RareNonstop · 5h
CHI to SJUPuerto Rico
San Juan
$162
usually $340
−52%
Most monthly lows $287–$340. Cheaper than every other month on record (3).
Flights · CHI → SJO
Chicago to San José
Best fare, round trip
$291
Too little price history on this route to compare — the fare is shown as found.
Found
- Depart
- Thu 24 Dec
- Return
- Mon 4 Jan
- Stay
- 11 nights
- Flight
- 1 stop · 7h
- Airline
Copa Airlines
Cached fare — the booking search re-prices live before you pay.
Costa RicaSan JoséNobody comes for the capital — they come for two coasts, volcanoes and cloud forest, all within four hours.Best windowDec–AprAirportsJuan Santamaría (SJO)Every route into San JoséFare seasonality
When this route gets cheap.
The cheapest itinerary we are tracking makes one stop and takes about 7 hours outbound, on a 11-night trip — ticketed under Copa Airlines, which on a connecting fare need not operate every leg. At $291 for 3,569 km each way, that works out to about $41 per 1,000 km flown. That is about the $43 per 1,000 km typical of medium-haul fares here. Across the 7 departure cities we track at a similar distance from San José, this fare ranks 2nd — 17% above the $249 from New York. That puts it in the cheaper half of the 8 routes of similar length we watch out of Chicago, where the middle fare is $373. We have 1 month of cached prices for this route so far — not enough to call a fare cheap or expensive, so we publish the price without a percentage. Fare history here is still too short to name a cheap season. The best time to be in San José: Dec–Apr.
The 2 days we hold a cached fare for
Press a date to compare its fares
The median cached fare across this calendar is 9% higher than when tracking began on 8 Aug — $394 then versus $429 now, across 14 recorded snapshots. This is a calendar-level trend, so an individual deal above can be lower. The lowest single day we have seen here is $291, on 24 Dec.
These are the only days we have a cached price for on this route so far — not the only days it flies. The search above covers any date.
Cached fares · checked 15 Oct 2026
We are still collecting this route's months — 1 month of cached prices so far, too few to chart.
Route facts
- Airports
- O’Hare (ORD) · Midway (MDW) ↔ Juan Santamaría (SJO)
- Flight time
- ≈7 hours outbound
- Distance
- ≈3,569 km each way
- Airlines on the board
- Copa Airlines
- Itineraries
- Connections on current fares
- Best months to visit
- Dec–Apr
Good to know
CHI → SJO, answered.
How far in advance should I book CHI → San José?
We do not publish a number for this, because we cannot measure it yet. Answering it honestly means watching the same departure date on this route over many weeks as it approaches, and that archive is still filling up — so any "book N days ahead" figure here would be borrowed from somewhere else rather than measured. Our guide Why flight prices change covers the levers we can measure.
Are there nonstop flights from Chicago to San José?
The current cheapest fares involve a connection, ticketed under Copa Airlines. We hold no nonstop fare on this route right now, which does not mean none flies — search your exact dates to see what does.
Are these prices guaranteed?
No — these are cached fares found on real searches (this one on 17 October). Airlines reprice constantly, so the booking search re-checks the live price before you pay. Fresher finds are far more likely to still be available.
Next step
Sleeping in San José?
Lock the flight first — then compare stays for 24 Dec – 4 Jan '27 · 11 nights.
Browse hotelsMissed it?
Cached fares expire. This route has a feed of its own — follow it and the next CHI → SJO drop reaches you as soon as we find it.
Follow this route’s feedKeep browsing
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