Chicago (ORD) to San Juan (SJU) flights
3 airlines fly nonstop from Chicago (ORD) to San Juan (SJU): American Airlines, Frontier Airlines and United Airlines. The two airports are 2,074 miles (3,338 km) apart. American Airlines is in oneworld and United Airlines is in Star Alliance. There are also 42 ways to fly it with one stop, through Charlotte, Raleigh/Durham and Indianapolis and more.
Airlines flying nonstop from ORD to SJU
- American Airlinesoneworld · bookable with 9 programsWho books it
- Frontier AirlinesNot in an allianceWho books it
- United AirlinesStar Alliance · bookable with 13 programsWho books it
Book ORD to SJU 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 SJU with one stop
42 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Charlotte (CLT)American Airlines the whole way
- Via Raleigh/Durham (RDU)American Airlines and United Airlines, then Frontier Airlines, JetBlue Airways and 1 more
- Via Indianapolis (IND)American Airlines and United Airlines, then Southwest Airlines
- Via Columbus (CMH)American Airlines and United Airlines, then Southwest Airlines
- Via Richmond (RIC)American Airlines and United Airlines, then JetBlue Airways
- Via Norfolk (ORF)American Airlines and United Airlines, then JetBlue Airways
- Via Punta Cana (PUJ)Arajet the whole way
- Via Jacksonville (JAX)American Airlines and United Airlines, then Frontier Airlines and JetBlue Airways
- Via Atlanta (ATL)Delta Air Lines and Frontier Airlines the whole way+1
- Via Cleveland (CLE)American Airlines and United Airlines, then Frontier Airlines
- Via Dulles (IAD)United Airlines the whole way
- Via Nashville (BNA)American Airlines and United Airlines, then Southwest Airlines
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Washington (DCA)American Airlines and United Airlines, then JetBlue Airways
- Via Saint Thomas (STT)United Airlines and American Airlines, then Cape Air, JetBlue Airways and 1 more
ORD to SJU: common questions
Which airlines fly nonstop from ORD to SJU?
American Airlines (oneworld), Frontier Airlines and United Airlines (Star Alliance) fly nonstop from Chicago (ORD) to San Juan (SJU).
How far is Chicago from San Juan by plane?
Chicago (ORD) and San Juan (SJU) are 2,074 miles (3,338 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 SJU 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 SJU 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 SJU with taxes and fees.
Where can I connect between Chicago and San Juan?
The most direct connections are through Charlotte (CLT), Raleigh/Durham (RDU), Indianapolis (IND), Columbus (CMH) and Richmond (RIC). On 23 of them the same airline flies both flights, for example American Airlines through Charlotte.
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.