American AirlinesDepart18:37
Sat, Nov 14ORD → HPN
2h 22m · Direct
$162one way, per person
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- Cheapest fare
- $162
- Cheapest month
- November
- Direct flights
- Yes
- Flight time
- 2h 14m
American Airlines · Sat, Nov 14
from $162
American Airlines
1,160 km
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Cheapest month to fly from Chicago to Westchester County
Lowest one-way fare per person in each month. Choose a month to see every date.
Cheapest dates in November 2026
The lowest fares we've seen for each day, cheapest first.
American Airlines
Allegiant AirDepart09:30
Thu, Nov 12RFD → HPN
7h 03m · 2 stops
$184one way, per person
View deal
American AirlinesDepart14:02
Tue, Nov 10ORD → HPN
2h 14m · Direct
$199one way, per person
View deal
Allegiant AirDepart13:08
Sun, Nov 8RFD → HPN
6h 59m · 3 stops
$314one way, per person
View deal
Plan the rest of your trip to Westchester County
Where to stay, what to do and getting around, from our travel partners.
About flights from Chicago to Westchester County
Chicago (CHI) and Westchester County (HPN) are about 1,160 km apart. Direct flights take around 2h 14m, and recent direct fares were with American Airlines. Over the next few months, one-way fares start from $162, and November 2026 is currently the cheapest month to fly.
These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.
Frequently asked questions
How much is a flight from Chicago to Westchester County?
The cheapest one-way fare we've seen recently is $162 with American Airlines, departing Saturday, November 14, 2026.
What is the cheapest month to fly from Chicago to Westchester County?
November 2026 currently has the lowest fares, from $162 one way.
Are there direct flights from Chicago to Westchester County?
Yes. Recent direct fares were with American Airlines.
How long is the flight from Chicago to Westchester County?
A direct flight takes about 2h 14m. Chicago and Westchester County are around 1,160 km apart.
Which airlines fly from Chicago to Westchester County?
Recent fares on this route were with American Airlines and Allegiant Air.
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