Rome2Rio

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

Find Transport to Chicago

See all options

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 29m
    $76–336

  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 28m
    $58–306

  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 44m
    $93–216

  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 53m
    $150–438

  5. Drive 789.7 mi

    1. Drive from Middletown to Chicagocar car 789.7 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 train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 22m
    $88–476

  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 train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 39m
    $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 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 8m
    $101–1,081

  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 train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    8h 50m
    $85–394

  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
    23h 34m
    $86–226

  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 2m
    $163–566

Middletown to Chicago by train and bus

Calendar7Weekly Services
Duration21h 44mAverage Duration
Ticket$93Cheapest Price
See schedules

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.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

More Questions & Answers

Where to next?

Trips from Middletown

Trips to Chicago

Popular routes