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Chicago to Sleepy Hollow trains

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Trip Overview

The average train between Chicago and Sleepy Hollow takes 19h 44m and the fastest train takes 19h 43m. The train runs, on average, 6 times per week from Chicago to Sleepy Hollow. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

19h 44m
Duration
932 mi
Distance
$608
Average price
6 times a week
Frequency

Chicago to Sleepy Hollow train times

Trains run 6 times a week between Chicago and Sleepy Hollow. The service departs Chicago at 9:30 PM at night, which arrives into Sleepy Hollow at 18:13:00. All services require a transfer, and take on average 19h 44m. The schedules shown below are for the next available departures.

Departing Wednesday, November 11, 2026

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    Arrives next day

    AmtrakMetro-North Railroad (MNR)19h 43m • 1 change

Departing Thursday, November 12, 2026

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    Arrives next day

    AmtrakMetro-North Railroad (MNR)19h 43m • 1 change

Departing Friday, November 13, 2026

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    Arrives next day

    AmtrakMetro-North Railroad (MNR)19h 48m • 1 change

Departing Saturday, November 14, 2026

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    Arrives next day

    AmtrakMetro-North Railroad (MNR)19h 48m • 1 change

Departing Sunday, November 15, 2026

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    Arrives next day

    AmtrakMetro-North Railroad (MNR)19h 43m • 1 change

Departing Monday, November 16, 2026

  •  → 

    Arrives next day

    AmtrakMetro-North Railroad (MNR)19h 43m • 1 change

Frequently asked questions

Want to know about travelling from Chicago to Sleepy Hollow? We have put together a list of the most frequently asked questions from our users such as: What is the cheapest mode of transport? What is the quickest option? How much do tickets usually cost? and many more.

Map of how to get from Chicago to Sleepy Hollow.ExpandLaunch map view
  • Distance: 932 mi
  • Duration: 19h 44m

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.

Operators