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How to get fromChicago to Middle Islandby plane, train, bus, train (Amtrak), bus (Flixbus) or car

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There are 10 ways to get from Chicago to Middle Island by plane, train, bus, train (Amtrak), bus (Flixbus), or car

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 O'Hare International Airport to John F. Kennedy International Airport, train, line 58 bus

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the train from Jamaica to Brentwoodtrain train
    3. Take the bus from Brentwood LIRR to Middle Country Rd/Yaphank Middle Island Rdbus bus
    7h 23m
    $68–297

  2. Fly Chicago O'Hare International Airport to Laguardia Airport, train, line 58 bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from Woodside to Brentwoodtrain train
    3. Take the bus from Brentwood LIRR to Middle Country Rd/Yaphank Middle Island Rdbus bus
    7h 47m
    $66–312

  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 Ronkonkomatrain train Ronkonkoma Branch
    22h 11m
    $412–779

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640
    2. Take the bus from 41st St bet 3rd & Lex to Old Country Rd/Tanger Mall Drbus bus North Fork
    25h 15m
    $169–313

  5. Drive 850.3 mi

    1. Drive from Chicago to Middle Islandcar car 850.3 mi
    14h 24m
    $156–225

  6. Fly Chicago Midway International Airport to Laguardia Airport, train, line 58 bus

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from Woodside to Brentwoodtrain train
    3. Take the bus from Brentwood LIRR to Middle Country Rd/Yaphank Middle Island Rdbus bus
    7h 21m
    $100–512

  7. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, train, line 58 bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from New York Penn Station to Brentwoodtrain train
    3. Take the bus from Brentwood LIRR to Middle Country Rd/Yaphank Middle Island Rdbus bus
    8h 6m
    $86–332

  8. Fly Chicago O'Hare International Airport to Westchester County Airport, train, line 58 bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from White Plains to Grand Central Terminaltrain train
    3. Take the train from Jamaica to Brentwoodtrain train
    4. Take the bus from Brentwood LIRR to Middle Country Rd/Yaphank Middle Island Rdbus bus
    10h 15m
    $468–652

  9. Fly Chicago Midway International Airport to Philadelphia International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL)plane plane MDW - PHL
    2. Take the train from 30th Street Station to Ny Moynihan Train Hall At Penn Stationtrain train
    3. Take the train from New York Penn Station to Brentwoodtrain train
    9h 15m
    $126–1,187

  10. Bus, train

    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 train from New York Penn Station to Brentwoodtrain train
    25h 19m
    $197–413

Chicago to Middle Island by bus and foot

Calendar7Weekly Services
Duration25h 15mAverage Duration
Ticket$169Cheapest Price
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Questions & Answers

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

You can take a train from Chicago Union Station to Middle Island via Ny Moynihan Train Hall At Penn Station, New York Penn Station, and Ronkonkoma in around 22h 11m. Alternatively, you can take a bus from Chicago Bus Station to Middle Country Rd/Tudor Ln via New York Midtown, W 42 St/Broadway, E 42 St/Lexington Av, 41st St bet 3rd & Lex, Old Country Rd/Tanger Mall Dr, and Riverhead LIRR in around 25h 15m.

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