Find Cheap Flights from Chicago Midway 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
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Chicago Midway to Costa Rica

(Round-trip)
Depart: Sat Apr 29 2017 Return: Wed May 3 2017 Trip spans 5 days
Delta
Delta
MDW
3:20a
SJO
10:03a
6h 43m
1 stop
SJO
9:00a
MDW
5:20p
8h 20m
1 stop
Depart: Thu Aug 24 2017 Return: Mon Aug 28 2017 Trip spans 5 days
Volaris
Volaris
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Tue May 2 2017 Return: Wed May 17 2017 Trip spans 16 days
Delta
Delta
MDW
10:10a
SJO
5:07p
6h 57m
1 stop
SJO
3:05a
MDW
12:17p
9h 12m
1 stop
Depart: Thu May 11 2017 Return: Mon May 15 2017 Trip spans 5 days
Delta
Delta
MDW
3:20a
SJO
5:07p
13h 47m
1 stop
SJO
3:05a
MDW
3:00p
11h 55m
1 stop
Depart: Fri May 12 2017 Return: Mon May 15 2017 Trip spans 4 days
Delta
Delta
MDW
3:20a
SJO
5:07p
13h 47m
1 stop
SJO
3:05a
MDW
5:20p
14h 15m
1 stop
Depart: Wed May 3 2017 Return: Wed May 10 2017 Trip spans 8 days
Delta
Delta
MDW
8:05a
SJO
5:07p
9h 02m
1 stop
SJO
9:00a
MDW
5:20p
8h 20m
1 stop
Depart: Tue Aug 29 2017 Return: Wed Sep 6 2017 Trip spans 9 days
Volaris
Volaris
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Mon May 29 2017 Return: Fri Jun 2 2017 Trip spans 5 days
Delta
Delta
MDW
3:20a
SJO
5:07p
13h 47m
1 stop
SJO
3:05a
MDW
3:00p
11h 55m
1 stop
Depart: Sun Sep 24 2017 Return: Sun Oct 8 2017 Trip spans 15 days
Volaris
Volaris
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Thu Jun 1 2017 Return: Thu Jun 8 2017 Trip spans 8 days
Delta
Delta
MDW
8:05a
SJO
5:07p
9h 02m
1 stop
SJO
3:05a
MDW
12:17p
9h 12m
1 stop
Depart: Tue Oct 17 2017 Return: Mon Oct 30 2017 Trip spans 14 days
Volaris
Volaris
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Thu Oct 26 2017 Return: Mon Oct 30 2017 Trip spans 5 days
Volaris
Volaris
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Wed May 10 2017 Return: Sat May 20 2017 Trip spans 11 days
Delta
Delta
MDW
8:05a
SJO
5:07p
9h 02m
1 stop
SJO
3:05a
MDW
12:15p
9h 10m
1 stop
Depart: Sat May 20 2017 Return: Fri Jun 2 2017 Trip spans 14 days
Delta
Delta
MDW
2:00a
SJO
10:03a
8h 03m
1 stop
SJO
3:05a
MDW
5:20p
14h 15m
1 stop
Depart: Tue Aug 22 2017 Return: Wed Aug 30 2017 Trip spans 9 days
Volaris
Volaris
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Wed May 24 2017 Return: Wed Jun 7 2017 Trip spans 15 days
Delta
Delta
MDW
8:05a
SJO
5:07p
9h 02m
1 stop
SJO
3:05a
MDW
5:20p
14h 15m
1 stop
Depart: Sun Oct 8 2017 Return: Sun Oct 15 2017 Trip spans 8 days
Volaris
Volaris
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Thu May 25 2017 Return: Mon Jun 5 2017 Trip spans 12 days
Volaris
Volaris
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Tue May 16 2017 Return: Thu May 18 2017 Trip spans 3 days
Delta
Delta
MDW
8:05a
SJO
5:07p
9h 02m
1 stop
SJO
9:00a
MDW
5:20p
8h 20m
1 stop
Depart: Thu Aug 31 2017 Return: Mon Sep 4 2017 Trip spans 5 days
Volaris
Volaris
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
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.

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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
$298
Destination

San Jose
$298