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How to get fromBoston to Winthrop Harborby plane, train, train (Amtrak), bus (Flixbus), car, or bus

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There are 9 ways to get from Boston to Winthrop Harbor by plane, train, train (Amtrak), bus (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. Fly Boston Logan Airport to Chicago Midway International Airport, train

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    2. Take the train from Chicago OTC to Winthrop Harbortrain train
    5h 48m
    $92–411

  2. Bus to Manchester Airport, fly to Chicago O'Hare International Airport, train

    cheapest
    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)plane plane MHT - ORD
    3. Take the train from Clybourn to Winthrop Harbortrain train
    8h 12m
    $90–408

  3. Train

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    2. Take the train from Chicago OTC to Winthrop Harbortrain train Up-N
    25h
    $343–680

  4. Bus

    1. Take the bus from Boston to New York Midtownbus bus
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    3. Take the bus from Chicago Bus Station to Milwaukee Mitchell Airportbus bus
    4. Take the bus from Mitchell Airport to Metro Train Station - 13th Avenue and 54th Streetbus bus
    28h 5m
    $196–326

  5. Drive 1,027.4 mi

    1. Drive from Boston to Winthrop Harborcar car 1,027.4 mi
    17h 53m
    $188–271

  6. Fly Boston Logan Airport to General Mitchell International Airport, bus

    1. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    2. Take the bus from Mitchell Airport to Metro Train Station - 13th Avenue and 54th Streetbus bus
    5h 50m
    $668–3,244

  7. Fly Boston Logan Airport to Chicago O'Hare International Airport, train

    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    2. Take the train from Clybourn to Winthrop Harbortrain train
    6h 8m
    $626–900

  8. Bus to Manchester Airport, fly to Chicago Midway International Airport, train

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    3. Take the train from Chicago OTC to Winthrop Harbortrain train
    7h 43m
    $106–478

  9. Train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport, train

    1. Take the train from South Station to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    3. Take the train from Chicago OTC to Winthrop Harbortrain train
    8h 25m
    $93–409

Boston to Winthrop Harbor by train and bus

Calendar7Weekly Services
Duration25hAverage Duration
Ticket$343Cheapest Price
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Questions & Answers

Map of how to get from Boston to Winthrop Harbor.ExpandLaunch map view
  • Distance: 913.7 mi
  • Duration: 5h 48m

What companies run services between Boston, MA, USA and Winthrop Harbor, IL, USA?

You can take a train from Boston to Winthrop Harbor via Chicago Union Station, Clinton & Quincy, Washington & Canal, and Chicago OTC in around 25h. Alternatively, you can take a bus from Boston to Winthrop Harbor via New York Midtown, Chicago Bus Station, Milwaukee Mitchell Airport, Mitchell Airport, Metro Train Station - 13th Avenue and 54th Street, and Kenosha in around 28h 5m.

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