$69 Cheap flight deals from Chicago (CHI) to Sleepy Hollow (NYC)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
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.
Airfares from $69 One Way, $150 Round Trip from Chicago to Sleepy Hollow
Prices starting at $150 for return flights and $69 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.
Sleepy Hollow economy flight packages
Delamar Southport
Jul 20 - Jul 22
Chicago (ORD) to White Plains (HPN)
White Plains (HPN) to Chicago (ORD)
Reviewed on Jan 17, 2026
Luxury 3BR Family Home Game Room Parking
Jul 17 - Jul 19
Chicago (ORD) to White Plains (HPN)
White Plains (HPN) to Chicago (ORD)
Hotel Nyack, a JdV by Hyatt Hotel
Jul 9 - Jul 13
Chicago (CHI) to White Plains (HPN)
Reviewed on Jun 5, 2026
Sleepy Hollow packages with premium economy flights
Tarrytown House Estate
Jul 24 - Jul 26
Chicago (CHI) to White Plains (HPN)
Reviewed on May 29, 2026
Hotel NoMa, Trademark Collection by Wyndham
Jul 24 - Jul 26
Chicago (CHI) to White Plains (HPN)
Reviewed on Nov 30, 2025
Royal Regency Hotel
Jul 24 - Jul 26
Chicago (CHI) to White Plains (HPN)
Reviewed on Mar 22, 2026
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
Find bargain tickets for flights from Chicago to Sleepy Hollow, and plan your whole trip in just minutes with Orbitz. With Orbitz’s guaranteed low fares, there is no need to wait for special sales to find deals.
Cheap Flights From Chicago to Sleepy Hollow Through Orbitz
You need a vacation but you have a tight budget, and searching for discount Chicago to Sleepy Hollow flights has become an exercise in frustration. It's time to stop combing through never-ending search engine results, and go straight to Orbitz.
Guaranteed Low Fares for Chicago to Sleepy Hollow Flights
Whether you are looking for domestic or international flights, Orbitz offers you the lowest price. With our low price guarantee on flights from Chicago to Sleepy Hollow, you know you are getting the best deal out there.
Frequent Flyer Miles and Points on Your Flights From Chicago to Sleepy Hollow
Not only will you pay a low fare through Orbitz, but you can also get credit for frequent flyer miles or points. All you have to do is add your frequent flyer number in the appropriate field when you book Chicago to Sleepy Hollow flights that qualify.
Arrange Flights From Chicago to Sleepy Hollow Cutting-Edge Mobile Tools
We know you are busy, so with our mobile apps for Android and iOS devices, you can search for flights, book your seats, and make cancellations while standing in line or in a waiting room. You can also find great discounts on hotel rooms and vacation packages that go with your Chicago to Sleepy Hollow flights.
Flights from Chicago
- Chicago to Orlando
- Chicago to Houston
- Chicago to New York
- Chicago to Dallas
- Chicago to Phoenix
- Chicago to Los Angeles
- Chicago to New Orleans
- Chicago to London
- Chicago to Washington
- Chicago to Paris
- Chicago to Toronto
- Chicago to Rome
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Sacramento
- Chicago to Kansas City
- Chicago to Hartford
- Chicago to Atlantic City
Sleepy Hollow Airports
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.