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How to get fromOrange County to Chicagoby bus, plane, train (Amtrak), bus (Greyhound, Flixbus), car, taxi or bus (Greyhound)

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There are 10 ways to get from Orange County to Chicago by bus, plane, train (Amtrak), bus (Greyhound, Flixbus), car, taxi, 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 Matthew St Park and Ride - Goshen to Port Authority Bus Terminalbus bus
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 17m
    $107–516

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

    cheapest
    1. Take the bus from Matthew St Park and Ride - Goshen to Port Authority Bus Terminalbus bus
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 33m
    $82–316

  3. Train (Amtrak)

    1. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 1m
    $390–718

  4. Bus

    1. Take the bus from Matthew St Park and Ride - Goshen 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
    23h 1m
    $144–278

  5. Drive 778.9 mi

    1. Drive from Orange County to Chicagocar car 778.9 mi
    12h 53m
    $143–206

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

    1. Take the bus from Matthew St Park and Ride - Goshen 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
    6h 47m
    $94–318

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

    1. Take the bus from Matthew St Park and Ride - Goshen 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
    $459–630

  8. 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
    7h 35m
    $253–626

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

    1. Take the bus from Matthew St Park and Ride - Goshen 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 38m
    $134–393

  10. Bus via Baltimore

    1. Take the bus from Matthew St Park and Ride - Goshen 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
    24h 57m
    $192–398

Orange County to Chicago by bus

Calendar7Weekly Buses
Duration23h 1mAverage Duration
Ticket$144Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Poughkeepsie Amtrak Station to Chicago Union Station once daily. Tickets cost $250–550 and the journey takes 18h 2m. Alternatively, you can take a bus from Matthew St Park and Ride - Goshen to Chicago Bus Station via Port Authority Bus Terminal and Newark Penn Station in around 23h 1m.

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