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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 11 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 6m
    $120–568

  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 New York Penn Station to Montauktrain train
    10h 30m
    $114–486

  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
    23h 43m
    $242–557

  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 48m
    $149–279

  5. Drive 905.4 mi

    1. Drive from Chicago to Montaukcar car 905.4 mi
    15h 39m
    $166–239

  6. Fly Chicago Midway International Airport to Boston Logan Airport, train, ferry

    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    2. Take the train from Boston to New Londontrain train
    3. Take the ferry from New London to Montaukferry ferry
    9h 20m
    $202–979

  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
    9h 31m
    $154–767

  8. 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
    9h 52m
    $172–1,103

  9. 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 1m
    $124–607

  10. 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
    10h 22m
    $138–883

  11. Bus via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the bus from 40th & Lex to Montaukbus bus
    26h 5m
    $187–374

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

Calendar53Weekly Planes
Duration2h 22mAverage Duration
Ticket$90Cheapest Price
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Questions & Answers

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 23h 43m. Alternatively, you can take a bus from Chicago Bus Station to Montauk via New York Midtown, W 34 St/7 Av, E 34 St/5 Av, and 40th & Lex in around 24h 48m.

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