American AirlinesDepart17:50
Sat, Nov 14HPN → ORD
2h 59m · Direct
$152one way, per person
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- Cheapest fare
- $152
- Cheapest month
- November
- Direct flights
- Yes
- Flight time
- 2h 54m
American Airlines · Sat, Nov 14
from $152
American Airlines
1,160 km
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Cheapest month to fly from Westchester County to Chicago
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.
See every date in November 2026 →Plan the rest of your trip to Chicago
Where to stay, what to do and getting around, from our travel partners.
About flights from Westchester County to Chicago
Westchester County (HPN) and Chicago (CHI) are about 1,160 km apart. Direct flights take around 2h 54m, and recent direct fares were with American Airlines. Over the next few months, one-way fares start from $152, 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 Westchester County to Chicago?
The cheapest one-way fare we've seen recently is $152 with American Airlines, departing Saturday, November 14, 2026.
What is the cheapest month to fly from Westchester County to Chicago?
November 2026 currently has the lowest fares, from $152 one way.
Are there direct flights from Westchester County to Chicago?
Yes. Recent direct fares were with American Airlines.
How long is the flight from Westchester County to Chicago?
A direct flight takes about 2h 54m. Westchester County and Chicago are around 1,160 km apart.
Which airlines fly from Westchester County to Chicago?
Recent fares on this route were with American Airlines.
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