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

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Middletown to Chicago

Rome2Rio compared 12 ways to get from Middletown to Chicago. The best route is Train to Newark Liberty International Airport, fly to Chicago O'Hare International Airport, a distance of 1142.173 km.

  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 31m
    $116–486

  2. Train to Westchester County 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 Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    8h 41m
    $95–454

  3. 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 48m
    $313–639

  4. 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 N2642 / ...
    23h 53m
    $143–246

  5. Drive 789.7 mi

    1. Drive from Middletown to Chicagocar car 789.7 mi
    13h 33m
    $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 train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 12m
    $128–676

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

    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 28m
    $98–356

  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 30m
    $449–892

  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
    6h 43m
    $126–1,224

  10. Train to Newark Liberty International Airport, fly to General Mitchell International Airport, train

    1. Take the train from Middletown Nj to Newark Airport Railroad Stationtrain train
    2. Fly from Newark Liberty International Airport (EWR) to General Mitchell International Airport (MKE)plane plane EWR - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    7h 34m
    $604–900

  11. Train, bus via Baltimore

    1. Take the train from Middletown Nj to New York Penn Stationtrain train
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    25h 7m
    $158–348

  12. 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 26m
    $373–766

Middletown to Chicago by train

Calendar7Weekly Trains
Duration22h 48mAverage Duration
Ticket$313Cheapest Price
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Questions & Answers

Map of how to get from Middletown to Chicago.ExpandLaunch map view
  • Distance: 765.1 mi
  • Duration: 5h 31m

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 48m.

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