Chicago (ORD) to Westchester County (HPN) flights
One airline flies nonstop from Chicago (ORD) to Westchester County (HPN): American Airlines. The two airports are 736 miles (1,185 km) apart. American Airlines is in oneworld. There are also 11 ways to fly it with one stop, through Detroit, Washington and Martha's Vineyard and more.
Airlines flying nonstop from ORD to HPN
- American Airlinesoneworld · bookable with 9 programsWho books it
Book ORD to HPN with points
Loyalty programs that can book at least one of the nonstop airlines, from the Award Booking Guide.
- Alaska Atmos RewardsBooks American Airlines
- American AAdvantageBooks American Airlines
- British Airways ClubBooks American Airlines
- Cathay Pacific Asia MilesBooks American Airlines
- Finnair PlusBooks American Airlines
- Iberia ClubBooks American Airlines
- JAL Mileage BankBooks American Airlines
- Qantas Frequent FlyerBooks American Airlines
- Qatar Airways Privilege ClubBooks American Airlines
ORD to HPN with one stop
11 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Washington (DCA)American Airlines the whole way
- Via Martha's Vineyard (MVY)American Airlines, then Cape Air and Tradewind Aviation
TJ - Via Raleigh/Durham (RDU)American Airlines and United Airlines, then Breeze Airways
- Via Nantucket (ACK)American Airlines and United Airlines, then Tradewind Aviation and JetBlue AirwaysTJ
- Via Charlotte (CLT)American Airlines the whole way
- Via Myrtle Beach (MYR)American Airlines and United Airlines, then Breeze Airways
- Via Minneapolis (MSP)Delta Air Lines the whole way+1
- Via Atlanta (ATL)Delta Air Lines the whole way+1
- Via Charleston (CHS)American Airlines and United Airlines, then Breeze Airways
- Via Savannah (SAV)American Airlines and United Airlines, then Breeze Airways
ORD to HPN: common questions
Which airlines fly nonstop from ORD to HPN?
American Airlines (oneworld) flies nonstop from Chicago (ORD) to Westchester County (HPN).
How far is Chicago from Westchester County by plane?
Chicago (ORD) and Westchester County (HPN) are 736 miles (1,185 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
Which points programs can book ORD to HPN award flights?
9 programs can book at least one of the nonstop airlines: Alaska Atmos Rewards, American AAdvantage, British Airways Club, Cathay Pacific Asia Miles, Finnair Plus, Iberia Club, JAL Mileage Bank, Qantas Frequent Flyer and 1 more. Which flights each can book depends on its partners, so check the airline before you transfer points.
How many miles does ORD to HPN cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for ORD to HPN with taxes and fees.
Where can I connect between Chicago and Westchester County?
The most direct connections are through Detroit (DTW), Washington (DCA), Martha's Vineyard (MVY), Raleigh/Durham (RDU) and Nantucket (ACK). On 5 of them the same airline flies both flights, for example Delta Air Lines through Detroit.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.