Find Cheap Flights from Chicago to Costa Rica

Depart
Return
1 adult
Cabin Economy
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
Close
The price shown for each flight will be the average for all passengers including any infants.
Show flexible dates
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

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 Oct 31 2017 Return: Tue Nov 7 2017 Trip spans 8 days
$305
Select
Multiple Airlines
Multiple Airlines
ORD
→
SJO
18h 19m
1 stop
SJO
→
ORD
8h 21m
1 stop
Depart: Tue Oct 3 2017 Return: Tue Oct 10 2017 Trip spans 8 days
$310
Select
Spirit Airlines
Spirit Airlines
ORD
→
SJO
7h 20m
1 stop
SJO
→
ORD
10h 23m
1 stop
Depart: Wed Oct 18 2017 Return: Thu Oct 26 2017 Trip spans 9 days
$336
Select
Interjet
Interjet
ORD
→
SJO
9h 55m
1 stop
SJO
→
ORD
10h 10m
1 stop
Depart: Sun Feb 11 2018 Return: Wed Feb 21 2018 Trip spans 11 days
$360
Select
JetBlue
JetBlue
ORD
→
SJO
7h 24m
1 stop
SJO
→
ORD
8h 18m
1 stop
Depart: Tue Oct 24 2017 Return: Tue Oct 31 2017 Trip spans 8 days
$310
Select
Spirit Airlines
Spirit Airlines
ORD
→
SJO
7h 56m
1 stop
SJO
→
ORD
10h 23m
1 stop
Depart: Tue Oct 10 2017 Return: Fri Oct 13 2017 Trip spans 4 days
$323
Select
Multiple Airlines
Multiple Airlines
ORD
→
SJO
7h 20m
1 stop
SJO
→
ORD
9h 23m
1 stop
Depart: Mon Oct 23 2017 Return: Sun Oct 29 2017 Trip spans 7 days
$336
Select
Interjet
Interjet
ORD
→
SJO
22h 15m
1 stop
SJO
→
ORD
20h 10m
1 stop
Depart: Sat Nov 11 2017 Return: Tue Nov 14 2017 Trip spans 4 days
$310
Select
Spirit Airlines
Spirit Airlines
ORD
→
SJO
6h 50m
1 stop
SJO
→
ORD
8h 50m
1 stop
Depart: Wed Oct 11 2017 Return: Wed Oct 25 2017 Trip spans 15 days
$323
Select
Multiple Airlines
Multiple Airlines
ORD
→
SJO
7h 20m
1 stop
SJO
→
ORD
9h 23m
1 stop
Depart: Mon Feb 12 2018 Return: Thu Feb 15 2018 Trip spans 4 days
$360
Select
JetBlue
JetBlue
ORD
→
SJO
7h 24m
1 stop
SJO
→
ORD
8h 18m
1 stop
Depart: Wed Oct 25 2017 Return: Sat Oct 28 2017 Trip spans 4 days
$336
Select
Interjet
Interjet
ORD
→
SJO
23h 35m
1 stop
SJO
→
ORD
16h 25m
1 stop
Depart: Sat Oct 28 2017 Return: Thu Nov 2 2017 Trip spans 6 days
$315
Select
Spirit Airlines
Spirit Airlines
ORD
→
SJO
7h 56m
1 stop
SJO
→
ORD
10h 23m
1 stop
Depart: Tue Oct 31 2017 Return: Tue Nov 7 2017 Trip spans 8 days
$323
Select
Multiple Airlines
Multiple Airlines
ORD
→
SJO
7h 56m
1 stop
SJO
→
ORD
8h 21m
1 stop
Depart: Tue Oct 17 2017 Return: Tue Oct 24 2017 Trip spans 8 days
$319
Select
Spirit Airlines
Spirit Airlines
ORD
→
SJO
7h 20m
1 stop
SJO
→
ORD
10h 23m
1 stop
Depart: Mon Oct 23 2017 Return: Thu Oct 26 2017 Trip spans 4 days
$327
Select
Multiple Airlines
Multiple Airlines
ORD
→
SJO
12h 04m
2 stops
SJO
→
ORD
12h 44m
2 stops
Depart: Sat Oct 21 2017 Return: Tue Oct 24 2017 Trip spans 4 days
$319
Select
Spirit Airlines
Spirit Airlines
ORD
→
SJO
7h 56m
1 stop
SJO
→
ORD
10h 23m
1 stop
Depart: Tue Oct 17 2017 Return: Mon Oct 23 2017 Trip spans 7 days
$340
Select
Multiple Airlines
Multiple Airlines
ORD
→
SJO
7h 56m
1 stop
SJO
→
ORD
16h 25m
1 stop
Depart: Wed Nov 29 2017 Return: Fri Dec 8 2017 Trip spans 10 days
$321
Select
Spirit Airlines
Spirit Airlines
ORD
→
SJO
7h 35m
1 stop
SJO
→
ORD
8h 50m
1 stop
Depart: Sat Oct 21 2017 Return: Sat Oct 28 2017 Trip spans 8 days
$340
Select
Multiple Airlines
Multiple Airlines
ORD
→
SJO
7h 56m
1 stop
SJO
→
ORD
16h 25m
1 stop
Depart: Tue Nov 14 2017 Return: Wed Nov 29 2017 Trip spans 16 days
$324
Select
Spirit Airlines
Spirit Airlines
ORD
→
SJO
7h 35m
1 stop
SJO
→
ORD
8h 50m
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.

^ The fares displayed in KAYAK ads found on other sites include all taxes and fees for economy class travel and were found by KAYAK users in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.
Airports
Origin
Chicago
$305
Destination
San Jose
$305