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
10/10/25
1 Stopover (ATL)
F93398, F90215
27h 18min
Return
11/04/25
1 Stopover (MEX)
Q64050, Y40700
13h 54min
Frontier Airlines
$305
Best option
Chicago
San Jose, Costa Rica
Outbound
10/10/25
1 Stopover (MIA)
AA0534, AA0597
08h 00min
Return
11/04/25
direct
AA0314
05h 38min
American Airlines ?
$481
Chicago
San Jose, Costa Rica
Outbound
10/10/25
1 Stopover (ATL)
F93398, F90215
27h 18min
Return
11/04/25
1 Stopover (MEX)
Q64050, Y40700
13h 54min
Frontier Airlines
$319
Chicago
San Jose, Costa Rica
Outbound
10/10/25
1 Stopover (ATL)
F91442, F90215
19h 13min
Return
11/04/25
1 Stopover (JFK)
B61794, B62105
15h 09min
Frontier Airlines ?
$356
Chicago
San Jose, Costa Rica
Outbound
10/10/25
1 Stopover (MIA)
AA0534, AA0597
08h 00min
Return
11/04/25
direct
AA0314
05h 38min
American Airlines ?
$485
Chicago
San Jose, Costa Rica
Outbound
10/10/25
1 Stopover (MIA)
AA0534, AA0597
08h 00min
Return
11/04/25
direct
AA0314
05h 38min
American Airlines ?
$540
Chicago
San Jose, Costa Rica
Outbound
10/10/25
1 Stopover (YUL)
AC8958, AC0959
12h 45min
Return
11/04/25
1 Stopover (YYZ)
AC0956, AC0509
10h 37min
Air Canada ?
$601
Chicago
San Jose, Costa Rica
Outbound
12/19/25
1 Stopover (IAH)
UA2665, UA1280
23h 16min
Return
12/30/25
1 Stopover (IAH)
UA1447, UA2197
12h 41min
United Airlines ?
$710
Chicago
San Jose, Costa Rica
Outbound
12/19/25
2 Stopovers (MSP, MCO)
SY0262, SY0341, Q64001
19h 38min
Return
12/30/25
1 Stopover (FLL)
NK0338, NK0001
10h 23min
Sun Country Airlines, Volaris Costa Rica
$742
Chicago
San Jose, Costa Rica
Outbound
10/10/25
1 Stopover (FLL)
NK0019, NK0335
07h 13min
Return
11/04/25
1 Stopover (MEX)
AM0657, AM0682
17h 00min
Spirit Airlines
$746
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 304,77 $
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