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How to get fromMiddletown to Chicagoby train, plane, bus, train (Amtrak) or car

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There are 11 ways to get from Middletown to Chicago by train, plane, 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. Train to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the train from Middletown Nj to Newark Airport Railroad Stationtrain
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)planeEWR - ORD
    5h 29m
    $81–326

  2. Train to Laguardia Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Middletown Nj to New York Penn Stationtrain
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)planeLGA - ORD
    6h 28m
    $58–286

  3. Train, bus

    1. Take the train from Middletown Nj to Newark Penn StationtrainNjcl / ...
    2. Take the bus from Newark Penn Station to Chicago Bus StationbusFlixBus N2640
    21h 44m
    $93–216

  4. Train via Ossining

    1. Take the train from Middletown Nj to New York Penn Stationtrain
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Croton-Harmon Amtrak Stationtrain
    3. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain
    22h 53m
    $150–438

  5. Drive 789.7 mi

    1. Drive from Middletown to Chicagocar789.7 mi
    13h 26m
    $145–209

  6. Train to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Middletown Nj to New York Penn Stationtrain
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)planeLGA - MDW
    6h 17m
    $83–456

  7. Train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Middletown Nj to New York Penn Stationtrain
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)planeJFK - ORD
    6h 37m
    $818–1,042

  8. Train, train to Philadelphia International Airport, fly to Chicago Midway International Airport

    1. Take the train from Middletown Nj to Newark Penn Stationtrain
    2. Take the train from Newark Penn Station to 30th Street Stationtrain
    3. Fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW)planePHL - MDW
    7h 8m
    $96–1,061

  9. Train to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Middletown Nj to New York Penn Stationtrain
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)planeHPN - ORD
    8h 48m
    $85–404

  10. Train, bus via Toledo

    1. Take the train from Middletown Nj to Newark Penn Stationtrain
    2. Take the bus from Newark Penn Station to Toledo Bus Stopbus
    3. Take the bus from Toledo Bus Stop to Chicago Bus Stationbus
    23h 34m
    $86–226

  11. Train

    1. Take the train from Middletown Nj to Newark Penn StationtrainNjcl / ...
    2. Take the train from Newark Penn Station to Chicago Union StationtrainCardinal
    30h 2m
    $163–566

Middletown to Chicago by train and bus

Calendar7Weekly Services
Duration21h 44mAverage Duration
Ticket$93Cheapest Price
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Questions & Answers

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

You can take a train from Middletown Nj to Chicago Union Station via Penn Station, Ny Moynihan Train Hall At Penn Station, and Croton-Harmon Amtrak Station in around 22h 53m.

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