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How to get fromChicago to Middletownby plane, bus, bus (Flixbus, Greyhound), train, taxi, car, or bus (Greyhound)

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There are 12 ways to get from Chicago to Middletown by plane, bus, bus (Flixbus, Greyhound), train, taxi, car, or bus (Greyhound)

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 Midway International Airport to Laguardia Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the bus from Port Authority Bus Terminal to Railroad Ave - Middletown Terminalbus bus
    6h 52m
    $222–598

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the bus from White Plains Bus Center to Railroad Ave - Middletown Terminalbus bus
    8h 21m
    $112–532

  3. Bus

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus bus
    2. Take the bus from Newark Penn Station to Port Authority Bus Terminalbus bus 108
    3. Take the bus from Port Authority Bus Terminal to Railroad Ave - Middletown Terminalbus bus
    19h 41m
    $153–288

  4. Train, taxi

    1. Take the train from Chicago Union Station to Poughkeepsie Amtrak Stationtrain train Lake Shore Limited
    2. Take the taxi from Beacon to Middletowntaxi taxi
    19h 55m
    $422–772

  5. Drive 775.2 mi

    1. Drive from Chicago to Middletowncar car 775.2 mi
    12h 48m
    $142–205

  6. Fly Chicago O'Hare International Airport to Laguardia Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the bus from Port Authority Bus Terminal to Railroad Ave - Middletown Terminalbus bus
    7h 12m
    $152–698

  7. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the bus from Port Authority Bus Terminal to Railroad Ave - Middletown Terminalbus bus
    7h 24m
    $160–923

  8. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the bus from Port Authority Bus Terminal to Railroad Ave - Middletown Terminalbus bus
    7h 26m
    $344–914

  9. Fly Chicago O'Hare International Airport to Wilkes-Barre/Scranton International Airport, taxi, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Wilkes-Barre/Scranton International Airport (AVP)plane plane ORD - AVP
    2. Take the taxi from Wilkes-Barre/Scranton International Airport (AVP) to Sunoco Station, 54 Main Avetaxi taxi
    3. Take the bus from Sunoco Station, 54 Main Ave to Railroad Ave - Middletown Terminalbus bus
    7h 16m
    $252–638

  10. Fly Chicago Midway International Airport to Albany County Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    2. Take the bus from Albany to Newburghbus bus
    9h 17m
    $160–832

  11. Fly Chicago O'Hare International Airport to Lehigh Valley International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Lehigh Valley International Airport (ABE)plane plane ORD - ABE
    2. Take the bus from Lehigh Valley International Airport Trans Bridge Bus Stop to Port Authority Bus Terminalbus bus
    3. Take the bus from Port Authority Bus Terminal to Railroad Ave - Middletown Terminalbus bus
    9h 43m
    $150–480

  12. Bus 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 bus from Port Authority Bus Terminal to Railroad Ave - Middletown Terminalbus bus
    24h 10m
    $176–385

Chicago to Middletown by bus

Calendar16Weekly Buses
Duration19h 41mAverage Duration
Ticket$153Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Middletown.ExpandLaunch map view
  • Distance: 843.9 mi
  • Duration: 6h 52m

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

You can take a bus from Chicago Bus Station to Railroad Ave - Middletown Terminal via Newark Penn Station and Port Authority Bus Terminal in around 19h 41m.

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