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

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There are 11 ways to get from Montauk to Chicago by train, plane, bus, bus (Flixbus), 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 36m
    $230–717

  2. Ferry, train, train to Bradley International 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 New Haventrain train
    3. Take the train from New Haven to Hartford Amtrak Stationtrain train
    4. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    10h 10m
    $153–488

  3. Bus, train

    1. Take the bus from Montauk Village to Islip Airport Connectionbus bus
    2. Take the train from Ronkonkoma to New York Penn Stationtrain train
    3. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train
    24h 11m
    $541–952

  4. 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 N2640 / ...
    24h 51m
    $184–274

  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 59m
    $184–692

  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 Hartford Amtrak Stationtrain train
    4. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    9h 36m
    $178–608

  8. Ferry, train to Theodore Francis Green State 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 Providencetrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    9h 25m
    $164–532

  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 28m
    $178–503

  10. Train to Laguardia Airport, fly to General Mitchell International Airport, train

    1. Take the train from Montauk to Jamaicatrain train
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    10h 10m
    $215–951

  11. 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
    27h 39m
    $209–345

Laguardia Airport (LGA) to Chicago Midway International Airport (MDW) flights

Calendar66Weekly Planes
Duration2h 30mAverage Duration
Ticket$106Cheapest Price
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Comparing Your Travel Options

Map of how to get from Montauk to Chicago.ExpandLaunch map view
  • Distance: 848.3 mi
  • Duration: 7h 36m

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 24h 51m.

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