Chicago (ORD) to San Jose Cabo (SJD) flights
2 airlines fly nonstop from Chicago (ORD) to San Jose Cabo (SJD): American Airlines and United Airlines. The two airports are 1,807 miles (2,908 km) apart. American Airlines is in oneworld and United Airlines is in Star Alliance. There are also 39 ways to fly it with one stop, through Kansas City, Saint Louis and Dallas and more.
Airlines flying nonstop from ORD to SJD
- American Airlinesoneworld · bookable with 9 programsWho books it
- United AirlinesStar Alliance · bookable with 13 programsWho books it
Book ORD to SJD with points
Loyalty programs that can book at least one of the nonstop airlines, from the Award Booking Guide.
- Air Canada AeroplanBooks United Airlines
- Air New Zealand AirpointsBooks United Airlines
- Alaska Atmos RewardsBooks American Airlines
- American AAdvantageBooks American Airlines
- ANA Mileage ClubBooks United Airlines
- Avianca LifeMilesBooks United Airlines
- British Airways ClubBooks American Airlines
- Cathay Pacific Asia MilesBooks American Airlines
- Emirates SkywardsBooks United Airlines
- EVA Air Infinity MileageLandsBooks United Airlines
- Finnair PlusBooks American Airlines
- Iberia ClubBooks American Airlines
- JAL Mileage BankBooks American Airlines
- JetBlue TrueBlueBooks United Airlines
- Lufthansa Miles & MoreBooks United Airlines
- Qantas Frequent FlyerBooks American Airlines
- Qatar Airways Privilege ClubBooks American Airlines
- Singapore Airlines KrisFlyerBooks United Airlines
- TAP Miles&GoBooks United Airlines
- Thai Royal Orchid PlusBooks United Airlines
- Turkish Airlines Miles&SmilesBooks United Airlines
- United MileagePlusBooks United Airlines
ORD to SJD with one stop
39 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Kansas City (MCI)American Airlines and United Airlines, then Southwest Airlines
- Via Saint Louis (STL)American Airlines and United Airlines, then Southwest Airlines
- Via Dallas (DFW)American Airlines the whole way
- Via Austin (AUS)American Airlines the whole way
- Via Houston (IAH)United Airlines the whole way
- Via Monterrey (MTY)VivaAerobus the whole way
- Via Indianapolis (IND)American Airlines and United Airlines, then Southwest Airlines
- Via Nashville (BNA)American Airlines and United Airlines, then Southwest Airlines
- Via Denver (DEN)United Airlines the whole way
- Via Minneapolis (MSP)Delta Air Lines and Sun Country Airlines the whole way+1
- Via Phoenix (PHX)American Airlines the whole way
- Via Guadalajara (GDL)Volaris and VivaAerobus the whole way
- Via Leon/Guanajuato (BJX)Volaris the whole way
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Queretaro (QRO)Volaris and American Airlines, then VivaAerobus
ORD to SJD: common questions
Which airlines fly nonstop from ORD to SJD?
American Airlines (oneworld) and United Airlines (Star Alliance) fly nonstop from Chicago (ORD) to San Jose Cabo (SJD).
How far is Chicago from San Jose Cabo by plane?
Chicago (ORD) and San Jose Cabo (SJD) are 1,807 miles (2,908 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 SJD award flights?
22 programs can book at least one of the nonstop airlines: Air Canada Aeroplan, Air New Zealand Airpoints, Alaska Atmos Rewards, American AAdvantage, ANA Mileage Club, Avianca LifeMiles, British Airways Club, Cathay Pacific Asia Miles and 14 more. Which flights each can book depends on its partners, so check the airline before you transfer points.
How many miles does ORD to SJD 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 SJD with taxes and fees.
Where can I connect between Chicago and San Jose Cabo?
The most direct connections are through Kansas City (MCI), Saint Louis (STL), Dallas (DFW), Austin (AUS) and Houston (IAH). On 26 of them the same airline flies both flights, for example American Airlines through Dallas.
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.