There are most likely no direct flights on the Chicago — Westchester County route
Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Chicago to Westchester County. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Chicago to Westchester County
A non-stop flight is the most convenient and comfortable way to fly from Chicago to Westchester County, despite the fact that sometimes flights with transfers can cost significantly less.
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There are most likely no direct flights on the Chicago — Westchester County route
Chicago — Westchester County
11/04/2026
Departure
Direct flight
AA3499
starting at $208
Chicago — Westchester County
11/02/2026
Departure
Direct flight
AA5501
starting at $504
starting at $208
starting at $240
Flights from Chicago to Westchester County are operated by several airlines — American Airlines and Allegiant Air. This allows passengers to flexibly choose flights based on departure time, cost, and additional services. The minimum ticket price starts at $208, making this destination accessible to travelers with different budgets. We help compare all available options in real time, so you can book tickets at the best value for money. The service ensures transparent search and lets you book affordable flights in just a few clicks.
The cheapest flight ticket from Chicago to Westchester County according to data for the last 48 hours costs $208
Often the best time to buy tickets from Chicago to Westchester County is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Chicago to Westchester County can be found flying in these months: October.
The fastest flights from Chicago to Westchester County start from 2 hours 15 minutes in the air.
The following airlines operate direct flights on the route Chicago — Westchester County: American Airlines
We couldn't find any special offers for flights from Chicago to Westchester County
The cheapest one-way flight from Chicago to Westchester County departs on 11/03/2026, is operated by American Airlines and costs $208
There is no information about the cheapest roundtrip flight from Chicago to Westchester County
Fastest flight from Chicago to Westchester County takes 2h 15m
There are direct flights on this route 2 days a week: Mo and We
The distance between Chicago and Westchester County is 1158km (718 miles). There are 40 direct flights from Chicago to Westchester County. The time difference between Chicago and Westchester County is 1h. Flights from Chicago begin at 8:14 AM. The latest flight from Chicago departs at 7:30 PM
