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How to get fromMiddletown to Chicagoby bus, plane, bus (Greyhound, Flixbus), taxi, train, car, or bus (Greyhound)

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There are 10 ways to get from Middletown to Chicago by bus, plane, bus (Greyhound, Flixbus), taxi, train, 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. Bus to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Railroad Ave - Middletown Terminal to Port Authority Bus Terminalbus bus
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 21m
    $219–587

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

    cheapest
    1. Take the bus from Railroad Ave - Middletown Terminal to Main St & Broadwaybus bus
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 42m
    $112–582

  3. Bus

    1. Take the bus from Railroad Ave - Middletown Terminal to Port Authority Bus Terminalbus bus
    2. Take the bus from Port Authority Bus Terminal to Newark Penn Stationbus bus 108
    3. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus
    19h 57m
    $141–279

  4. Taxi, train (Amtrak)

    1. Take the taxi from Middletown to Beacontaxi taxi
    2. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h
    $427–791

  5. Drive 774 mi

    1. Drive from Middletown to Chicagocar car 774 mi
    12h 46m
    $142–204

  6. Bus to Laguardia Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Railroad Ave - Middletown Terminal to Port Authority Bus Terminalbus bus
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 41m
    $149–687

  7. Bus, taxi to Wilkes-Barre/Scranton International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Railroad Ave - Middletown Terminal to Sunoco Station, 54 Main Avebus bus
    2. Take the taxi from Sunoco Station, 54 Main Ave to Wilkes-Barre/Scranton International Airport (AVP)taxi taxi
    3. Fly from Wilkes-Barre/Scranton International Airport (AVP) to Chicago O'Hare International Airport (ORD)plane plane AVP - ORD
    6h 16m
    $258–647

  8. Bus, bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Railroad Ave - Middletown Terminal to Port Authority Bus Terminalbus bus
    2. Take the bus from Port Authority Bus Terminal to Terminal Bbus bus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    7h 3m
    $161–909

  9. Bus, bus to Lehigh Valley International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Railroad Ave - Middletown Terminal to Port Authority Bus Terminalbus bus
    2. Take the bus from Port Authority Bus Terminal to Lehigh Valley International Airport Trans Bridge Bus Stopbus bus
    3. Fly from Lehigh Valley International Airport (ABE) to Chicago O'Hare International Airport (ORD)plane plane ABE - ORD
    9h 55m
    $136–434

  10. Bus via Baltimore

    1. Take the bus from Railroad Ave - Middletown Terminal to Port Authority Bus Terminalbus bus
    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 14m
    $169–379

Middletown to Chicago by bus

Calendar15Weekly Buses
Duration19h 57mAverage Duration
Ticket$141Cheapest Price
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Questions & Answers

Map of how to get from Middletown to Chicago.ExpandLaunch map view
  • Distance: 818.5 mi
  • Duration: 6h 21m

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

You can take a bus from Railroad Ave - Middletown Terminal to Chicago Bus Station via Port Authority Bus Terminal and Newark Penn Station in around 19h 57m.

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