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

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There are 11 ways to get from Chicago to Middle Island by plane, train, bus, train (Amtrak), bus (Flixbus), car, or car ferry

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, line 58 bus

    best
    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 13m
    $146–731

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

    cheapest
    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 13m
    $84–337

  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 Brentwoodtrain train Ronkonkoma Branch
    23h 29m
    $302–623

  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
    $167–302

  5. Drive 850.3 mi

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

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

    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 35m
    $96–371

  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 1m
    $128–392

  8. Fly Chicago O'Hare International Airport to Tweed-New Haven Airport, car ferry

    1. Fly from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN)plane plane ORD - HVN
    2. Take the car ferry from Bridgeport to Port Jeffersoncarferry car ferry
    7h 11m
    $198–574

  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 7m
    $190–1,437

  10. 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 Grand Central Terminal to Brentwoodtrain train
    4. Take the bus from Brentwood LIRR to Middle Country Rd/Yaphank Middle Island Rdbus bus
    10h 40m
    $120–522

  11. 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 10m
    $171–362

Chicago to Middle Island by train and bus

Calendar10Weekly Services
Duration23h 29mAverage Duration
Ticket$302Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Middle Island.ExpandLaunch map view
  • Distance: 797.4 mi
  • Duration: 7h 13m

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

You can take a train from Chicago Union Station to Middle Country Rd/Yaphank Middle Island Rd via Ny Moynihan Train Hall At Penn Station, New York Penn Station, Brentwood, and Brentwood LIRR in around 23h 29m. 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.

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