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Chicago to Sleepy Hollow buses

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Trip Overview

The average bus between Chicago and Sleepy Hollow takes 36h 3m and the fastest bus takes 34h 17m. The bus 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.

36h 3m
Duration
1,024 mi
Distance
$241
Average price
6 times a week
Frequency

Chicago to Sleepy Hollow bus times

Buses run 6 times a week between Chicago and Sleepy Hollow. The earliest departure is at 12:25 PM in the afternoon, and the last departure from Chicago is at 7:15 PM which arrives into Sleepy Hollow at 6:32 AM. All services require a transfer at Baltimore and take an average of 36h 3m. The schedules shown below are for the next available departures.

Departing Sunday, November 1, 2026

  •  → 

    Arrives +2 days

    Flixbus USAFlixbus USAWestchester County Bee-Line System34h 17m • 2 changes

Departing Monday, November 2, 2026

  •  → 

    Arrives +2 days

    Flixbus USAFlixbus USAWestchester County Bee-Line System34h 17m • 2 changes

Departing Tuesday, November 3, 2026

  •  → 

    Arrives +2 days

    Flixbus USAFlixbus USAWestchester County Bee-Line System41h 7m • 2 changes

Departing Wednesday, November 4, 2026

  •  → 

    Arrives +2 days

    Flixbus USAFlixbus USAWestchester County Bee-Line System34h 17m • 2 changes

Departing Thursday, November 5, 2026

  •  → 

    Arrives +2 days

    Flixbus USAFlixbus USAWestchester County Bee-Line System35h 34m • 2 changes

Departing Friday, November 6, 2026

  •  → 

    Arrives +2 days

    Flixbus USAFlixbus USAWestchester County Bee-Line System36h 51m • 2 changes

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: 1,023.7 mi
  • Duration: 36h 3m

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

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.

Operators