Chicago to Westchester County flights
Routavio compares airline fares from several flight booking sites. The lowest one-way fare it found for Chicago to Westchester County is €186 (checked on 29 Oct 2026).
Your next trip, last seen at €151
Frontier Airlines · 3 stops · One wayWhen to fly
Explore datesMore dates worth a look
Find the dates that work for you
The lowest fare we observed for each month. Open a month to see its days, then pick your outbound and return. A day with no price is one we will search for you.
One-way fare
- Lowest observed
- €186, departing 3 Nov 2026 (Last checked: 29 Oct 2026)One-way fareCheck live prices for this route
- Non-stop, one way
- €186, departing 3 Nov 2026 (Last checked: 29 Oct 2026)
- Airlines seen
- Allegiant Air, Breeze Airways, Frontier Airlines, JetBlue
- Non-stop
- Yes
About this route
Explore the fares we observed from Chicago to Westchester County. Prices move often, so pick your dates to see the latest options.
- Route distance
- 1,158 km
- Seen on fares with a connection
- Frontier Airlines, Breeze Airways, Allegiant Air, JetBlue
- Alternative airports
- CGX, DPA, MDW, PWK, RFD
Route-level information; individual journeys vary.
A clearer picture of your fare
If the observed fare for this date drops, we will email you. At most one message a day.
Airport to city: straight-line distance
- Chicago Midway International Airport (MDW) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 14 km.
- Chicago O'Hare International Airport (ORD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 25 km.
- Chicago Rockford International Airport (RFD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 126 km.
- Westchester County Airport (HPN) → Westchester County, city gazetteer reference point (41.0340, -73.7629): ≈ 6 km.
Approximate distances calculated from coordinates, not road distances or travel times. These airports serve the city; they are not confirmed endpoints of an offer.
Frequently asked
How much is a flight from Chicago to Westchester County?
The lowest fare Routavio has observed is €186, found on 29 Oct 2026. Prices move, so read it as a floor rather than a quote.
When is the cheapest month to fly from Chicago to Westchester County?
In our observations November 2026 is the cheapest month so far, at €186.
Which airlines fly from Chicago to Westchester County?
Routavio has seen these carriers on the route: Allegiant Air, Breeze Airways, Frontier Airlines, JetBlue.
How long does the flight from Chicago to Westchester County take?
Across the 70 fares Routavio observed, the average journey time is 23h 09m, including any stops. Individual departures vary; the fastest observed flight is listed in the route facts above.
How many of the observed Chicago to Westchester County fares were non-stop?
1 of the 73 fares we observed were non-stop; the rest included at least one stop. That describes our observations, not every flight that operates.
How much is a non-stop flight from Chicago to Westchester County?
Cheapest non-stop one-way fare: €186, departing 3 Nov 2026 (checked 29 Oct 2026).
How observed prices work, what "No data" means and what a fare includes: Read the flight price guide · Price and schedule freshness on Routavio
Keep exploring
Similar routes
More routes from Chicago
Show all 36 routes →Show fewer ↑
More routes to Westchester County
Show all 30 routes →Show fewer ↑
Recently observed fares. Prices may change.