Travel within United States is: Fully open. See details.

There are 11 ways to get from Chicago to Sleepy Hollow by plane, subway, train, bus or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2rio's travel planner.

Recommended option

Fly Chicago O'Hare to New York La Guardia, line 7 subway, train  •  5h 44m

  1. Fly from Chicago O'Hare (ORD) to New York La Guardia (LGA) ORD - LGA
  2. Take the line 7 subway from Woodside-61 St to Grand Central-42 St
  3. Take the train from Grand Central to Tarrytown

Cheapest option

Bus  •  14h 41m

  1. Take the bus from Chicago to New York, NY - 3 Allen St Chicago

$55 - $103

9 alternative options

Fly Chicago Midway to New York La Guardia, train  •  5h 34m

  1. Fly from Chicago Midway (MDW) to New York La Guardia (LGA) MDW - LGA
  2. Take the train from Grand Central to Tarrytown

Fly Chicago O'Hare to Newark, train  •  5h 58m

  1. Fly from Chicago O'Hare (ORD) to Newark (EWR) ORD - EWR
  2. Take the train from Grand Central to Tarrytown

Fly Chicago O'Hare to New York JFK, subway, train  •  6h 8m

  1. Fly from Chicago O'Hare (ORD) to New York JFK (JFK) ORD - JFK
  2. Take the subway from Sutphin Blvd-Archer Av-JFK Airport to 5 Av/53 St
  3. Take the train from Grand Central to Tarrytown

Fly Chicago O'Hare to White Plains, line 13 bus  •  6h 22m

  1. Fly from Chicago O'Hare (ORD) to White Plains (HPN) ORD - HPN
  2. Take the line 13 bus from Martin Luther King Blvd @ Main St to Wildey St @ Valley St

$104 - $341

Fly Chicago Midway to Philadelphia, train  •  7h 10m

  1. Fly from Chicago Midway (MDW) to Philadelphia (PHL) MDW - PHL
  2. Take the train from Philadelphia to New York Moynihan Train Hall
  3. Take the train from Grand Central to Tarrytown

Fly Chicago O'Hare to Allentown/Bethlehem/Easton, bus  •  8h

  1. Fly from Chicago O'Hare (ORD) to Allentown/Bethlehem/Easton (ABE) ORD - ABE
  2. Take the bus from Lehigh Valley International Airport Trans Bridge Bus Stop to Franklin & Varick

$156 - $428

Bus via Broadway @ W 262Nd St  •  16h 16m

  1. Take the bus from Chicago, IL to New York

$100 - $123

Train  •  19h 32m

  1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Station Lake Shore Limited

$95 - $140

Drive  •  13h 22m

  1. Drive from Chicago to Sleepy Hollow 811.6 miles

$75 - $120

Chicago to Sleepy Hollow by trains

The train journey time between Chicago and Sleepy Hollow is around 19h 31m and covers a distance of around 938 miles. The fastest train normally takes 19h 31m. Operated by Amtrak and MTA Bus Company, the Chicago to Sleepy Hollow train service departs from Chicago Union Station and arrives in Tarrytown. Typically six trains run weekly, although weekend and holiday schedules can vary so check in advance.

Train route overview

Average train time:
19h 31m
Fastest train time:
19h 31m
Trains per week:
6
Cheapest price:
-
Carbon emissions:
79 kg CO2

First and last trains

First train departs at:
21:30
Last train departs at:
21:30

The schedules shown below are for the next available departures.

Chicago to Sleepy Hollow train schedules

Chicago → Sleepy Hollow
Fully open

Travel safe during COVID-19

Rules to follow in United States

2m

Recommended

Travel within United States

Domestic border crossings may be subject to approval, testing and quarantine
Nationwide control measures in place

COVID-19 help in United States

If you need help, visit the national COVID-19 website or call the COVID-19 Helpline 800-232-4636

Frequently Asked Questions


Yes, travel within United States is currently allowed.

Explore travel options

Domestic travel is not restricted, but some conditions may apply

  • Face masks are recommended
  • There is a social distancing requirement of 2 metres
  • Domestic border crossings may be subject to approval, testing and quarantine
  • Nationwide control measures in place

Explore travel options

The national COVID-19 helpline number in Sleepy Hollow is 800-232-4636.

Wearing a face mask on public transport in Sleepy Hollow is recommended.

The social distance requirement in Sleepy Hollow is 2 metres.

Make yourself known to an official member of staff and/or call the national coronavirus helpline number on 800-232-4636.

Last updated: 8 Jun 2021
Exceptions may apply, for full details: Centers for Disease control and prevention (CDC).

We're working around the clock to bring you the latest COVID-19 travel updates.
This information is compiled from official sources. To the best of our knowledge, it is correct as of the last update.
Visit Rome2rio travel advice for general help.

Questions & Answers

The cheapest way to get from Chicago to Sleepy Hollow is to drive which costs $75 - $120 and takes 13h 22m.

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The fastest way to get from Chicago to Sleepy Hollow is to fly and line 13 bus which takes 6h 22m and costs $100 - $350.

More details

No, there is no direct train from Chicago station to Sleepy Hollow. However, there are services departing from Chicago Union Station and arriving at Tarrytown via Croton-Harmon. The journey, including transfers, takes approximately 19h 32m.

More details

The distance between Chicago and Sleepy Hollow is 718 miles. The road distance is 811.6 miles.

Get driving directions

The best way to get from Chicago to Sleepy Hollow without a car is to bus which takes 14h 41m and costs $50 - $110.

More details

It takes approximately 5h 44m to get from Chicago to Sleepy Hollow, including transfers.

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Chicago to Sleepy Hollow train services, operated by Amtrak, depart from Chicago Union Station.

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The best way to get from Chicago to Sleepy Hollow is to bus which takes 14h 41m and costs $50 - $110. Alternatively, you can train, which costs $95 - $140 and takes 19h 32m.

Mode details

The quickest flight from Chicago O'Hare Airport to New York La Guardia Airport is the direct flight which takes 2h 3m.

Search flights

Sleepy Hollow is 1h ahead of Chicago. It is currently 5:53 AM in Chicago and 6:53 AM in Sleepy Hollow.

Map of how to get from Chicago to Sleepy Hollow.
Launch map view
  • Distance: 718.2 miles
  • Duration: 5h 44m

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

Wanda Coach operates a bus from Chicago to New York, NY - 3 Allen St 3 times a week. Tickets cost $50 - $100 and the journey takes 13h. Alternatively, Amtrak operates a train from Chicago Union Station to Croton-Harmon Amtrak Station once daily. Tickets cost $95 - $140 and the journey takes 19h 5m.

Airlines
United Airlines
Website
united.com
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2h 10m
When
Every day
Estimated price
$75 - $550
Flights from Chicago O'Hare to Newark
Ave. Duration
2h 29m
When
Every day
Estimated price
$85 - $360
Flights from Chicago O'Hare to Newark via Pittsburgh
Ave. Duration
3h 59m
When
Every day
Estimated price
$85 - $360
Flights from Chicago O'Hare to Newark via Detroit
Ave. Duration
3h 59m
When
Monday to Saturday
Estimated price
$85 - $360
Flights from Chicago O'Hare to Newark via Milwaukee
Ave. Duration
4h 5m
When
Every day
Estimated price
$85 - $360
Flights from Chicago O'Hare to Newark via Cleveland
Ave. Duration
4h 6m
When
Every day
Estimated price
$85 - $360
Flights from Chicago O'Hare to White Plains
Ave. Duration
2h 12m
When
Every day
Estimated price
$140 - $600
Flights from Chicago O'Hare to Allentown/Bethlehem/Easton
Ave. Duration
1h 59m
When
Every day
Estimated price
$150 - $650
Flights from Chicago O'Hare to Allentown/Bethlehem/Easton via Washington Dulles
Ave. Duration
4h 38m
When
Every day
Estimated price
$150 - $650
American Airlines
Website
aa.com
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2h 9m
When
Every day
Estimated price
$75 - $340
Flights from Chicago O'Hare to Newark
Ave. Duration
2h 12m
When
Every day
Estimated price
$90 - $440
Flights from Chicago O'Hare to New York JFK
Ave. Duration
2h 26m
When
Every day
Estimated price
$100 - $600
Flights from Chicago O'Hare to New York JFK via Cleveland
Ave. Duration
3h 53m
When
Tuesday, Thursday, Saturday and Sunday
Estimated price
$100 - $600
Flights from Chicago O'Hare to New York JFK via Reagan Washington
Ave. Duration
4h 25m
When
Every day
Estimated price
$100 - $600
Flights from Chicago O'Hare to New York JFK via Covington
Ave. Duration
4h 20m
When
Every day
Estimated price
$100 - $600
Flights from Chicago O'Hare to New York JFK via Baltimore
Ave. Duration
5h
When
Every day
Estimated price
$100 - $600
Flights from Chicago O'Hare to White Plains
Ave. Duration
2h 17m
When
Every day
Estimated price
$95 - $480
Flights from Chicago O'Hare to White Plains via Reagan Washington
Ave. Duration
5h 10m
When
Every day
Estimated price
$95 - $480
Flights from Chicago O'Hare to White Plains via Charlotte
Ave. Duration
4h 54m
When
Every day
Estimated price
$95 - $480
Flights from Chicago O'Hare to Allentown/Bethlehem/Easton
Ave. Duration
2h 1m
When
Every day
Estimated price
$270 - $650
Flights from Chicago O'Hare to Allentown/Bethlehem/Easton via Charlotte
Ave. Duration
4h 46m
When
Every day
Estimated price
$270 - $650
Delta
Website
delta.com
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2h 15m
When
Every day
Estimated price
$70 - $340
Flights from Chicago Midway to New York La Guardia via Detroit
Ave. Duration
4h 12m
When
Every day
Estimated price
$75 - $380
Flights from Chicago O'Hare to New York JFK
Ave. Duration
2h 21m
When
Every day
Estimated price
$70 - $340
Flights from Chicago O'Hare to New York JFK via Detroit
Ave. Duration
4h 36m
When
Every day
Estimated price
$70 - $340
Flights from Chicago O'Hare to New York JFK via Boston
Ave. Duration
4h 47m
When
Every day
Estimated price
$95 - $340
Flights from Chicago O'Hare to New York JFK via Raleigh/Durham
Ave. Duration
4h 55m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$100 - $340
Flights from Chicago O'Hare to White Plains via Detroit
Ave. Duration
4h 40m
When
Every day
Estimated price
$90 - $450
Flights from Chicago O'Hare to White Plains via Atlanta
Ave. Duration
5h 11m
When
Every day
Estimated price
$170 - $450
Flights from Chicago Midway to Philadelphia via Detroit
Ave. Duration
4h 32m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$80 - $410
Flights from Chicago O'Hare to Allentown/Bethlehem/Easton via Detroit
Ave. Duration
4h 22m
When
Monday to Saturday
Estimated price
$65 - $360
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to New York La Guardia
Ave. Duration
2h 8m
When
Every day
Estimated price
$90 - $300
Flights from Chicago Midway to New York La Guardia via Baltimore
Ave. Duration
4h 1m
When
Every day
Estimated price
$90 - $300
Flights from Chicago Midway to Philadelphia
Ave. Duration
1h 53m
When
Every day
Estimated price
$100 - $360
Flights from Chicago Midway to Philadelphia via Nashville
Ave. Duration
4h 40m
When
Saturday
Estimated price
$110 - $400
JetBlue Airways
Website
jetblue.com
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2h 9m
When
Every day
Estimated price
$75 - $340
Flights from Chicago O'Hare to Newark
Ave. Duration
2h 11m
When
Every day
Estimated price
$90 - $440
Flights from Chicago O'Hare to New York JFK
Ave. Duration
2h 27m
When
Every day
Estimated price
$100 - $550
Spirit Airlines
Website
spirit.com
Flights from Chicago O'Hare to New York La Guardia
Ave. Duration
2h 7m
When
Every day
Estimated price
$55 - $350
Train operators
MTA

The New York City Subway consists of 27 underground lines that serve Manhattan, the Bronx, Brooklyn and Queens. Lines are identified by a number or letter as well as a colour. Subway passes (called MetroCards) are available for purchase from ticket machines and desks in subway stations (choose from Pay-Per-Ride or 7/30-Day Unlimited), and a new contactless payment system called OMNY is currently being rolled out. The subway runs 24 hours a day, 365 days a year.

Contact Details
Website
mta.info
Subway from Woodside-61 St to Grand Central-42 St
Ave. Duration
17 min
Frequency
Every 5 minutes
Estimated price
$3
Website
mta.info
Subway from Sutphin Blvd-Archer Av-JFK Airport to 5 Av/53 St
Ave. Duration
28 min
Frequency
Every 10 minutes
Estimated price
$3
Website
mta.info
MTA Bus Company
Website
mta.info
Train from Grand Central to Tarrytown
Ave. Duration
55 min
Frequency
Every 30 minutes
Schedules at
mta.info
Amtrak

Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.

Rome2rio's guide to Amtrak
Contact Details
Phone
+1 215-856-7924
Website
amtrak.com
Train from Philadelphia to New York Moynihan Train Hall
Ave. Duration
1h 13m
Frequency
Hourly
Estimated price
$27 - $40
Schedules at
amtrak.com
Coach Seat
$27 - $40
Premium
$180 - $260
Flexi Coach Seat
$40 - $65
Business Seat
$40 - $60
Train from Chicago Union Station to Croton-Harmon Amtrak Station
Ave. Duration
19h 5m
Frequency
Once daily
Estimated price
$95 - $140
Schedules at
amtrak.com
Coach Seat
$95 - $140
Premium
$310 - $440
Flexi Coach Seat
$190 - $280
Business Seat
$200 - $290
Amtrak Northeast Regional

Amtrak’s Northeast Regional train service serves the US’ busy northeast corridor from Virginia to Massachusetts; major stops include Boston, Providence, New York City, Philadelphia, Washington DC and Baltimore. Amenities include Wi-Fi, a quiet car, cafe and business-class seating, and travelling with a small dog or cat is permitted. Book at least 14 days in advance for a cheaper Saver Fare.

Rome2rio's guide to Amtrak Northeast Regional
Contact Details
Phone
+1 215-856-7924
Website
amtrak.com
Train from Philadelphia to New York Moynihan Train Hall
Ave. Duration
1h 28m
Frequency
Hourly
Estimated price
$40 - $85
Schedules at
amtrak.com
Reserved Coach Seat
$40 - $85
Business Class Seat
$65 - $130
Bus operators
Westchester County Bee-Line System
Phone
+1 914 995-2000
Website
transportation.westchestergov.com
Bus from Martin Luther King Blvd @ Main St to Wildey St @ Valley St
Ave. Duration
31 min
Frequency
Hourly
Estimated price
$3
Schedules at
transportation.westchestergov.com
All other routes
$3
BxM4C/Rte28 Westchester-Manhattan Express
$8
Trans-bridge Lines
Phone
+1 610-868-6001
Email
webmaster@transbridgelines.com
Website
transbridgelines.com
Bus from Lehigh Valley International Airport Trans Bridge Bus Stop to Franklin & Varick
Ave. Duration
1h 50m
Frequency
Twice daily
Estimated price
$30 - $50
Schedules at
transbridgelines.com
Wanda Coach
Phone
646-630-7186
Email
help@wandacoach.com
Website
wandacoach.com
Bus from Chicago to New York, NY - 3 Allen St
Ave. Duration
13h
Frequency
3 times a week
Estimated price
$50 - $100
Book at
GoTo Bus
D&W Bus
Website
gotobus.com
Bus from Chicago, IL to New York
Ave. Duration
12h 15m
Frequency
3 times a week
Estimated price
$90 - $110
Schedules at
gotobus.com
Book at
gotobus.com

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More Questions & Answers

Chicago to Sleepy Hollow train services, operated by Amtrak, arrive at Croton-Harmon Amtrak Station.

More details

Yes, the driving distance between Chicago to Sleepy Hollow is 812 miles. It takes approximately 13h 22m to drive from Chicago to Sleepy Hollow.

Get driving directions

Spirit Airlines, American Airlines, United Airlines and Delta offer flights from Chicago O'Hare Airport to New York La Guardia Airport.

Search flights

There are 83+ hotels available in Sleepy Hollow. Prices start at $100 USD per night.

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The best way to get from Chicago to Chicago O'Hare Airport is to subway which takes 42 min and costs $2 - $5.

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