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How to get fromChicago to Middletownby plane, train, bus, train (Amtrak), or car

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There are 12 ways to get from Chicago to Middletown by plane, train, bus, train (Amtrak), 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 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 Newark Airport Railroad Station to Middletown Njtrain train
    5h 33m
    $146–887

  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 White Plains to Grand Central Terminaltrain train
    3. Take the train from New York Penn Station to Middletown Njtrain train
    8h 54m
    $104–495

  3. Bus, train

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus bus FlixBus N2640 / ...
    2. Take the train from Newark Penn Station to Middletown Njtrain train Njcl / ...
    20h 52m
    $139–234

  4. Train via New York

    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 Middletown Njtrain train Njcl / ...
    21h 57m
    $254–575

  5. Drive  790.5 mi

    1. Drive from Chicago to Middletowncar car 790.5 mi
    13h 32m
    $145–209

  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 New York Penn Station to Middletown Njtrain train
    6h 23m
    $138–580

  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 New York Penn Station to Middletown Njtrain train
    6h 9m
    $208–680

  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 New York Penn Station to Middletown Njtrain train
    6h 28m
    $328–893

  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 Newark Penn Station to Middletown Njtrain train
    6h 50m
    $166–994

  10. Fly Chicago O'Hare International Airport to Lehigh Valley International Airport, bus, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Lehigh Valley International Airport (ABE)plane plane ORD - ABE
    2. Take the bus from Lehigh Valley International Airport Trans Bridge Bus Stop to Newark Airportbus bus
    3. Take the train from Newark Airport Railroad Station to Middletown Njtrain train
    8h 37m
    $148–455

  11. Bus, train 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 train from New York Penn Station to Middletown Njtrain train
    24h 19m
    $170–336

  12. Train

    1. Take the train from Chicago Union Station to Newark Penn Stationtrain train Cardinal
    2. Take the train from Newark Penn Station to Middletown Njtrain train Njcl / ...
    28h 35m
    $299–671

Chicago to Middletown by bus and train

Calendar14Weekly Services
Duration20h 52mAverage Duration
Ticket$139Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Middletown.ExpandLaunch map view
  • Distance: 765.1 mi
  • Duration: 5h 33m

What companies run services between Chicago, IL, USA and Middletown, Monmouth County, NJ, USA?

You can take a train from Chicago Union Station to Middletown Nj via Ny Moynihan Train Hall At Penn Station and New York Penn Station in around 21h 57m.

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