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How to get fromMontauk to Chicagoby train, plane, bus (Flixbus), train (Amtrak), car, ferry, or bus (Greyhound)

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There are 10 ways to get from Montauk to Chicago by train, plane, bus (Flixbus), train (Amtrak), car, ferry, or bus (Greyhound)

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 Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Montauk to Jamaicatrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 30m
    $180–617

  2. Ferry, train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the ferry from Montauk to New Londonferry ferry
    2. Take the train from New London to Providencetrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    9h 25m
    $139–452

  3. Bus

    1. Take the bus from Montauk Village to Hudson Yardsbus bus Westbound
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    21h 21m
    $164–290

  4. Train

    1. Take the train from Montauk to New York Penn Stationtrain train Montauk Branch
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    23h 21m
    $338–715

  5. Drive 905.1 mi

    1. Drive from Montauk to Chicagocar car 905.1 mi
    15h 39m
    $166–239

  6. Ferry, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the ferry from Montauk to New Londonferry ferry
    2. Take the train from New London to Providencetrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    8h 54m
    $154–502

  7. Ferry, train, train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the ferry from Montauk to New Londonferry ferry
    2. Take the train from New London to New Haventrain train
    3. Take the train from New Haven to Windsor Lockstrain train
    4. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    9h 17m
    $152–509

  8. Ferry, train, train to Bradley International Airport, fly to Chicago O'Hare International Airport

    1. Take the ferry from Montauk to New Londonferry ferry
    2. Take the train from New London to New Haventrain train
    3. Take the train from New Haven to Windsor Lockstrain train
    4. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    9h 51m
    $142–449

  9. Ferry, train to Tweed-New Haven Airport, fly to Chicago O'Hare International Airport

    1. Take the ferry from Montauk to New Londonferry ferry
    2. Take the train from New London to New Haventrain train
    3. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane plane HVN - ORD
    8h 37m
    $237–574

  10. Bus via Baltimore

    1. Take the bus from Montauk to 3 Av & E 42 Stbus bus
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    26h 48m
    $194–430

Montauk to Chicago by train

Calendar3Weekly Trains
Duration23h 21mAverage Duration
Ticket$338Cheapest Price
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Questions & Answers

Map of how to get from Montauk to Chicago.ExpandLaunch map view
  • Distance: 848.3 mi
  • Duration: 7h 30m

What companies run services between Montauk, NY, USA and Chicago, IL, USA?

You can take a bus from Montauk Village to Chicago Bus Station via Hudson Yards and New York Midtown in around 21h 21m. Alternatively, you can take a train from Montauk to Chicago Union Station via Penn Station and Ny Moynihan Train Hall At Penn Station in around 23h 21m.

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