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: Wed Sep 27 2017 Return: Mon Oct 2 2017 Trip spans 6 days
Delta
Delta
MDW
2:00a
SJO
8:49a
6h 49m
1 stop
SJO
3:20a
MDW
6:07p
14h 47m
1 stop
Depart: Thu Jan 11 2018 Return: Sun Jan 21 2018 Trip spans 11 days
Hahn Air Systems
Hahn Air Systems
MDW
12:29p
SJO
2:25p
25h 56m
1 stop
SJO
6:11a
MDW
5:57a
23h 46m
1 stop
Depart: Wed Oct 4 2017 Return: Wed Nov 1 2017 Trip spans 29 days
Delta
Delta
MDW
8:00a
SJO
4:40p
8h 40m
1 stop
SJO
9:00a
MDW
4:43p
7h 43m
1 stop
Depart: Thu Oct 5 2017 Return: Mon Oct 9 2017 Trip spans 5 days
Delta
Delta
MDW
3:20a
SJO
4:40p
13h 20m
1 stop
SJO
3:20a
MDW
6:07p
14h 47m
1 stop
Depart: Tue Oct 10 2017 Return: Mon Oct 16 2017 Trip spans 7 days
Delta
Delta
MDW
2:00a
SJO
8:46a
6h 46m
1 stop
SJO
3:20a
MDW
4:03p
12h 43m
1 stop
Depart: Wed Oct 11 2017 Return: Mon Oct 16 2017 Trip spans 6 days
Delta
Delta
MDW
8:00a
SJO
4:40p
8h 40m
1 stop
SJO
9:00a
MDW
6:07p
9h 07m
1 stop
Depart: Wed Oct 18 2017 Return: Tue Oct 24 2017 Trip spans 7 days
Delta
Delta
MDW
10:10a
SJO
4:40p
6h 30m
1 stop
SJO
3:20a
MDW
10:46a
7h 26m
1 stop
Depart: Tue Sep 5 2017 Return: Wed Sep 13 2017 Trip spans 9 days
Hahn Air Systems
Hahn Air Systems
MDW
1:30p
SJO
4:25p
26h 55m
1 stop
SJO
7:11a
MDW
6:15a
23h 04m
1 stop
Depart: Thu Oct 19 2017 Return: Mon Oct 23 2017 Trip spans 5 days
Delta
Delta
MDW
3:20a
SJO
4:40p
13h 20m
1 stop
SJO
9:00a
MDW
6:07p
9h 07m
1 stop
Depart: Sun Dec 3 2017 Return: Sun Dec 10 2017 Trip spans 8 days
Hahn Air Systems
Hahn Air Systems
MDW
12:29p
SJO
2:25p
25h 56m
1 stop
SJO
6:11a
MDW
5:57a
23h 46m
1 stop
Depart: Tue Oct 24 2017 Return: Tue Oct 31 2017 Trip spans 8 days
Delta
Delta
MDW
2:00a
SJO
8:46a
6h 46m
1 stop
SJO
3:20a
MDW
12:22p
9h 02m
1 stop
Depart: Sun Sep 17 2017 Return: Mon Sep 25 2017 Trip spans 9 days
Hahn Air Systems
Hahn Air Systems
MDW
1:30p
SJO
4:25p
26h 55m
1 stop
SJO
7:11a
MDW
6:15a
23h 04m
1 stop
Depart: Mon Nov 6 2017 Return: Thu Nov 9 2017 Trip spans 4 days
Delta
Delta
MDW
1:00a
SJO
7:46a
6h 46m
1 stop
SJO
3:05a
MDW
4:03p
12h 58m
1 stop
Depart: Sat Nov 18 2017 Return: Wed Nov 22 2017 Trip spans 5 days
Hahn Air Systems
Hahn Air Systems
MDW
12:29p
SJO
2:25p
25h 56m
1 stop
SJO
6:11a
MDW
5:57a
23h 46m
1 stop
Depart: Tue Dec 5 2017 Return: Wed Dec 20 2017 Trip spans 16 days
Delta
Delta
MDW
1:00a
SJO
7:46a
6h 46m
1 stop
SJO
9:00a
MDW
5:53p
8h 53m
1 stop
Depart: Thu Nov 2 2017 Return: Mon Nov 6 2017 Trip spans 5 days
Hahn Air Systems
Hahn Air Systems
MDW
1:29p
SJO
4:25p
26h 56m
1 stop
SJO
6:11a
MDW
5:57a
23h 46m
1 stop
Depart: Thu Sep 14 2017 Return: Sun Sep 17 2017 Trip spans 4 days
Delta
Delta
MDW
2:00a
SJO
8:49a
6h 49m
1 stop
SJO
9:04a
MDW
5:55p
8h 51m
1 stop
Depart: Sun Jan 14 2018 Return: Sun Jan 21 2018 Trip spans 8 days
Hahn Air Systems
Hahn Air Systems
MDW
12:29p
SJO
2:25p
25h 56m
1 stop
SJO
6:11a
MDW
5:57a
23h 46m
1 stop
Depart: Mon Oct 16 2017 Return: Sat Oct 28 2017 Trip spans 13 days
Delta
Delta
MDW
2:00a
SJO
8:46a
6h 46m
1 stop
SJO
3:20a
MDW
6:05p
14h 45m
1 stop
Depart: Thu Sep 28 2017 Return: Sun Oct 1 2017 Trip spans 4 days
Hahn Air Systems
Hahn Air Systems
MDW
1:30p
SJO
4:25p
26h 55m
1 stop
SJO
7:11a
MDW
6:15a
23h 04m
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
$408
Destination

San Jose
$408