Rome2Rio

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

Find Transport to Middletown

See all options

There are 11 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 32m
    $76–337

  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 27m
    $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 52m
    $103–260

  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 57m
    $124–486

  5. Drive 790.4 mi

    1. Drive from Chicago to Middletowncar car 790.4 mi
    13h 24m
    $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 6m
    $82–430

  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 25m
    $818–1,043

  8. 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 51m
    $100–1,101

  9. 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 41m
    $104–495

  10. Bus, train via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the train from New York Penn Station to Middletown Njtrain train
    23h 33m
    $113–293

  11. 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 35m
    $136–543

Chicago to Middletown by bus and train

Calendar7Weekly Services
Duration20h 52mAverage Duration
Ticket$103Cheapest Price
See schedules

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 57m.

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

Trips from Chicago

Trips to Middletown

Popular routes