Flight Routes from Chicago to San Jose, Costa Rica

Trip type

Our cheapest offers for flights from Chicago to San Jose, Costa Rica

Here you can compare cheap flights from Chicago (CHI) to San Jose, Costa Rica (SJO) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to San Jose, Costa Rica. Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Chicago
San Jose, Costa Rica
Outbound
07/26/26
1 Stopover (MCO)
F93044, Y44001
23h 04min
Return
08/05/26
1 Stopover (MCO)
Y44000, F92791
15h 41min
Frontier Airlines, Volaris ?
$511
Best option
Chicago
San Jose, Costa Rica
Outbound
07/26/26
1 Stopover (FLL)
NK1986, NK0335
07h 12min
Return
08/05/26
1 Stopover (FLL)
NK0338, NK0001
10h 01min
Spirit Airlines
$544
Chicago
San Jose, Costa Rica
Outbound
07/26/26
1 Stopover (MEX)
AM0689, AM0690
11h 08min
Return
08/05/26
1 Stopover (MEX)
AM0691, AM0682
09h 28min
Aeroméxico
$1,246
Chicago
San Jose, Costa Rica
Outbound
07/26/26
1 Stopover (FLL)
NK1986, NK0335
07h 12min
Return
08/05/26
1 Stopover (FLL)
NK0338, NK0001
10h 01min
Spirit Airlines
$552
Chicago
San Jose, Costa Rica
Outbound
06/25/26
1 Stopover (GDL)
Y45703, Q64059
20h 56min
Return
06/30/26
1 Stopover (MEX)
Y44062, Y40700
21h 52min
Volaris, Volaris Costa Rica ?
$559
Chicago
San Jose, Costa Rica
Outbound
07/26/26
1 Stopover (GUA)
AV0631, AV0651
08h 35min
Return
08/05/26
1 Stopover (FLL)
NK0338, NK0001
10h 01min
Avianca ?
$594
Chicago
San Jose, Costa Rica
Outbound
06/25/26
1 Stopover (MIA)
AA2690, AA1593
18h 50min
Return
06/30/26
1 Stopover (MIA)
AA1788, AA0581
17h 02min
American Airlines
$597
Chicago
San Jose, Costa Rica
Outbound
06/25/26
1 Stopover (MIA)
AA1380, AA1353
14h 16min
Return
06/30/26
1 Stopover (MIA)
AA1788, AA0581
17h 02min
American Airlines ?
$598
Chicago
San Jose, Costa Rica
Outbound
07/26/26
1 Stopover (IAH)
UA2665, UA2448
13h 50min
Return
08/05/26
1 Stopover (IAH)
UA1097, UA1617
09h 31min
United Airlines ?
$605
Chicago
San Jose, Costa Rica
Outbound
07/26/26
1 Stopover (IAH)
UA1231, UA1280
13h 07min
Return
08/05/26
1 Stopover (IAH)
UA1097, UA1617
09h 31min
United Airlines ?
$606
Prices based on recent searches, subject to last-minute changes
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Tips and tricks to help you find cheap flights from Chicago to San Jose, Costa Rica

Favorite airline: Copa
Flight tickets on the route Chicago – San Jose, Costa Rica are most frequently booked with Copa.
Copa
26 %
Spirit Airlines
23 %
United Airlines
19 %
Direct flights are more expensive
On this route, direct flights are $173.00 more expensive than flights with a stopover.
non stop flight
1 stop
2 stops
06h 45min
25h 29min
15h 50min
$452
$279
$352
Favourite connection: via Panama City
35 % of booked tickets on this route are for flights with a transfer in Panama City.
Route
bookings
1 stopover Panama City-Tocumen International
30h 15min, from $412
35 %
1 stopover Houston - George Bush Intercontinental Airport, TX
13h 56min, from $311
23 %
1 stopover Mexico City-Juarez International
17h 13min, from $634
12 %

Important flight information

Flight information: Chicago - San Jose, Costa Rica

Roundtrip from $510.13
Flight duration min. 05:12
Return flight duration min. 05:37
Distance 3566 km
Flights per week 8
Departure airport Airport Chicago-IL, all airports (CHI)
Arrival airport Airport San Jose, Costa Rica (SJO)
Destination country Flights to Costa Rica
Alternative flights to San Jose, Costa Rica
Flight destinations with a similar price
Flight destinations with a similar price