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

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There are 13 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 26m
    $76–297

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

    cheapest
    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 26m
    $58–310

  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 50m
    $115–209

  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 55m
    $248–558

  5. Drive 790.6 mi

    1. Drive from Chicago to Middletowncar car 790.6 mi
    13h 32m
    $145–209

  6. 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 4m
    $88–500

  7. 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 22m
    $62–303

  8. Fly Chicago Midway International Airport to Newark Liberty International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Newark Liberty International Airport (EWR)plane plane MDW - EWR
    2. Take the train from Newark Airport Railroad Station to Middletown Njtrain train
    5h 4m
    $90–417

  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 49m
    $108–1,174

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

    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 38m
    $460–645

  11. 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 Airport Terminal Bbus bus
    3. Take the train from Newark Airport Railroad Station to Middletown Njtrain train
    8h 32m
    $126–407

  12. Bus, train via Toledo

    1. Take the bus from Chicago Bus Station to Toledo Bus Stopbus bus
    2. Take the bus from Toledo Bus Stop to Newark Penn Stationbus bus
    3. Take the train from Newark Penn Station to Middletown Njtrain train
    22h 20m
    $125–269

  13. 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 33m
    $292–651

Chicago to Middletown by bus and train

Calendar7Weekly Services
Duration20h 50mAverage Duration
Ticket$115Cheapest Price
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Questions & Answers

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 55m.

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