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
09/19/25
2 Stopovers (IAH, FLL)
NK1339, NK0221, NK0335
19h 48min
Return
09/29/25
1 Stopover (GDL)
Q64058, Y41704
17h 52min
Spirit Airlines
$302
Best option
Chicago
San Jose, Costa Rica
Outbound
06/08/25
1 Stopover (MEX)
Y40701, Q64051
13h 17min
Return
06/12/25
1 Stopover (MEX)
Q64050, Y40700
13h 54min
Volaris, Volaris Costa Rica
$310
Chicago
San Jose, Costa Rica
Pay attention to transfer at connecting flight
Outbound
04/21/25
3 Stopovers (MCO, ATL, FLL)
NK0573, NK0211, NK0681, NK0335
27h 35min
Return
05/19/25
3 Stopovers (MCO, IAH, FLL)
NK1310, NK1576, NK0221, NK1026
26h 56min
Spirit Airlines
$365
Chicago
San Jose, Costa Rica
Outbound
06/20/25
1 Stopover (GUA)
AV0631, AV0651
08h 30min
Return
07/19/25
1 Stopover (DEN)
UA1087, UA2258
14h 50min
Avianca
$662
Chicago
San Jose, Costa Rica
Outbound
09/19/25
2 Stopovers (IAH, FLL)
NK1339, NK0221, NK0335
19h 48min
Return
09/29/25
1 Stopover (GDL)
Q64058, Y41704
17h 52min
Spirit Airlines
$304
Chicago
San Jose, Costa Rica
Outbound
09/19/25
1 Stopover (GDL)
Y41705, Q64059
12h 07min
Return
09/29/25
1 Stopover (GDL)
Q64058, Y41704
17h 52min
Volaris, Volaris Costa Rica ?
$335
Chicago
San Jose, Costa Rica
Outbound
04/21/25
3 Stopovers (MCO, ATL, FLL)
NK0573, NK0211, NK0442, NK0335
27h 35min
Return
05/19/25
2 Stopovers (MCO, IAH)
NK1310, NK1576, NK1145
21h 27min
Spirit Airlines ?
$339
Chicago
San Jose, Costa Rica
Outbound
06/20/25
1 Stopover (GUA)
AV0631, AV0651
08h 30min
Return
07/19/25
1 Stopover (GDL)
Q64058, Y41704
18h 33min
Avianca
$356
Chicago
San Jose, Costa Rica
Outbound
09/19/25
1 Stopover (GDL)
Y41705, Q64059
12h 07min
Return
09/29/25
1 Stopover (GDL)
Q64058, Y41704
17h 52min
Volaris, Volaris Costa Rica
$358
Chicago
San Jose, Costa Rica
Outbound
06/08/25
1 Stopover (FLL)
NK1986, NK0335
16h 58min
Return
06/29/25
1 Stopover (BOG)
AV0699, AV0262
19h 30min
Spirit Airlines ?
$380
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 $301.53
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 (ORD, MDW, RFD) (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