Find Deals on Flights from Chicago Midway to San Jose Juan Santamaria Intl (MDW - SJO)

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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Book cheap flights from Chicago Midway to San Jose Juan Santamaria Intl

(Round-trip)
Depart: Mon Feb 6 2017 Return: Sat Feb 11 2017 Trip spans 6 days
Delta
Delta
MDW
1:00a
SJO
8:07a
7h 07m
1 stop
SJO
3:10a
MDW
12:19p
9h 09m
1 stop
Depart: Wed Apr 12 2017 Return: Sun Apr 16 2017 Trip spans 5 days
Major Airline
Major Airline
MDW
11:05p
SJO
2:45p
15h 40m
1 stop
SJO
5:00a
MDW
1:09p
8h 09m
1 stop
Depart: Sun May 14 2017 Return: Sun May 28 2017 Trip spans 15 days
Volaris
Volaris
MDW
1:29p
SJO
8:19a
18h 50m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Mon Feb 13 2017 Return: Tue Mar 28 2017 Trip spans 43 days
Delta
Delta
MDW
1:00a
SJO
8:07a
7h 07m
1 stop
SJO
9:00a
MDW
5:07p
8h 07m
1 stop
Depart: Tue Feb 14 2017 Return: Tue Mar 28 2017 Trip spans 42 days
Delta
Delta
MDW
5:30a
SJO
4:01p
10h 31m
1 stop
SJO
9:00a
MDW
5:07p
8h 07m
1 stop
Depart: Wed Mar 15 2017 Return: Wed Mar 22 2017 Trip spans 8 days
Delta
Delta
MDW
2:00a
SJO
8:46a
6h 46m
1 stop
SJO
3:20a
MDW
3:02p
11h 42m
1 stop
Depart: Sun Mar 19 2017 Return: Tue Mar 28 2017 Trip spans 10 days
Delta
Delta
MDW
3:05a
SJO
4:40p
13h 35m
1 stop
SJO
9:00a
MDW
5:07p
8h 07m
1 stop
Depart: Mon Mar 20 2017 Return: Wed Mar 22 2017 Trip spans 3 days
Delta
Delta
MDW
2:00a
SJO
10:04a
8h 04m
1 stop
SJO
3:20a
MDW
5:07p
13h 47m
1 stop
Depart: Wed Mar 29 2017 Return: Sun Apr 2 2017 Trip spans 5 days
Volaris
Volaris
MDW
2:50p
SJO
9:05a
18h 15m
1 stop
SJO
8:25a
MDW
5:57a
21h 32m
1 stop
Depart: Tue Mar 21 2017 Return: Thu Mar 23 2017 Trip spans 3 days
Delta
Delta
MDW
2:00a
SJO
10:04a
8h 04m
1 stop
SJO
3:20a
MDW
12:38p
9h 18m
1 stop
Depart: Wed Jan 11 2017 Return: Thu Feb 16 2017 Trip spans 37 days
Volaris
Volaris
MDW
1:06p
SJO
7:05a
17h 59m
1 stop
SJO
8:25a
MDW
6:27a
22h 02m
1 stop
Depart: Wed Mar 22 2017 Return: Tue Mar 28 2017 Trip spans 7 days
Delta
Delta
MDW
3:05a
SJO
10:04a
6h 59m
1 stop
SJO
9:00a
MDW
5:07p
8h 07m
1 stop
Depart: Tue May 2 2017 Return: Fri May 12 2017 Trip spans 11 days
Volaris
Volaris
MDW
1:29p
SJO
8:19a
18h 50m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Sun Mar 26 2017 Return: Tue Mar 28 2017 Trip spans 3 days
Delta
Delta
MDW
8:15a
SJO
4:40p
8h 25m
1 stop
SJO
9:00a
MDW
5:07p
8h 07m
1 stop
Depart: Mon Mar 27 2017 Return: Tue Mar 28 2017 Trip spans 2 days
Delta
Delta
MDW
2:00a
SJO
8:46a
6h 46m
1 stop
SJO
9:00a
MDW
5:07p
8h 07m
1 stop
Depart: Sat Mar 11 2017 Return: Sun Mar 19 2017 Trip spans 8 days
Volaris
Volaris
MDW
12:50p
SJO
8:05a
18h 15m
1 stop
SJO
9:25a
MDW
7:27a
22h 02m
1 stop
Depart: Mon Apr 3 2017 Return: Thu Apr 20 2017 Trip spans 18 days
Delta
Delta
MDW
9:45a
SJO
4:40p
6h 55m
1 stop
SJO
3:20a
MDW
3:02p
11h 42m
1 stop
Depart: Sat Mar 4 2017 Return: Sun Mar 12 2017 Trip spans 8 days
Volaris
Volaris
MDW
12:50p
SJO
7:05a
18h 15m
1 stop
SJO
9:25a
MDW
7:27a
22h 02m
1 stop
Depart: Fri Apr 21 2017 Return: Tue Apr 25 2017 Trip spans 5 days
Delta
Delta
MDW
8:15a
SJO
4:40p
8h 25m
1 stop
SJO
3:20a
MDW
3:02p
11h 42m
1 stop
Depart: Sat Feb 18 2017 Return: Sun Feb 26 2017 Trip spans 9 days
Volaris
Volaris
MDW
12:50p
SJO
7:05a
18h 15m
1 stop
SJO
8:25a
MDW
6:27a
22h 02m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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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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.

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Airports
Origin

Chicago
$350
Destination

San Jose
$350