$145 Cheap flight deals from Chicago (CHI) to Peekskill (NYC)

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This Weekend's Flight Deals from Chicago to Peekskill

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.

Sat, Jul 12 - Sat, Jul 19
ORD
O'Hare Intl.
HPN
Westchester County
$450 Roundtrip, found 4 days ago
$450
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Jul 12 from O'Hare Intl. to Westchester County, returning Sat, Jul 19, priced at $450 found 4 days ago

Airfares from $145 One Way, $297 Round Trip from Chicago to Peekskill

Prices starting at $297 for return flights and $145 for one-way flights to Peekskill were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Oct 14 - Mon, Nov 3
ORD
Chicago
HPN
White Plains
$297 Roundtrip, found 1 day ago
$297
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 14 from Chicago to White Plains, returning Mon, Nov 3, priced at $297 found 1 day ago
Tue, Oct 14 - Wed, Oct 29
ORD
Chicago
HPN
White Plains
$300 Roundtrip, found 1 day ago
$300
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 14 from Chicago to White Plains, returning Wed, Oct 29, priced at $300 found 1 day ago
Tue, Aug 12 - Tue, Aug 26
ORD
Chicago
HPN
White Plains
$302 Roundtrip, found 1 day ago
$302
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 12 from Chicago to White Plains, returning Tue, Aug 26, priced at $302 found 1 day ago
Mon, Oct 13 - Wed, Oct 29
ORD
Chicago
HPN
White Plains
$303 Roundtrip, found 1 day ago
$303
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Oct 13 from Chicago to White Plains, returning Wed, Oct 29, priced at $303 found 1 day ago
Thu, Aug 14 - Tue, Aug 26
ORD
Chicago
HPN
White Plains
$305 Roundtrip, found 1 day ago
$305
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Aug 14 from Chicago to White Plains, returning Tue, Aug 26, priced at $305 found 1 day ago

Peekskill 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

7.8/10 Good! (1,041 reviews)

Aug 15 - Aug 18

3 night stay

Chicago (CHI) to White Plains (HPN)

JetBlue Airways • Roundtrip • Coach
per person
found 15 hours ago
Nice hotel. Conveniently located. Nothing fancy but affordable.

Reviewed on May 14, 2025

Tarrytown House Estate on the Hudson
3.5-star property

Tarrytown House Estate on the Hudson

8/10 Very Good! (1,002 reviews)

Aug 24 - Aug 26

2 night stay

Chicago (ORD) to White Plains (HPN)

American Airlines • Roundtrip • Coach
per person
just found
While the front desk staff were very accommodating and the room itself was very spacious there were some areas that were lacking, especially for the price. The room revealed many maintenance issues that should have been addressed, most of which were not small items. The hotel contains many buildings with levels in each. These were not elevator accessible and only staircase. This made navigating with suitcases a chore. Older people or those with disabilities will find this extremely challenging.

Reviewed on Nov 1, 2024

Hyatt Regency Greenwich
4.0-star property

Hyatt Regency Greenwich

8.2/10 Very Good! (951 reviews)

Aug 16 - Aug 19

3 night stay

Chicago (CHI) to White Plains (HPN)

Spirit Airlines • Coach

White Plains (HPN) to Chicago (CHI)

United • Coach
per person
found 1 day ago
This is our 8th or 9th stay with you as we have family in Old Greenwich. The renovations are welcomed and it's nice to have dining once again at the hotel. There is not enough staff at the restaurant/bar area though. We had to add our drinks at the reception desk because no one came to bring us our check on the evening of 6/27/25. Also the back entrance from the parking area needs to be kept swept and clean.

Reviewed on Jul 1, 2025

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Peekskill first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hilltop Inn & Suites
2.5-star property

Hilltop Inn & Suites

7/10 Good! (241 reviews)

Aug 15 - Aug 18

3 night stay

Chicago (ORD) to White Plains (HPN)

Delta • Roundtrip • FirstClass
per person
found 1 day ago
Hyatt Regency Greenwich
4.0-star property

Hyatt Regency Greenwich

8.2/10 Very Good! (951 reviews)

Aug 15 - Aug 18

3 night stay

Chicago (ORD) to White Plains (HPN)

Delta • Roundtrip • FirstClass
per person
found 1 day ago
This is our 8th or 9th stay with you as we have family in Old Greenwich. The renovations are welcomed and it's nice to have dining once again at the hotel. There is not enough staff at the restaurant/bar area though. We had to add our drinks at the reception desk because no one came to bring us our check on the evening of 6/27/25. Also the back entrance from the parking area needs to be kept swept and clean.

Reviewed on Jul 1, 2025

Stamford Suites
4.0-star property

Stamford Suites

5.6/10 (39 reviews)

Aug 15 - Aug 18

3 night stay

Chicago (ORD) to White Plains (HPN)

Delta • Roundtrip • FirstClass
per person
found 1 day ago
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More About Flying To Peekskill from Chicago

Route Information for Flights from Chicago to Peekskill

Origin Airport IATA Code
CHI
Destination Airport IATA Code
NYC
Distance
736 mi
Direct Flight Airlines
American Airlines, Qatar Airways, Alaska Airlines
Earliest Flight Arrival
3:29PM UTC
Latest Flight Arrival
2:59AM UTC

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Orbitz looks for the best deals on Chicago to Peekskill flights for you. Mix and match airlines for your departing and return flights to fit your travel schedule and budget.

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.