Cheap flights from Chicago to Westchester County
✈️ Fares in November 2026 start from €184 — found by real travellers in the last 48 hours.
Compare all Chicago → Westchester County flights
Cheapest day to fly in November 2026
| Date | From | Stops | |
|---|---|---|---|
| Fri 13 Nov | €184 | 2 stops | Book → |
Popular flights from Chicago
Flights to Westchester County from other cities
Frequently asked questions
How much is a flight from Chicago to Westchester County?
Cached market fares for November 2026 start from €184 one-way. Prices are found by real travellers in the last 48 hours and confirmed at checkout.
Which airlines fly from Chicago to Westchester County?
Recent fares on this route are offered by F9 and others. ScanFlyGo compares 1,200+ airlines and agencies.
What is the cheapest day to fly from Chicago to Westchester County?
ScanFlyGo shows the cheapest fare for each day of November 2026 — check the price table above to pick the cheapest date, then book directly with the provider.
Is Chicago to Westchester County a direct flight?
Both direct and connecting options may be available. Use the ScanFlyGo search to filter by stops, airline and time.
Can I track my Chicago to Westchester County flight live?
Yes. ScanFlyGo has a built-in live flight tracker with a real-time map, so you can follow your aircraft on the day by flight number.
Does ScanFlyGo charge booking or service fees?
No. ScanFlyGo is a free flight metasearch — we compare fares and send you to the airline or agency to book. The price is confirmed at their checkout with no extra fee from us.
About Chicago to Westchester County flights
ScanFlyGo compares Chicago (O'Hare International Airport, ORD) to Westchester County (Westchester County Airport, HPN) fares across 1,200+ airlines and agencies via the Aviasales network. The cheapest fare found for November 2026 is €184. Prices shown are the lowest cached market fares; the final price is always confirmed at the partner's checkout. You can also search the return route Westchester County → Chicago, or use the full live search for exact dates, stops, airline filters and a live map to track your flight on the day.
Plan the rest of your trip to Westchester County
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