Find Deals on Flights from Chicago to Costa Rica

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
Students
under 26
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago to Costa Rica

(Round-trip)
Depart: Tue Jan 31 2017 Return: Wed Feb 8 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
SJO
10h 58m
1 stop
SJO
ORD
8h 55m
1 stop
Depart: Wed May 17 2017 Return: Wed May 24 2017 Trip spans 8 days
Avianca
Avianca
ORD
SJO
6h 55m
1 stop
SJO
ORD
6h 53m
1 stop
Depart: Mon Jan 23 2017 Return: Sat Jan 28 2017 Trip spans 6 days
Copa Airlines
Copa Airlines
ORD
SJO
13h 40m
1 stop
SJO
ORD
8h 55m
1 stop
Depart: Thu Jan 26 2017 Return: Tue Jan 31 2017 Trip spans 6 days
Delta
Delta
MDW
SJO
8h 41m
1 stop
SJO
MDW
8h 21m
1 stop
Depart: Thu Jul 20 2017 Return: Mon Jul 24 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
SJO
27h 43m
1 stop
SJO
ORD
24h 10m
1 stop
Depart: Mon Apr 24 2017 Return: Thu Apr 27 2017 Trip spans 4 days
United
United
ORD
LIR
17h 20m
2 stops
LIR
ORD
18h 12m
1 stop
Depart: Fri Mar 17 2017 Return: Sun Mar 26 2017 Trip spans 10 days
Aeromexico
Aeromexico
ORD
SJO
22h 52m
2 stops
SJO
ORD
18h 22m
2 stops
Depart: Mon Feb 13 2017 Return: Tue Mar 7 2017 Trip spans 23 days
Volaris
Volaris
MDW
SJO
18h 15m
1 stop
SJO
MDW
22h 02m
1 stop
Depart: Sun Feb 12 2017 Return: Mon Mar 6 2017 Trip spans 23 days
Major Airline
Major Airline
ORD
SJO
24h 23m
1 stop
SJO
ORD
14h 48m
1 stop
Depart: Thu Jun 8 2017 Return: Sun Jun 11 2017 Trip spans 4 days
Avianca
Avianca
ORD
SJO
6h 55m
1 stop
SJO
ORD
6h 53m
1 stop
Depart: Mon Mar 13 2017 Return: Mon Mar 20 2017 Trip spans 8 days
Copa Airlines
Copa Airlines
ORD
SJO
8h 31m
1 stop
SJO
ORD
29h 35m
1 stop
Depart: Fri Jan 27 2017 Return: Mon Feb 6 2017 Trip spans 11 days
Delta
Delta
MDW
SJO
8h 41m
1 stop
SJO
MDW
8h 21m
1 stop
Depart: Mon Mar 6 2017 Return: Mon Mar 13 2017 Trip spans 7 days
Major Airline
Major Airline
ORD
SJO
11h 35m
1 stop
SJO
ORD
15h 32m
1 stop
Depart: Mon Mar 20 2017 Return: Fri Mar 24 2017 Trip spans 5 days
Copa Airlines
Copa Airlines
ORD
SJO
25h 17m
1 stop
SJO
ORD
14h 48m
1 stop
Depart: Tue Mar 7 2017 Return: Thu Mar 23 2017 Trip spans 16 days
Delta
Delta
MDW
SJO
14h 55m
1 stop
SJO
MDW
12h 15m
1 stop
Depart: Tue Mar 14 2017 Return: Tue Mar 21 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SJO
8h 00m
1 stop
SJO
ORD
11h 45m
1 stop
Depart: Sat Jun 17 2017 Return: Tue Jun 20 2017 Trip spans 4 days
American Airlines
American Airlines
ORD
SJO
30h 42m
1 stop
SJO
ORD
25h 04m
1 stop
Depart: Wed Mar 15 2017 Return: Thu Mar 23 2017 Trip spans 9 days
Delta
Delta
MDW
SJO
7h 29m
1 stop
SJO
MDW
14h 10m
1 stop
Depart: Wed Mar 22 2017 Return: Mon Mar 27 2017 Trip spans 6 days
Major Airline
Major Airline
ORD
SJO
11h 35m
1 stop
SJO
ORD
18h 43m
1 stop
Depart: Wed Mar 15 2017 Return: Wed Mar 22 2017 Trip spans 8 days
Delta
Delta
MDW
SJO
7h 29m
1 stop
SJO
MDW
18h 13m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Chicago
only $276
only $298
Destination

Liberia
$441
San Jose
$276