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How to get fromChicago to Sleepy Hollowby subway, plane, train, train (Amtrak), bus (Greyhound), car, shuttle, bus, or bus (Flixbus)

Find Transport to Sleepy Hollow

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There are 10 ways to get from Chicago to Sleepy Hollow by subway, plane, train, train (Amtrak), bus (Greyhound), car, shuttle, bus, or bus (Flixbus)

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Subway to Chicago Midway International Airport, fly to Laguardia Airport, train

    best
    1. Take the subway from Adams/Wabash to Midwaysubway subway
    2. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    3. Take the train from 125th Street - Harlem to Tarrytowntrain train
    5h 23m
    $214–677

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, line 13 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 Terminal Lane F to Wildey St @ Valley Stbus bus
    6h 39m
    $88–441

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train Lake Shore Limited
    19h 49m
    $517–796

  4. Bus via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus Greyhound US0164
    2. Take the bus from Baltimore to New Yorkbus bus Ppb 8724 / ...
    23h 41m
    $181–300

  5. Drive  804.7 mi

    1. Drive from Chicago to Sleepy Hollowcar car 804.7 mi
    13h 29m
    $147–213

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to Tarrytowntrain train
    5h 40m
    $144–577

  7. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the train from Jamaica to Grand Central Terminaltrain train
    3. Take the train from Grand Central Terminal to Tarrytowntrain train
    5h 51m
    $336–888

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take a shuttle bus from Newark Airport Terminal B to Grand Centralshuttle bus
    6h 27m
    $176–920

  9. Fly Chicago Midway International Airport to Philadelphia International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL)plane plane MDW - PHL
    2. Take the train from 30th Street Station to Ny Moynihan Train Hall At Penn Stationtrain train
    7h 13m
    $176–997

  10. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640 / ...
    23h 45m
    $154–230

Chicago to Sleepy Hollow by train (Amtrak)

Calendar7Weekly Trains
Duration19h 49mAverage Duration
Ticket$517Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Sleepy Hollow.ExpandLaunch map view
  • Distance: 761.4 mi
  • Duration: 5h 23m

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

Amtrak operates a train from Chicago Union Station to Croton-Harmon Amtrak Station once daily. Tickets cost $500–800 and the journey takes 19h 23m. Alternatively, you can take a bus from Chicago Bus Station to Tarrytown via Baltimore, New York, West 42nd Street & 8th Avenue, E 42 St/Madison Av, and Grand Central Terminal in around 23h 41m.

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