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

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There are 9 ways to get from Chicago to Sleepy Hollow by subway, plane, train, train (Amtrak), bus (Flixbus), car, shuttle, bus, 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. 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 17m
    $194–577

  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 33m
    $108–511

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train Lake Shore Limited
    19h 47m
    $308–616

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    20h 38m
    $202–278

  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 38m
    $224–677

  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 26m
    $216–920

  9. 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 Port Authority Bus Terminalbus bus Washington
    23h 6m
    $182–386

Chicago to Sleepy Hollow by train (Amtrak)

Calendar7Weekly Trains
Duration19h 47mAverage Duration
Ticket$308Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Sleepy Hollow.ExpandLaunch map view
  • Distance: 761.4 mi
  • Duration: 5h 17m

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 $300–650 and the journey takes 19h 23m. Alternatively, Flixbus USA operates a bus from Chicago Bus Station to New York Midtown twice daily. Tickets cost $140–240 and the journey takes 17h 5m. Jefferson Lines also services this route once daily.

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