Cheap flights from Chicago O'Hare to San Juan Puerto Rico
Chicago O'Hare to San Juan Puerto Rico (ORD → SJU). We are tracking 5 fares on this route.
Cheapest tracked fare $113 · typical price $264 · you save about $151 (57%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
American Airlines
2026-09-19
1 stop
$113
—
2026-11-10
Direct
$116
Frontier Airlines
2026-11-02
1 stop
$138
Frontier Airlines
2027-01-01
Direct
$207
United Airlines
2027-01-09
1 stop
$219
Could you save more?
The airport you were going to fly from is often not the cheapest one. Compare every airport in a region against each other, or check whether a multi-day stopover beats the direct fare.
How cheap can flights from Chicago O'Hare to San Juan Puerto Rico get?
The cheapest fare we have tracked on this route is $113, compared with a typical $264 for a trip of this distance.
Is it cheaper to fly to San Juan Puerto Rico from a different airport?
Often, yes. Fares out of secondary airports are frequently cheaper than the obvious hub, but they are the ones most likely to be missing from a normal search. Our reverse search compares every airport in a region against each other so the cheaper departure point is not hidden.
Could a stopover make Chicago O'Hare to San Juan Puerto Rico cheaper?
Sometimes. On thin long-haul routes a two-leg trip with a multi-day stopover can beat the direct fare, and occasionally a direct fare is not sold at all. Our detour search prices those routings against the direct flight.