Westchester County (HPN) to Chicago (ORD) flights
One airline flies nonstop from Westchester County (HPN) to Chicago (ORD): 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 HPN to ORD
- American Airlinesoneworld · bookable with 9 programsWho books it
Book HPN to ORD 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
HPN to ORD 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)Cape Air and Tradewind Aviation, then American Airlines
TJ - Via Raleigh/Durham (RDU)Breeze Airways, then American Airlines and United Airlines
- Via Nantucket (ACK)Tradewind Aviation and JetBlue Airways, then American AirlinesTJ
- Via Charlotte (CLT)American Airlines the whole way
- Via Myrtle Beach (MYR)Breeze Airways, then American Airlines and United Airlines
- Via Minneapolis (MSP)Delta Air Lines the whole way+1
- Via Atlanta (ATL)Delta Air Lines the whole way+1
- Via Charleston (CHS)Breeze Airways, then American Airlines and United Airlines
- Via Savannah (SAV)Breeze Airways, then American Airlines and United Airlines
HPN to ORD: common questions
Which airlines fly nonstop from HPN to ORD?
American Airlines (oneworld) flies nonstop from Westchester County (HPN) to Chicago (ORD).
How far is Westchester County from Chicago by plane?
Westchester County (HPN) and Chicago (ORD) 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 HPN to ORD 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 HPN to ORD cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for HPN to ORD with taxes and fees.
Where can I connect between Westchester County and Chicago?
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.