Rome2Rio

How to get fromArmonk to Chicagoby plane, train (Amtrak), bus (Flixbus), car, bus, train or bus (Greyhound)

Find Transport to Chicago

See all options

There are 9 ways to get from Armonk to Chicago by plane, train (Amtrak), bus (Flixbus), car, bus, 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 Westchester County Airport to Chicago O'Hare International Airport

    best
    1. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)planeHPN - ORD
    4h 39m
    $475–908

  2. Line 0012 bus, train, bus to Laguardia Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Bedford Rd @ North Castle Townhall to White Plains Bus Terminal Lane Bbus
    2. Take the train from White Plains to 125th Street - Harlemtrain
    3. Take the bus from E 125 St/Lexington Av to Laguardia Rd/94 Stbus
    4. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)planeLGA - ORD
    6h 36m
    $70–289

  3. Train (Amtrak)

    1. Take the train from Croton-Harmon Amtrak Station to Chicago Union StationtrainLake Shore Limited
    19h 9m
    $159–387

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus StationbusFlixBus N2640
    24h 13m
    $108–218

  5. Drive 814.9 mi

    1. Drive from Armonk to Chicagocar814.9 mi
    13h 29m
    $149–215

  6. Line 0012 bus, train, bus to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the bus from Bedford Rd @ North Castle Townhall to White Plains Bus Terminal Lane Bbus
    2. Take the train from White Plains to 125th Street - Harlemtrain
    3. Take the bus from E 125 St/Lexington Av to Laguardia Rd/94 Stbus
    4. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)planeLGA - MDW
    6h 25m
    $90–439

  7. Line 0012 bus, train, bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Bedford Rd @ North Castle Townhall to White Plains Bus Terminal Lane Bbus
    2. Take the train from White Plains to Grand Central Terminaltrain
    3. Take the bus from Bryant Park to Terminal Bbus
    4. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)planeEWR - ORD
    7h 17m

  8. Line 0012 bus, train, train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Bedford Rd @ North Castle Townhall to White Plains Bus Terminal Lane Bbus
    2. Take the train from White Plains to Grand Central Terminaltrain
    3. Take the train from Grand Central Terminal to Jamaicatrain
    4. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)planeJFK - ORD
    7h 8m
    $777–1,141

  9. Bus via Baltimore

    1. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus StationbusGreyhound US0670 / ...
    2. Take the bus from Baltimore Downtown Bus Station to Chicago Bus StationbusGreyhound US0164
    25h 37m
    $129–290

Armonk to Chicago by bus (Flixbus)

Calendar10Weekly Buses
Duration24h 13mAverage Duration
Ticket$108Cheapest Price
See schedules

Questions & Answers

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

American Airlines and Delta fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD) every 3 hours. Alternatively, Amtrak operates a train from Croton-Harmon Amtrak Station to Chicago Union Station once daily. Tickets cost $120–340 and the journey takes 18h 46m.

Transport is disrupted due to the Russia-Ukraine war. Read more

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

More Questions & Answers

Where to next?

Trips from Armonk

Trips to Chicago

Popular routes