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: Tue Sep 19 2017 Return: Wed Sep 27 2017 Trip spans 9 days
Delta
Delta
MDW
2:00a
SJU
9:35a
7h 35m
1 stop
SJU
9:05a
MDW
7:55p
10h 50m
2 stops
Depart: Mon Oct 2 2017 Return: Wed Oct 4 2017 Trip spans 3 days
Delta
Delta
MDW
3:20a
SJU
5:00p
13h 40m
2 stops
SJU
10:20a
MDW
7:40p
9h 20m
1 stop
Depart: Sun Oct 8 2017 Return: Sat Oct 14 2017 Trip spans 7 days
Delta
Delta
MDW
3:20a
SJU
9:31a
6h 11m
1 stop
SJU
3:06a
MDW
4:02p
12h 56m
2 stops
Depart: Wed Oct 11 2017 Return: Wed Oct 18 2017 Trip spans 8 days
Delta
Delta
MDW
3:00a
SJU
5:00p
14h 00m
2 stops
SJU
10:20a
MDW
7:40p
9h 20m
1 stop
Depart: Tue Oct 24 2017 Return: Thu Oct 26 2017 Trip spans 3 days
Delta
Delta
MDW
2:15a
SJU
5:00p
14h 45m
2 stops
SJU
3:15a
MDW
12:51p
9h 36m
1 stop
Depart: Tue Oct 31 2017 Return: Wed Nov 8 2017 Trip spans 9 days
Delta
Delta
MDW
3:20a
SJU
5:00p
13h 40m
2 stops
SJU
11:50a
MDW
7:53p
8h 03m
1 stop
Depart: Sat Jan 13 2018 Return: Fri Jan 19 2018 Trip spans 7 days
Delta
Delta
MDW
11:35a
SJU
6:08a
18h 33m
2 stops
SJU
3:00a
MDW
7:10p
16h 10m
2 stops
Depart: Tue Jan 16 2018 Return: Sat Jan 20 2018 Trip spans 5 days
Delta
Delta
MDW
1:00a
SJU
8:52a
7h 52m
1 stop
SJU
3:00a
MDW
7:13p
16h 13m
2 stops
Depart: Wed Jan 17 2018 Return: Tue Jan 23 2018 Trip spans 7 days
Delta
Delta
MDW
4:18a
SJU
4:24p
12h 06m
2 stops
SJU
3:00a
MDW
10:03a
7h 03m
1 stop
Depart: Thu Jan 18 2018 Return: Tue Jan 23 2018 Trip spans 6 days
Delta
Delta
MDW
8:40a
SJU
3:34p
6h 54m
1 stop
SJU
3:00a
MDW
6:08p
15h 08m
2 stops
Depart: Fri Jan 19 2018 Return: Wed Jan 24 2018 Trip spans 6 days
Delta
Delta
MDW
8:40a
SJU
3:34p
6h 54m
1 stop
SJU
9:10a
MDW
7:10p
10h 00m
2 stops
Depart: Sat Jan 20 2018 Return: Thu Jan 25 2018 Trip spans 6 days
Delta
Delta
MDW
11:35a
SJU
6:08a
18h 33m
2 stops
SJU
3:00a
MDW
12:25p
9h 25m
1 stop
Depart: Sun Jan 21 2018 Return: Fri Jan 26 2018 Trip spans 6 days
Delta
Delta
MDW
7:00a
SJU
3:34p
8h 34m
1 stop
SJU
9:10a
MDW
7:10p
10h 00m
2 stops
Depart: Mon Jan 22 2018 Return: Fri Jan 26 2018 Trip spans 5 days
Delta
Delta
MDW
4:18a
SJU
4:24p
12h 06m
2 stops
SJU
3:00a
MDW
6:08p
15h 08m
2 stops
Depart: Tue Jan 23 2018 Return: Sat Jan 27 2018 Trip spans 5 days
Delta
Delta
MDW
1:00a
SJU
4:24p
15h 24m
2 stops
SJU
3:00a
MDW
7:13p
16h 13m
2 stops
Depart: Wed Jan 24 2018 Return: Tue Jan 30 2018 Trip spans 7 days
Delta
Delta
MDW
1:00a
SJU
4:24p
15h 24m
2 stops
SJU
3:00a
MDW
6:08p
15h 08m
2 stops
Depart: Thu Jan 25 2018 Return: Tue Jan 30 2018 Trip spans 6 days
Delta
Delta
MDW
8:40a
SJU
3:34p
6h 54m
1 stop
SJU
9:10a
MDW
7:10p
10h 00m
2 stops
Depart: Sat Jan 27 2018 Return: Wed Jan 31 2018 Trip spans 5 days
Delta
Delta
MDW
1:00a
SJU
4:24p
15h 24m
2 stops
SJU
9:10a
MDW
7:10p
10h 00m
2 stops
Depart: Sun Jan 28 2018 Return: Thu Feb 1 2018 Trip spans 5 days
Delta
Delta
MDW
8:40a
SJU
3:34p
6h 54m
1 stop
SJU
9:10a
MDW
7:10p
10h 00m
2 stops
Depart: Mon Jan 29 2018 Return: Fri Feb 2 2018 Trip spans 5 days
Delta
Delta
MDW
1:00a
SJU
4:24p
15h 24m
2 stops
SJU
3:00a
MDW
7:10p
16h 10m
2 stops
* 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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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.

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Airports
Origin

Chicago
$389
Destination

San Juan
$389
Airlines