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How to get fromWinona to Bostonby train, plane, train (Amtrak), bus (Greyhound, Flixbus), car, or bus

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There are 8 ways to get from Winona to Boston by train, plane, train (Amtrak), bus (Greyhound, Flixbus), car, 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.

  1. Train to Minneapolis–Saint Paul International Airport, fly to Theodore Francis Green State Airport, train

    best
    1. Take the train from Winona to St. Paul-Minneapolistrain train
    2. Fly from Minneapolis–Saint Paul International Airport (MSP) to Theodore Francis Green State Airport (PVD)plane plane MSP - PVD
    3. Take the train from TF Green Airport to South Stationtrain train
    9h 21m
    $147–505

  2. Train (Amtrak)

    1. Take the train from Winona to Chicago Union Stationtrain train Empire Builder / ...
    2. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    28h 46m
    $719–1,159

  3. Bus

    1. Take the bus from Winona St. University to Milwaukeebus bus
    2. Take the bus from Milwaukee Intermodal Station to Chicago Bus Stationbus bus
    3. Take the bus from Chicago Bus Station to New York Midtownbus bus
    4. Take the bus from New York Midtown to Bostonbus bus
    33h 49m
    $255–397

  4. Drive  1,284.6 mi

    1. Drive from Winona to Bostoncar car 1,284.6 mi
    21h 49m
    $213–307

  5. Train to Minneapolis–Saint Paul International Airport, fly to Bradley International Airport, bus

    1. Take the train from Winona to St. Paul-Minneapolistrain train
    2. Fly from Minneapolis–Saint Paul International Airport (MSP) to Bradley International Airport (BDL)plane plane MSP - BDL
    3. Take the bus from Hartford Union Station to Bostonbus bus
    10h 9m
    $266–1,068

  6. Train to Minneapolis–Saint Paul International Airport, fly to Laguardia Airport, train

    1. Take the train from Winona to St. Paul-Minneapolistrain train
    2. Fly from Minneapolis–Saint Paul International Airport (MSP) to Laguardia Airport (LGA)plane plane MSP - LGA
    3. Take the train from Ny Moynihan Train Hall At Penn Station to Bostontrain train
    11h 51m
    $341–1,095

  7. Train to Chicago Midway International Airport, fly to Manchester Airport, bus

    1. Take the train from Winona to Chicago Union Stationtrain train
    2. Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane plane MDW - MHT
    3. Take the bus from Boston Manchester Airport to Bostonbus bus
    12h 19m
    $280–878

  8. Bus, train

    1. Take the bus from Winona St. University to Madisonbus bus
    2. Take the bus from 250 N. Lake St - Madison UW Campus to W Jackson Blvd, after S Clinton Stbus bus
    3. Take the train from Chicago Union Station to Bostontrain train
    30h 58m
    $621–1,021

Winona to Boston by train (Amtrak)

Calendar7Weekly Trains
Duration28h 46mAverage Duration
Ticket$719Cheapest Price
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Comparing Your Travel Options

Map of how to get from Winona to Boston.ExpandLaunch map view
  • Distance: 1,275.8 mi
  • Duration: 9h 21m

What companies run services between Winona, MN, USA and Boston, MA, USA?

You can take a train from Winona to Boston via Chicago Union Station in around 28h 46m. Alternatively, you can take a bus from Winona St. University to Boston via Milwaukee, Milwaukee Intermodal Station, Chicago Bus Station, and New York Midtown in around 33h 49m.

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