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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 train
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    5h 30m
    $76–316

  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 train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 39m
    $58–276

  3. Train, bus

    1. Take the train from Middletown Nj to Newark Penn Stationtrain train Njcl / ...
    2. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus FlixBus N2640
    21h 45m
    $98–166

  4. Train via Ossining

    1. Take the train from Middletown Nj to New York Penn Stationtrain train
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Croton-Harmon Amtrak Stationtrain train
    3. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train
    22h 54m
    $140–423

  5. Drive 789.7 mi

    1. Drive from Middletown to Chicagocar car 789.7 mi
    13h 35m
    $145–209

  6. Train to Newark Liberty International Airport, fly to Chicago Midway International Airport

    1. Take the train from Middletown Nj to Newark Airport Railroad Stationtrain train
    2. Fly from Newark Liberty International Airport (EWR) to Chicago Midway International Airport (MDW)plane plane EWR - MDW
    5h 19m
    $96–426

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

    1. Take the train from Middletown Nj to New York Penn Stationtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 23m
    $93–496

  8. 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 train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 40m
    $768–1,042

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

    1. Take the train from Middletown Nj to Newark Penn Stationtrain train
    2. Take the train from Newark Penn Station to 30th Street Stationtrain train
    3. Fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW)plane plane PHL - MDW
    7h 15m
    $101–1,101

  10. Train, bus via Toledo

    1. Take the train from Middletown Nj to Newark Penn Stationtrain train
    2. Take the bus from Newark Penn Station to Toledo Bus Stopbus bus
    3. Take the bus from Toledo Bus Stop to Chicago Bus Stationbus bus
    24h 5m
    $111–251

  11. Train

    1. Take the train from Middletown Nj to Newark Penn Stationtrain train Njcl / ...
    2. Take the train from Newark Penn Station to Chicago Union Stationtrain train Cardinal
    30h 3m
    $133–366

Middletown to Chicago by train and bus

Calendar7Weekly Services
Duration21h 45mAverage Duration
Ticket$98Cheapest 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 54m.

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