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

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There are 9 ways to get from Middletown Ny to Chicago by train, plane, bus (Flixbus), train (Amtrak), car, or bus

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 Ny to Secaucus Lower Leveltrain train
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 28m
    $184–906

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

    cheapest
    1. Take the train from Middletown Ny to Sufferntrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    9h
    $101–484

  3. Bus

    1. Take the bus from Middletown to New Yorkbus bus
    2. Take the bus from New York to Newarkbus bus
    3. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus
    21h 1m
    $217–351

  4. Train (Amtrak)

    1. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    21h 41m
    $293–630

  5. Drive 777.1 mi

    1. Drive from Middletown Ny to Chicagocar car 777.1 mi
    12h 49m
    $142–205

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

    1. Take the train from Middletown Ny to Secaucus Lower Leveltrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 10m
    $195–607

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

    1. Take the train from Middletown Ny to Secaucus Lower Leveltrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    7h 31m
    $225–707

  8. Train, bus

    1. Take the train from Middletown Ny to Hobokentrain train
    2. Take the bus from Hoboken Terminal to Port Authority Bus Terminalbus bus 126
    3. Take the bus from Port Authority Bus Terminal to Baltimorebus bus
    4. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    25h 57m
    $204–353

  9. Train via Newark

    1. Take the train from Middletown Ny to Secaucus Lower Leveltrain train Mnbnp
    2. Take the train from Newark Penn Station to Chicago Union Stationtrain train Cardinal
    31h 12m
    $365–785

Middletown Ny to Chicago by foot, bus, and train (Amtrak)

Calendar7Weekly Services
Duration21h 41mAverage Duration
Ticket$293Cheapest Price
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Questions & Answers

Map of how to get from Middletown Ny to Chicago.ExpandLaunch map view
  • Distance: 810.9 mi
  • Duration: 6h 28m

What companies run services between Middletown Ny, NY, USA and Chicago, IL, USA?

You can take a vehicle from Middletown Ny to Chicago Bus Station via Middletown, New York, and Newark Penn Station in around 21h 1m. Alternatively, Amtrak operates a train from Poughkeepsie Amtrak Station to Chicago Union Station once daily. Tickets cost $280–600 and the journey takes 18h 2m.

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