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How to get fromChicago to Middletown Nyby plane, train, bus, bus (Flixbus, Greyhound), car, or train (Amtrak)

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There are 14 ways to get from Chicago to Middletown Ny by plane, train, bus, bus (Flixbus, Greyhound), car, or train (Amtrak)

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 Newark Liberty International Airport, train

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Secaucus Lower Level to Middletown Nytrain train
    7h 1m
    $144–906

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the bus from Martine Ave. & Court St. to Palisades Center Dr. Lot Jbus bus
    3. Take the bus from Palisades Center Dr. Lot J to Hallett Pl. & Chestnet St. Suffernbus bus
    4. Take the train from Suffern to Middletown Nytrain train
    9h 40m
    $94–490

  3. Train, bus

    1. Take the train from Chicago Union Station to Syracuse Regional Transportation Centertrain train Lake Shore Limited
    2. Take the bus from Syracuse to Middletownbus bus Adt A143 / ...
    18h 4m
    $206–508

  4. Bus

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus bus
    2. Take the bus from Newark Penn Station to Port Authority Bus Terminalbus bus 108
    3. Take the bus from New York to Middletownbus bus
    23h 7m
    $164–313

  5. Drive  777.8 mi

    1. Drive from Chicago to Middletown Nycar car 777.8 mi
    12h 51m
    $142–205

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from Secaucus Lower Level to Middletown Nytrain train
    7h 25m
    $140–596

  7. Fly Chicago Midway International Airport to Laguardia Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from Secaucus Lower Level to Middletown Nytrain train
    7h 11m
    $210–696

  8. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    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 Secaucus Lower Level to Middletown Nytrain train
    7h 30m
    $330–909

  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 Newark Penn Stationtrain train
    3. Take the train from Secaucus Lower Level to Middletown Nytrain train
    8h 8m
    $168–1,013

  10. Fly Chicago Midway International Airport to Albany County Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    2. Take the bus from Albany to Newburghbus bus
    3. Take the bus from Newburgh ShortLine Transportation Center to Galleria Dr - Galleria Mallbus bus
    9h 30m
    $180–883

  11. Fly Chicago O'Hare International Airport to Wilkes-Barre/Scranton International Airport, bus, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Wilkes-Barre/Scranton International Airport (AVP)plane plane ORD - AVP
    2. Take the bus from Scranton to Newark Penn Stationbus bus
    3. Take the train from Secaucus Lower Level to Middletown Nytrain train
    9h 41m
    $118–486

  12. 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 Secaucus Lower Level to Middletown Nytrain train Mnbnp
    22h 59m
    $256–591

  13. Bus, train

    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 Port Authority Bus Terminal to Hoboken Terminal Lane 6bus bus 126
    4. Take the train from Hoboken to Middletown Nytrain train
    25h 32m
    $176–365

  14. Train via Newark

    1. Take the train from Chicago Union Station to Newark Penn Stationtrain train Cardinal
    2. Take the train from Secaucus Lower Level to Middletown Nytrain train Mnbnp
    29h 53m
    $301–690

Chicago to Middletown Ny by train

Calendar10Weekly Trains
Duration22h 59mAverage Duration
Ticket$256Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Middletown Ny.ExpandLaunch map view
  • Distance: 810.9 mi
  • Duration: 7h 1m

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

You can take a bus from Chicago Bus Station to Middletown Ny via Newark Penn Station, Port Authority Bus Terminal, New York, and Middletown in around 23h 7m. Alternatively, you can take a train from Chicago Union Station to Middletown Ny via Ny Moynihan Train Hall At Penn Station, New York Penn Station, and Secaucus Lower Level in around 22h 59m.

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