Find Deals on 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
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 Juan

(Round-trip)
Depart: Tue Jan 17 2017 Return: Fri Jan 20 2017 Trip spans 4 days
Delta
Delta
MDW
4:15a
SJU
5:30p
13h 15m
2 stops
SJU
2:40a
MDW
7:09p
16h 29m
2 stops
Depart: Wed Jan 18 2017 Return: Wed Jan 25 2017 Trip spans 8 days
Delta
Delta
MDW
4:24a
SJU
5:30p
13h 06m
2 stops
SJU
2:40a
MDW
5:02p
14h 22m
2 stops
Depart: Sat Jan 28 2017 Return: Wed Feb 1 2017 Trip spans 5 days
Delta
Delta
MDW
1:00a
SJU
12:52p
11h 52m
2 stops
SJU
2:40a
MDW
7:09p
16h 29m
2 stops
Depart: Tue Mar 28 2017 Return: Tue Apr 4 2017 Trip spans 8 days
Delta
Delta
MDW
2:25a
SJU
6:39p
16h 14m
2 stops
SJU
3:00a
MDW
5:02p
14h 02m
2 stops
Depart: Sat Jan 14 2017 Return: Fri Jan 20 2017 Trip spans 7 days
Delta
Delta
MDW
8:45a
SJU
3:34p
6h 49m
1 stop
SJU
2:40a
MDW
7:46p
17h 06m
2 stops
Depart: Sun Jan 15 2017 Return: Sat Jan 28 2017 Trip spans 14 days
Delta
Delta
MDW
7:20a
SJU
3:34p
8h 14m
1 stop
SJU
3:00a
MDW
7:07p
16h 07m
2 stops
Depart: Mon Jan 16 2017 Return: Tue Jan 24 2017 Trip spans 9 days
Delta
Delta
MDW
1:00a
SJU
7:19a
6h 19m
1 stop
SJU
2:40a
MDW
7:46p
17h 06m
2 stops
Depart: Thu Jan 19 2017 Return: Wed Jan 25 2017 Trip spans 7 days
Delta
Delta
MDW
1:00a
SJU
7:19a
6h 19m
1 stop
SJU
2:40a
MDW
7:46p
17h 06m
2 stops
Depart: Fri Jan 20 2017 Return: Tue Jan 24 2017 Trip spans 5 days
Delta
Delta
MDW
1:00a
SJU
7:19a
6h 19m
1 stop
SJU
2:40a
MDW
5:02p
14h 22m
2 stops
Depart: Sat Jan 21 2017 Return: Tue Jan 24 2017 Trip spans 4 days
Delta
Delta
MDW
8:45a
SJU
3:34p
6h 49m
1 stop
SJU
2:40a
MDW
5:02p
14h 22m
2 stops
Depart: Wed Jan 25 2017 Return: Tue Jan 31 2017 Trip spans 7 days
Delta
Delta
MDW
1:00a
SJU
12:56p
11h 56m
2 stops
SJU
10:21a
MDW
7:46p
9h 25m
1 stop
Depart: Fri Jan 27 2017 Return: Tue Jan 31 2017 Trip spans 5 days
Delta
Delta
MDW
9:08a
SJU
3:37p
6h 29m
1 stop
SJU
2:40a
MDW
7:46p
17h 06m
2 stops
Depart: Sun Feb 5 2017 Return: Wed Feb 15 2017 Trip spans 11 days
Delta
Delta
MDW
7:20a
SJU
3:34p
8h 14m
1 stop
SJU
2:40a
MDW
6:00p
15h 20m
2 stops
Depart: Wed Mar 1 2017 Return: Tue Mar 7 2017 Trip spans 7 days
Delta
Delta
MDW
2:05a
SJU
12:58p
10h 53m
2 stops
SJU
11:50a
MDW
7:13p
7h 23m
1 stop
Depart: Thu Mar 2 2017 Return: Tue Mar 7 2017 Trip spans 6 days
Delta
Delta
MDW
8:45a
SJU
3:34p
6h 49m
1 stop
SJU
3:00a
MDW
7:13p
16h 13m
2 stops
Depart: Wed Mar 8 2017 Return: Wed Mar 15 2017 Trip spans 7 days
Delta
Delta
MDW
1:00a
SJU
12:58p
11h 58m
2 stops
SJU
10:15a
MDW
7:07p
8h 52m
1 stop
Depart: Wed Mar 29 2017 Return: Wed Apr 5 2017 Trip spans 8 days
Delta
Delta
MDW
2:25a
SJU
6:39p
16h 14m
2 stops
SJU
10:14a
MDW
7:09p
8h 55m
1 stop
Depart: Sat Dec 31 2016 Return: Thu Jan 12 2017 Trip spans 13 days
Delta
Delta
MDW
10:26a
SJU
5:03p
6h 37m
1 stop
SJU
10:21a
MDW
7:46p
9h 25m
1 stop
Depart: Fri Jan 6 2017 Return: Thu Jan 12 2017 Trip spans 7 days
Delta
Delta
MDW
10:28a
SJU
5:05p
6h 37m
1 stop
SJU
10:21a
MDW
7:46p
9h 25m
1 stop
Depart: Tue Jan 10 2017 Return: Thu Jan 19 2017 Trip spans 10 days
Delta
Delta
MDW
1:00a
SJU
7:19a
6h 19m
1 stop
SJU
3:15a
MDW
10:33a
7h 18m
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
$343
Destination

San Juan
$343
Airlines