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
08/20/26
1 Stopover (PTY)
CM0236, CM0787
24h 08min
Return
08/25/26
1 Stopover (PTY)
CM0839, CM0235
29h 45min
Copa Airlines ?
$509
found 3 days ago
Best option
Chicago
San Jose, Costa Rica
Outbound
08/20/26
1 Stopover (FLL)
B60664, B60039
06h 57min
Return
08/25/26
1 Stopover (FLL)
B60038, B60863
08h 42min
JetBlue Airways
$567
found 3 days ago
Chicago
San Jose, Costa Rica
Outbound
06/25/26
1 Stopover (MEX)
AM0689, AM0690
11h 08min
Return
06/30/26
1 Stopover (MEX)
AM0657, AM0682
14h 40min
Aeroméxico
$1,489
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
06/25/26
1 Stopover (FLL)
NK2209, NK0335
16h 45min
Return
06/30/26
1 Stopover (MEX)
Q64062, Y40700
21h 52min
Spirit Airlines
$591
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
08/20/26
1 Stopover (PTY)
CM0236, CM0391
11h 57min
Return
08/25/26
1 Stopover (PTY)
CM0839, CM0228
18h 42min
Copa Airlines
$623
found 3 days ago
Chicago
San Jose, Costa Rica
Outbound
08/20/26
2 Stopovers (YTZ, YUL)
AC8550, AC7954, AC1847
31h 20min
Return
08/25/26
1 Stopover (GDL)
Q64058, Y41704
18h 54min
Air Canada
$641
found 3 days ago
Chicago
San Jose, Costa Rica
Outbound
08/20/26
2 Stopovers (YTZ, YUL)
AC8550, AC7954, AC1847
31h 20min
Return
08/25/26
1 Stopover (GDL)
Q64058, Y41704
18h 54min
Air Canada
$653
found 3 days ago
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 508,80 $
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
Departure airport - Destination country Chicago-IL, all airports - Costa Rica
Alternative flights to San Jose, Costa Rica
Flight destinations with a similar price
Flight destinations with a similar price