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: Fri Jan 20 2017 Return: Fri Jan 27 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SJO
9h 37m
1 stop
SJO
ORD
10h 23m
1 stop
Depart: Thu Apr 27 2017 Return: Fri Apr 28 2017 Trip spans 2 days
JetBlue
JetBlue
ORD
SJO
7h 24m
1 stop
SJO
ORD
9h 35m
1 stop
Depart: Sat Apr 8 2017 Return: Sat Apr 15 2017 Trip spans 8 days
United
United
ORD
SJO
5h 15m
nonstop
SJO
ORD
5h 35m
nonstop
Depart: Thu Feb 9 2017 Return: Sat Feb 18 2017 Trip spans 10 days
Copa Airlines
Copa Airlines
ORD
SJO
8h 34m
1 stop
SJO
ORD
10h 32m
1 stop
Depart: Thu Feb 9 2017 Return: Tue Feb 14 2017 Trip spans 6 days
Delta
Delta
MDW
SJO
6h 53m
1 stop
SJO
MDW
9h 12m
1 stop
Depart: Mon Apr 3 2017 Return: Fri Apr 7 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
SJO
7h 37m
1 stop
SJO
ORD
25h 04m
1 stop
Depart: Fri Feb 3 2017 Return: Fri Feb 10 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SJO
25h 16m
1 stop
SJO
ORD
15h 07m
1 stop
Depart: Thu Jun 29 2017 Return: Tue Jul 4 2017 Trip spans 6 days
Avianca
Avianca
ORD
LIR
25h 28m
1 stop
LIR
ORD
19h 38m
1 stop
Depart: Wed Feb 22 2017 Return: Sun Feb 26 2017 Trip spans 5 days
Volaris
Volaris
MDW
SJO
18h 15m
1 stop
SJO
MDW
22h 02m
1 stop
Depart: Mon May 1 2017 Return: Mon May 8 2017 Trip spans 8 days
JetBlue
JetBlue
ORD
SJO
7h 24m
1 stop
SJO
ORD
9h 01m
1 stop
Depart: Mon Feb 13 2017 Return: Tue Mar 14 2017 Trip spans 29 days
Delta
Delta
MDW
SJO
7h 07m
1 stop
SJO
MDW
9h 18m
1 stop
Depart: Tue May 30 2017 Return: Mon Jun 5 2017 Trip spans 7 days
Copa Airlines
Copa Airlines
ORD
SJO
7h 50m
1 stop
SJO
ORD
10h 29m
1 stop
Depart: Thu Apr 27 2017 Return: Sat May 6 2017 Trip spans 10 days
Major Airline
Major Airline
ORD
SJO
25h 30m
1 stop
SJO
ORD
7h 00m
1 stop
Depart: Thu Mar 2 2017 Return: Sun Mar 5 2017 Trip spans 4 days
United
United
ORD
SJO
8h 50m
1 stop
SJO
ORD
29h 58m
1 stop
Depart: Tue Feb 14 2017 Return: Wed Mar 15 2017 Trip spans 29 days
Delta
Delta
MDW
SJO
15h 01m
1 stop
SJO
MDW
8h 07m
1 stop
Depart: Tue Feb 28 2017 Return: Tue Mar 14 2017 Trip spans 14 days
Delta
Delta
MDW
SJO
6h 55m
1 stop
SJO
MDW
9h 18m
1 stop
Depart: Sat Mar 18 2017 Return: Sun Mar 26 2017 Trip spans 9 days
Copa Airlines
Copa Airlines
ORD
SJO
7h 50m
1 stop
SJO
ORD
8h 45m
1 stop
Depart: Thu Mar 30 2017 Return: Sat Apr 8 2017 Trip spans 10 days
Major Airline
Major Airline
ORD
SJO
12h 25m
1 stop
SJO
ORD
9h 55m
1 stop
Depart: Sat Mar 4 2017 Return: Sat Mar 11 2017 Trip spans 8 days
United
United
ORD
SJO
5h 15m
nonstop
SJO
ORD
5h 35m
nonstop
Depart: Mon Mar 6 2017 Return: Wed Mar 15 2017 Trip spans 9 days
Delta
Delta
MDW
SJO
8h 25m
1 stop
SJO
MDW
8h 07m
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 $260
only $350
Destination

Liberia
$543
San Jose
$260