Find Cheap Flights from Chicago Midway to San Juan

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 San Juan

(Round-trip)
Depart: Wed Sep 27 2017 Return: Tue Oct 3 2017 Trip spans 7 days
Delta
Delta
MDW
3:20a
SJU
5:13p
13h 53m
2 stops
SJU
9:30a
MDW
8:02p
10h 32m
2 stops
Depart: Mon Oct 30 2017 Return: Tue Nov 7 2017 Trip spans 9 days
Delta
Delta
MDW
2:30a
SJU
5:24p
14h 54m
2 stops
SJU
3:00a
MDW
7:48p
16h 48m
2 stops
Depart: Tue Oct 31 2017 Return: Tue Nov 7 2017 Trip spans 8 days
Delta
Delta
MDW
2:00a
SJU
5:13p
15h 13m
2 stops
SJU
3:00a
MDW
7:48p
16h 48m
2 stops
Depart: Wed Nov 1 2017 Return: Tue Nov 7 2017 Trip spans 7 days
Delta
Delta
MDW
3:20a
SJU
5:13p
13h 53m
2 stops
SJU
3:00a
MDW
7:48p
16h 48m
2 stops
Depart: Tue Sep 5 2017 Return: Wed Sep 13 2017 Trip spans 9 days
Delta
Delta
MDW
10:05a
SJU
4:34p
6h 29m
1 stop
SJU
3:00a
MDW
8:07p
17h 07m
2 stops
Depart: Wed Sep 6 2017 Return: Wed Sep 13 2017 Trip spans 8 days
Delta
Delta
MDW
2:00a
SJU
8:22a
6h 22m
1 stop
SJU
3:00a
MDW
8:07p
17h 07m
2 stops
Depart: Tue Sep 12 2017 Return: Fri Sep 15 2017 Trip spans 4 days
Delta
Delta
MDW
3:20a
SJU
5:13p
13h 53m
2 stops
SJU
11:50a
MDW
8:07p
8h 17m
1 stop
Depart: Wed Sep 13 2017 Return: Fri Sep 15 2017 Trip spans 3 days
Delta
Delta
MDW
2:00a
SJU
5:13p
15h 13m
2 stops
SJU
10:14a
MDW
8:07p
9h 53m
1 stop
Depart: Sat Sep 16 2017 Return: Tue Sep 19 2017 Trip spans 4 days
Delta
Delta
MDW
1:10p
SJU
10:23a
21h 13m
2 stops
SJU
11:50a
MDW
8:02p
8h 12m
1 stop
Depart: Fri Sep 29 2017 Return: Wed Oct 4 2017 Trip spans 6 days
Delta
Delta
MDW
2:00a
SJU
9:52a
7h 52m
1 stop
SJU
9:30a
MDW
8:07p
10h 37m
2 stops
Depart: Sat Sep 30 2017 Return: Wed Oct 4 2017 Trip spans 5 days
Delta
Delta
MDW
2:00a
SJU
8:22a
6h 22m
1 stop
SJU
9:30a
MDW
8:07p
10h 37m
2 stops
Depart: Sun Oct 1 2017 Return: Wed Oct 4 2017 Trip spans 4 days
Delta
Delta
MDW
2:00a
SJU
9:52a
7h 52m
1 stop
SJU
9:30a
MDW
8:07p
10h 37m
2 stops
Depart: Mon Oct 2 2017 Return: Wed Oct 4 2017 Trip spans 3 days
Delta
Delta
MDW
2:00a
SJU
9:52a
7h 52m
1 stop
SJU
9:30a
MDW
8:07p
10h 37m
2 stops
Depart: Tue Oct 3 2017 Return: Wed Oct 4 2017 Trip spans 2 days
Delta
Delta
MDW
2:00a
SJU
8:22a
6h 22m
1 stop
SJU
9:30a
MDW
8:07p
10h 37m
2 stops
Depart: Tue Oct 17 2017 Return: Tue Oct 24 2017 Trip spans 8 days
Delta
Delta
MDW
3:20a
SJU
5:13p
13h 53m
2 stops
SJU
10:14a
MDW
8:02p
9h 48m
1 stop
Depart: Wed Oct 18 2017 Return: Wed Oct 25 2017 Trip spans 8 days
Delta
Delta
MDW
3:20a
SJU
5:13p
13h 53m
2 stops
SJU
11:50a
MDW
8:07p
8h 17m
1 stop
Depart: Sat Oct 21 2017 Return: Sat Oct 28 2017 Trip spans 8 days
Delta
Delta
MDW
2:30a
SJU
5:24p
14h 54m
2 stops
SJU
10:14a
MDW
8:05p
9h 51m
1 stop
Depart: Tue Oct 24 2017 Return: Tue Oct 31 2017 Trip spans 8 days
Delta
Delta
MDW
2:00a
SJU
5:13p
15h 13m
2 stops
SJU
3:25a
MDW
10:07a
6h 42m
1 stop
Depart: Sat Nov 11 2017 Return: Wed Nov 15 2017 Trip spans 5 days
Delta
Delta
MDW
5:10a
SJU
4:24p
11h 14m
2 stops
SJU
11:50a
MDW
7:53p
8h 03m
1 stop
Depart: Wed Nov 15 2017 Return: Sun Dec 3 2017 Trip spans 19 days
Delta
Delta
MDW
2:20a
SJU
4:24p
14h 04m
2 stops
SJU
3:00a
MDW
12:22p
9h 22m
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
$379
Destination

San Juan
$379
Airlines