Chicago (ORD) to San Jose (SJO) flights
One airline flies nonstop from Chicago (ORD) to San Jose (SJO): United Airlines. The two airports are 2,221 miles (3,574 km) apart. United Airlines is in Star Alliance. There are also 26 ways to fly it with one stop, through Nashville, Cancun and Atlanta and more.
Airlines flying nonstop from ORD to SJO
- United AirlinesStar Alliance · bookable with 13 programsWho books it
Book ORD to SJO 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
- ANA Mileage ClubBooks United Airlines
- Avianca LifeMilesBooks United Airlines
- Emirates SkywardsBooks United Airlines
- EVA Air Infinity MileageLandsBooks United Airlines
- JetBlue TrueBlueBooks United Airlines
- Lufthansa Miles & MoreBooks United 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 SJO with one stop
26 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Nashville (BNA)American Airlines and United Airlines, then Southwest Airlines
- Via Cancun (CUN)American Airlines, Frontier Airlines and 1 more, then Volaris Costa Rica and Volaris
Q6
- Via Atlanta (ATL)Delta Air Lines and Frontier Airlines the whole way
+1 - Via Tampa (TPA)American Airlines, Frontier Airlines and 1 more, then Breeze Airways
- Via Guanacaste (LIR)United Airlines and American Airlines, then SANSARZ
- Via Orlando (MCO)Frontier Airlines the whole wayQ6
- Via Miami (MIA)American Airlines the whole way
- Via Fort Lauderdale (FLL)JetBlue Airways the whole way
+1 - Via Charlotte (CLT)American Airlines the whole way
- Via Guatemala City (GUA)AVIANCA the whole way
- Via Houston (IAH)United Airlines the whole way
- Via Dallas (DFW)American Airlines and Frontier Airlines the whole way
- Via Austin (AUS)American Airlines and United Airlines, then Southwest Airlines
- Via Dulles (IAD)United Airlines the whole way
- Via Panama City (PTY)Copa Airlines the whole way
ORD to SJO: common questions
Which airlines fly nonstop from ORD to SJO?
United Airlines (Star Alliance) flies nonstop from Chicago (ORD) to San Jose (SJO).
How far is Chicago from San Jose by plane?
Chicago (ORD) and San Jose (SJO) are 2,221 miles (3,574 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 SJO award flights?
13 programs can book at least one of the nonstop airlines: Air Canada Aeroplan, Air New Zealand Airpoints, ANA Mileage Club, Avianca LifeMiles, Emirates Skywards, EVA Air Infinity MileageLands, JetBlue TrueBlue, Lufthansa Miles & More and 5 more. Which flights each can book depends on its partners, so check the airline before you transfer points.
How many miles does ORD to SJO 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 SJO with taxes and fees.
Where can I connect between Chicago and San Jose?
The most direct connections are through Nashville (BNA), Cancun (CUN), Atlanta (ATL), Tampa (TPA) and Guanacaste (LIR). On 18 of them the same airline flies both flights, for example Delta Air Lines through Atlanta.
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.