Flights from Chicago to San Jose, Costa Rica

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
04/03/26
1 Stopover (MEX)
Y40703, Q64051
13h 05min
Return
04/16/26
1 Stopover (MEX)
Q64050, Y40700
14h 14min
Volaris, Volaris Costa Rica
$357
Best option
Chicago
San Jose, Costa Rica
Outbound
02/13/26
1 Stopover (PTY)
CM0236, CM0116
09h 52min
Return
02/26/26
direct
AA0346
05h 38min
Copa Airlines ?
$621
Chicago
San Jose, Costa Rica
Outbound
04/03/26
1 Stopover (MEX)
AM0689, AM0690
11h 08min
Return
04/16/26
1 Stopover (MEX)
AM0657, AM0682
14h 40min
Aeroméxico
$1,468
Chicago
San Jose, Costa Rica
Outbound
04/03/26
1 Stopover (MEX)
Y40703, Q64051
13h 05min
Return
04/16/26
1 Stopover (MEX)
Q64050, Y40700
14h 14min
Volaris, Volaris Costa Rica
$366
Chicago
San Jose, Costa Rica
Outbound
04/03/26
1 Stopover (MEX)
Y40703, Y44051
13h 05min
Return
04/16/26
1 Stopover (MEX)
Y44050, Y40700
14h 14min
Volaris ?
$427
Chicago
San Jose, Costa Rica
Outbound
02/13/26
1 Stopover (GDL)
Y41705, Q64059
10h 57min
Return
02/26/26
1 Stopover (MEX)
Q64050, Y40700
13h 53min
Volaris, Volaris Costa Rica ?
$476
Chicago
San Jose, Costa Rica
Outbound
02/13/26
1 Stopover (FLL)
NK0002, NK0335
07h 09min
Return
02/26/26
2 Stopovers (JFK, BOS)
B61794, B60118, B60311
20h 24min
Spirit Airlines ?
$489
Chicago
San Jose, Costa Rica
Outbound
02/13/26
1 Stopover (FLL)
NK0002, NK0335
07h 09min
Return
02/26/26
1 Stopover (FLL)
NK0338, NK3153
07h 41min
Spirit Airlines
$492
Chicago
San Jose, Costa Rica
Outbound
04/03/26
1 Stopover (PTY)
CM0229, CM0162
07h 39min
Return
04/16/26
1 Stopover (PTY)
CM0341, CM0235
14h 16min
Copa Airlines ?
$540
Chicago
San Jose, Costa Rica
Outbound
04/03/26
1 Stopover (IAH)
UA2665, UA2448
13h 56min
Return
04/16/26
1 Stopover (IAH)
UA1589, UA1752
10h 58min
United Airlines ?
$558
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 $356.92
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