Rome2Rio

How to get fromChicago to Orange Countyby plane, bus, train (Amtrak), bus (Flixbus, Greyhound), car, train or bus (Greyhound)

Find Transport to Orange County

See all options

There are 10 ways to get from Chicago to Orange County by plane, bus, train (Amtrak), bus (Flixbus, Greyhound), car, train, 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 Main St & Grand St - Goshenbus bus
    6h 56m
    $102–478

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

    cheapest
    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 Main St & Grand St - Goshenbus bus
    7h 18m
    $78–298

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Poughkeepsie Amtrak Stationtrain train Lake Shore Limited
    20h 1m
    $252–492

  4. 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 Main St & Grand St - Goshenbus bus
    22h 47m
    $129–316

  5. Drive 779.7 mi

    1. Drive from Chicago to Orange Countycar car 779.7 mi
    12h 53m
    $143–206

  6. 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 Main St & Grand St - Goshenbus bus
    7h 27m
    $838–1,064

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

    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 Matthew St Park and Ride - Goshenbus bus
    8h
    $98–470

  8. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Frank R Lautenberg Secaucus Lower Level to Harrimantrain train
    7h 54m
    $78–361

  9. 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 Main St & Grand St - Goshenbus bus
    9h 50m
    $150–450

  10. 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 Matthew St Park and Ride - Goshenbus bus
    24h 3m
    $130–281

Chicago to Orange County by bus

Calendar7Weekly Buses
Duration22h 47mAverage Duration
Ticket$129Cheapest Price
See schedules

Questions & Answers

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

Amtrak operates a train from Chicago Union Station to Poughkeepsie Amtrak Station once daily. Tickets cost $130–340 and the journey takes 18h 43m. Alternatively, you can take a bus from Chicago Bus Station to Main St & Grand St - Goshen via Newark Penn Station and Port Authority Bus Terminal in around 22h 47m.

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

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers

Trips from Chicago

Trips to Orange County

Popular routes