How much is a flight from Chicago to Westchester?

There’s no fixed price — fares between Chicago and Westchester County can vary a lot by day or time.

Pick a travel date to see today’s available fares.

Flying during the week can be more affordable, as weekend flights tend to be pricier. Also consider demand and availability: the last remaining seats often come at higher fares!

Which departure and arrival airports are available?

Between Chicago and Westchester County, flight options may depend on the combination of airports available.

• Airports in Chicago: Chicago is connected by 3 airports - Midway, O'Hare, Rockford.
• Airports in Westchester County: Westchester County is the only active airport in the area.

Sometimes flying into a nearby city can be more cost-effective. When a city has multiple airports, it’s worth comparing different flight combinations.

Choose the right flight for your trip from Chicago to Westchester

Jetcost helps you tailor your flight search based on what matters to you — flight length, budget, airline, or agency. Whether you prefer round-trip or one-way, direct or with stopovers, you’ll see options from eDreams, Expedia, and more.

Other popular destinations

Flying to United States? Many users also explore: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Looking for a specific airline? Select it directly in the filters to speed up your search. The search filters help you see only the options that match your needs.