Cheap flights from O'Hare Intl (ORD) to Westchester County
ORD — HPN
Nov 1 — Nov 81
Round-trip
1 adult, Economy
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Keep the following information in mind while searching for O'Hare Intl to Westchester County flight deals. Data was last updated October 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Popular in | September |
Cheapest in | January |
Average price | $266 |
Cheapflights Insights
Everything you need to know about your flight from Chicago O'Hare Intl Airport to Westchester County
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Westchester County?
Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Westchester County (average of $380). Flying from Chicago O'Hare Intl Airport to Westchester County in November is currently the most expensive (average of $523). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from ORD to REU?
Find hourly flight availability from O'Hare Intl to Westchester County. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 2, 2026.
When flying from Chicago O'Hare Intl Airport to Westchester County, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 8% versus a flight in the afternoon.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Westchester County?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Westchester County. Price data was last updated on September 26, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Westchester County flight should consider departing on Saturday afternoons when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Westchester County
Get insights into the airlines that provide service to Westchester County. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Westchester County. Reviews last updated October 2, 2026.
Read reviews from past customers who have flown American Airlines from Chicago O'Hare Intl Airport to Westchester County. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
7.9
Food
6.4
Overall
7.0
Comfort
7.2
Entertainment
6.8
Boarding
7.4
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Crew
7.9
Food
6.4
Overall
7.0
Comfort
7.2
Entertainment
6.8
Boarding
7.4
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Related info for your journey
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O'Hare Intl and Westchester County flights
Browse other O'Hare Intl and Westchester County flight options. Last updated on October 2, 2026.
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Top airline flying from O'Hare Intl to Westchester County
Discover the top airline that operate flights from O'Hare Intl to Westchester County. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$380 | Average$494 | FlexibilityNo cancel fee | On-time71% |