$28 Cheap flight deals from Chicago (CHI) to Sleepy Hollow (NYC)

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This Weekend's Flight Deals from Chicago to Sleepy Hollow

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Mar 15 - Sun, Apr 19
ORD
O'Hare Intl.
EWR
Newark Liberty Intl. Airport
$235 Roundtrip, found 1 hour ago
$235
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sun, Mar 15 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Sun, Apr 19, priced at $235 found 1 hour ago
Fri, Mar 13 - Tue, Mar 17
MDW
Midway Intl.
EWR
Newark Liberty Intl. Airport
$257 Roundtrip, found 11 hours ago
$257
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Fri, Mar 13 from Midway Intl. to Newark Liberty Intl. Airport, returning Tue, Mar 17, priced at $257 found 11 hours ago
Sat, Mar 14 - Tue, Mar 17
ORD
O'Hare Intl.
LGA
LaGuardia
$340 Roundtrip, just found
$340
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Mar 14 from O'Hare Intl. to LaGuardia, returning Tue, Mar 17, priced at $340 just found
Fri, Mar 13 - Sun, Mar 15
MDW
Midway Intl.
LGA
LaGuardia
$365 Roundtrip, found 5 hours ago
$365
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, Mar 13 from Midway Intl. to LaGuardia, returning Sun, Mar 15, priced at $365 found 5 hours ago

Airfares from $28 One Way, $57 Round Trip from Chicago to Sleepy Hollow

Prices starting at $57 for return flights and $28 for one-way flights to Sleepy Hollow were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Apr 22 - Wed, Apr 29
MDW
Chicago
EWR
New York
$57 Roundtrip, found 1 day ago
$57
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Chicago to New York, returning Wed, Apr 29, priced at $57 found 1 day ago
Tue, Apr 21 - Sat, Apr 25
ORD
Chicago
LGA
New York
$89 Roundtrip, found 1 hour ago
$89
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Apr 21 from Chicago to New York, returning Sat, Apr 25, priced at $89 found 1 hour ago
Tue, Mar 31 - Wed, Apr 8
ORD
Chicago
JFK
New York
$119 Roundtrip, found 12 hours ago
$119
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, Mar 31 from Chicago to New York, returning Wed, Apr 8, priced at $119 found 12 hours ago
Thu, Apr 30 - Sun, May 3
RFD
Rockford
LGA
New York
$143 Roundtrip, found 6 days ago
$143
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Apr 30 from Rockford to New York, returning Sun, May 3, priced at $143 found 6 days ago
Sat, May 30 - Mon, Jun 1
MDW
Chicago
LGA
New York
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 30 from Chicago to New York, returning Mon, Jun 1, priced at $160 found 2 days ago

Sleepy Hollow economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn White Plains/Tarrytown
3.0-star property

Hampton Inn White Plains/Tarrytown

8/10 Very Good! (1,376 reviews)

May 1 - May 4

3 night stay

Chicago (CHI) to White Plains (HPN)

Spirit Airlines • Roundtrip • Coach
Price was $432, price is now $310 per person
$310
per person
found 1 day ago
Room key didn’t work and towels were missing

Reviewed on Dec 28, 2025

Stamford Suites
4.0-star property

Stamford Suites

6.4/10 (101 reviews)

Apr 23 - Apr 26

3 night stay

Chicago (ORD) to White Plains (HPN)

Spirit Airlines • Roundtrip • Coach
Price was $500, price is now $384 per person
$384
per person
found 1 day ago
Many positives aspects to Stamford Suites. It was clean - especially the kitchen and, yes, there is a full kitchen with gas stove, full sized refrigerator (!) and even a small dishwasher. The suite was very roomy. Location in Stamford is great! The staff is very accommodating. I slept extremely well there-bed was quite comfortable. If you are staying for awhile and need storage there are multiple closets! Rooms are bright with natural light - important to me. Yes, the hotel is a bit tired around the edges. The shower faucet was not brilliant. No coffee maker in room. But the positives outweigh the minor inconveniences!

Reviewed on Oct 28, 2025

Cromwell Manor Inn
4.0-star property

Cromwell Manor Inn

9.4/10 Exceptional! (95 reviews)

Apr 29 - May 1

2 night stay

Chicago (CHI) to White Plains (HPN)

Frontier Airlines • Coach

White Plains (HPN) to Chicago (CHI)

Spirit Airlines • Coach
Price was $508, price is now $397 per person
$397
per person
found 1 day ago
The Cromwell was as beautiful and idyllic as the pictures promised, but was made even more spectacular by the warm and friendly staff who made our trip there so fun and homey. We can’t wait to come stay again!

Reviewed on Aug 15, 2025

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More About Flying To Sleepy Hollow from Chicago

Route Information for Flights from Chicago to Sleepy Hollow

Origin Airport IATA Code
CHI
Destination Airport IATA Code
NYC
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Sleepy Hollow

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.