bus from Milwaukee to Winona St. University
- Ave. Duration
- 4h 45m
- Frequency
- Once daily
- Estimated price
- $60–85
- Book at
- Jefferson Lines
- Adult
- $60–85
Bus from Rochester to Winona St. University
- Ave. Duration
- 55 min
- Frequency
- Once daily
- Estimated price
- $22–35
- Book at
- Jefferson Lines
- Adult
- $22–35
Bus from Madison to Winona St. University
- Ave. Duration
- 3h 25m
- Frequency
- Once daily
- Estimated price
- $40–65
- Book at
- Jefferson Lines
- Adult
- $40–65
Bus from Madison to Winona St. University
- Ave. Duration
- 3h 25m
- Frequency
- Once daily
- Estimated price
- $40–65
- Book at
- Jefferson Lines
- Adult
- $40–65
- Phone
- +1 (866) 912 - 6224
- questions@coachusa.com
- Website
- Rockland Coaches
Bus from W Jackson Blvd, after S Clinton St to 250 N. Lake St - Madison UW Campus
- Ave. Duration
- 3h 40m
- Frequency
- Hourly
- Estimated price
- $25–55
- Schedules at
- Rockland Coaches
- Adult
- $25–55
Ferry from Long Wharf to Logan Airport Ferry Terminal
- Ave. Duration
- 20 min
- Frequency
- Hourly
- Estimated price
- $3–10
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $3–10
Ferry from Long Wharf to Logan Airport Ferry Terminal
- Ave. Duration
- 20 min
- Frequency
- Hourly
- Estimated price
- $3–10
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $3–10
Ferry from Long Wharf to Logan Airport Ferry Terminal
- Ave. Duration
- 20 min
- Frequency
- Hourly
- Estimated price
- $3–10
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $3–10
Ferry from Long Wharf to Logan Airport Ferry Terminal
- Ave. Duration
- 20 min
- Frequency
- Hourly
- Estimated price
- $3–10
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $3–10
Ferry from Long Wharf to Logan Airport Ferry Terminal
- Ave. Duration
- 20 min
- Frequency
- Hourly
- Estimated price
- $3–10
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $3–10
Want to know more about travelling around United States
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Booking & Getting There
Boston to Winona bus services, operated by Flixbus USA, arrive at New York Midtown station.
Winona is 1h behind Boston. It is currently 12:16 PM in Boston and 11:16 AM in Winona.
Boston to Winona train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Boston to Winona is 1292 miles. It takes approximately 21h 46m to drive from Boston to Winona.
Book your Boston to Winona train tickets online with Omio.
Book your Boston to Winona bus tickets online with Omio.
There are 24+ hotels available in Winona.












