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How to get fromChicago to Montaukby plane, train, train (Amtrak), bus (Flixbus), car, ferry, or bus (Greyhound)

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There are 10 ways to get from Chicago to Montauk by plane, train, train (Amtrak), 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. Fly Chicago Midway International Airport to Laguardia Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from Jamaica to Montauktrain train
    8h 9m
    $230–718

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from Jamaica to Montauktrain train
    11h 2m
    $126–552

  3. Train

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train Lake Shore Limited / ...
    2. Take the train from New York Penn Station to Montauktrain train Montauk Branch
    24h 29m
    $263–623

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640 / ...
    2. Take the bus from 40th & Lex to Montaukbus bus Montauk-Eastbound / ...
    24h 29m
    $185–302

  5. Drive  905.4 mi

    1. Drive from Chicago to Montaukcar car 905.4 mi
    15h 42m
    $166–239

  6. Fly Chicago O'Hare International Airport to Theodore Francis Green State Airport, train, ferry

    1. Fly from Chicago O'Hare International Airport (ORD) to Theodore Francis Green State Airport (PVD)plane plane ORD - PVD
    2. Take the train from Providence to New Londontrain train
    3. Take the ferry from New London to Montaukferry ferry
    10h 47m
    $126–467

  7. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train, ferry

    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane plane MDW - PVD
    2. Take the train from Providence to New Londontrain train
    3. Take the ferry from New London to Montaukferry ferry
    10h 38m
    $146–577

  8. Fly Chicago O'Hare International Airport to Bradley International Airport, train, ferry

    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the train from Windsor Locks to New Haventrain train
    3. Take the train from New Haven to New Londontrain train
    4. Take the ferry from New London to Montaukferry ferry
    11h 28m
    $160–632

  9. Fly Chicago Midway International Airport to Bradley International Airport, train, ferry

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the train from Windsor Locks to New Haventrain train
    3. Take the train from New Haven to New Londontrain train
    4. Take the ferry from New London to Montaukferry ferry
    11h 15m
    $184–822

  10. Bus via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to New Yorkbus bus
    3. Take the bus from 40th & Lex to Montaukbus bus
    26h 30m
    $203–354

Chicago to Montauk by train

Calendar6Weekly Trains
Duration24h 29mAverage Duration
Ticket$263Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Montauk.ExpandLaunch map view
  • Distance: 848.3 mi
  • Duration: 8h 9m

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

You can take a train from Chicago Union Station to Montauk via Ny Moynihan Train Hall At Penn Station and New York Penn Station in around 24h 29m. Alternatively, you can take a bus from Chicago Bus Station to Montauk via New York Midtown, W 34 St/7 Av, E 34 St/3 Av, and 40th & Lex in around 24h 29m.

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