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
Pay attention to transfer at connecting flight
Outbound
11/09/25
1 Stopover (MCO)
NK1880, Q64001
28h 58min
Return
12/07/25
1 Stopover (MCO)
Q64000, NK2530
13h 53min
Spirit Airlines, Volaris Costa Rica
$302
Best option
Chicago
San Jose, Costa Rica
Outbound
11/09/25
direct
AA0353
05h 00min
Return
12/07/25
direct
AA0326
05h 31min
American Airlines ?
$402
Chicago
San Jose, Costa Rica
Outbound
11/09/25
1 Stopover (FLL)
NK0002, NK0335
07h 09min
Return
12/07/25
1 Stopover (FLL)
NK1756, NK1986
08h 07min
Spirit Airlines
$330
Chicago
San Jose, Costa Rica
Outbound
11/09/25
1 Stopover (PTY)
CM0229, CM0344
18h 58min
Return
12/07/25
1 Stopover (FLL)
NK0338, NK0001
10h 23min
Copa Airlines ?
$347
Chicago
San Jose, Costa Rica
Outbound
11/09/25
1 Stopover (PTY)
CM0229, CM0818
18h 12min
Return
12/07/25
1 Stopover (ATL)
DL1756, DL1199
09h 30min
Copa Airlines ?
$367
Chicago
San Jose, Costa Rica
Outbound
11/09/25
1 Stopover (PTY)
CM0229, CM0344
18h 58min
Return
12/07/25
direct
AA0326
05h 31min
Copa Airlines ?
$476
Chicago
San Jose, Costa Rica
Outbound
11/09/25
1 Stopover (PTY)
CM0229, CM0344
18h 58min
Return
12/07/25
1 Stopover (PTY)
CM0465, CM0228
31h 03min
Copa Airlines ?
$641
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
1 Stopover (ATL)
F91596, F90215
08h 26min
Return
12/30/25
1 Stopover (FLL)
NK0338, NK3153
07h 41min
Frontier Airlines ?
$720
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
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 $173.00 more expensive than flights with a stopover.
non stop flight
1 stop
2 stops
06h 45min
25h 29min
15h 50min
452 US$
279 US$
352 US$
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 US$
35 %
1 stopover Houston - George Bush Intercontinental Airport, TX
13h 56min, from 311 US$
23 %
1 stopover Mexico City-Juarez International
17h 13min, from 634 US$
12 %

Important flight information

Flight information: Chicago - San Jose, Costa Rica

Roundtrip from 301,13 US$
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