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How to get fromManchester-by-the-Sea to Chicagoby plane, train (Amtrak), bus (Greyhound), car, train, bus, or bus (Flixbus)

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There are 11 ways to get from Manchester-by-the-Sea to Chicago by plane, train (Amtrak), bus (Greyhound), car, train, bus, or bus (Flixbus)

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

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    5h 46m
    $107–569

  2. Fly Boston Logan Airport to Chicago O'Hare International Airport

    cheapest
    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    6h 3m
    $77–399

  3. Train

    1. Take the train from Manchester to North Stationtrain train Newburyport/Rockport Line
    2. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    24h 23m
    $558–913

  4. Bus via Brook Park (Greyhound)

    1. Take the bus from Boston to Cleveland Bus Stationbus bus Greyhound US0171
    2. Take the bus from Cleveland Bus Station to Chicago Bus Stationbus bus Greyhound US0164
    24h 30m
    $185–299

  5. Drive  1,003 mi

    1. Drive from Manchester-by-the-Sea to Chicagocar car 1,003 mi
    17h 29m
    $172–248

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

    1. Take the train from Manchester to North Stationtrain train
    2. Take the bus from Boston to Boston Manchester Airportbus bus
    3. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    7h 36m
    $104–492

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

    1. Take the train from Manchester to North Stationtrain train
    2. Take the train from Ruggles to TF Green Airporttrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    7h 57m
    $119–583

  8. Train, bus to Manchester Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Manchester to North Stationtrain train
    2. Take the bus from Boston to Boston Manchester Airportbus bus
    3. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)plane plane MHT - ORD
    8h 11m
    $79–362

  9. Train, train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Manchester to North Stationtrain train
    2. Take the train from Ruggles to TF Green Airporttrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    8h 31m
    $89–403

  10. Fly Boston Logan Airport to General Mitchell International Airport, train

    1. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    8h 1m
    $182–853

  11. Bus (Flixbus)

    1. Take the bus from Boston to New York Midtownbus bus FlixBus 2610 / ...
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    27h 53m
    $195–309

Manchester-by-the-Sea to Chicago by train and subway

Calendar7Weekly Services
Duration24h 23mAverage Duration
Ticket$558Cheapest Price
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Comparing Your Travel Options

Map of how to get from Manchester-by-the-Sea to Chicago.ExpandLaunch map view
  • Distance: 893.2 mi
  • Duration: 5h 46m

What companies run services between Manchester-by-the-Sea, MA, USA and Chicago, IL, USA?

Southwest Airlines and Delta fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a train from Manchester to Chicago Union Station via North Station, North Station, Back Bay, and Boston in around 24h 23m.

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Need to know: Greyhound

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