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 6 2017 Return: Tue Sep 12 2017 Trip spans 7 days
Delta
Delta
MDW
3:20a
SJU
9:52a
6h 32m
1 stop
SJU
10:14a
MDW
5:43p
7h 29m
1 stop
Depart: Thu Sep 7 2017 Return: Tue Sep 12 2017 Trip spans 6 days
Delta
Delta
MDW
8:00a
SJU
4:34p
8h 34m
1 stop
SJU
11:50a
MDW
7:48p
7h 58m
1 stop
Depart: Mon Sep 11 2017 Return: Tue Sep 19 2017 Trip spans 9 days
Delta
Delta
MDW
3:20a
SJU
9:52a
6h 32m
1 stop
SJU
3:25a
MDW
10:07a
6h 42m
1 stop
Depart: Tue Sep 12 2017 Return: Wed Sep 13 2017 Trip spans 2 days
Delta
Delta
MDW
2:00a
SJU
8:22a
6h 22m
1 stop
SJU
11:50a
MDW
7:53p
8h 03m
1 stop
Depart: Wed Sep 13 2017 Return: Tue Sep 19 2017 Trip spans 7 days
Delta
Delta
MDW
8:00a
SJU
4:34p
8h 34m
1 stop
SJU
11:50a
MDW
7:48p
7h 58m
1 stop
Depart: Thu Sep 14 2017 Return: Tue Sep 19 2017 Trip spans 6 days
Delta
Delta
MDW
9:40a
SJU
4:34p
6h 54m
1 stop
SJU
3:25a
MDW
10:07a
6h 42m
1 stop
Depart: Mon Oct 2 2017 Return: Wed Oct 11 2017 Trip spans 10 days
Delta
Delta
MDW
9:40a
SJU
4:34p
6h 54m
1 stop
SJU
11:50a
MDW
7:53p
8h 03m
1 stop
Depart: Tue Oct 3 2017 Return: Wed Oct 11 2017 Trip spans 9 days
Delta
Delta
MDW
2:00a
SJU
9:52a
7h 52m
1 stop
SJU
11:50a
MDW
7:53p
8h 03m
1 stop
Depart: Wed Oct 4 2017 Return: Wed Oct 11 2017 Trip spans 8 days
Delta
Delta
MDW
3:20a
SJU
9:52a
6h 32m
1 stop
SJU
10:14a
MDW
7:53p
9h 39m
1 stop
Depart: Tue Oct 10 2017 Return: Thu Oct 12 2017 Trip spans 3 days
Delta
Delta
MDW
9:40a
SJU
4:34p
6h 54m
1 stop
SJU
3:25a
MDW
10:07a
6h 42m
1 stop
Depart: Wed Oct 11 2017 Return: Thu Oct 12 2017 Trip spans 2 days
Delta
Delta
MDW
3:20a
SJU
9:52a
6h 32m
1 stop
SJU
11:50a
MDW
7:53p
8h 03m
1 stop
Depart: Mon Oct 16 2017 Return: Wed Oct 18 2017 Trip spans 3 days
Delta
Delta
MDW
9:40a
SJU
4:34p
6h 54m
1 stop
SJU
3:25a
MDW
12:22p
8h 57m
1 stop
Depart: Tue Oct 17 2017 Return: Tue Oct 24 2017 Trip spans 8 days
Delta
Delta
MDW
2:00a
SJU
9:52a
7h 52m
1 stop
SJU
11:50a
MDW
7:48p
7h 58m
1 stop
Depart: Wed Oct 18 2017 Return: Tue Oct 24 2017 Trip spans 7 days
Delta
Delta
MDW
9:40a
SJU
4:34p
6h 54m
1 stop
SJU
3:25a
MDW
10:07a
6h 42m
1 stop
Depart: Mon Oct 23 2017 Return: Tue Oct 31 2017 Trip spans 9 days
Delta
Delta
MDW
8:00a
SJU
4:34p
8h 34m
1 stop
SJU
11:50a
MDW
6:43p
6h 53m
1 stop
Depart: Tue Oct 24 2017 Return: Tue Oct 31 2017 Trip spans 8 days
Delta
Delta
MDW
9:40a
SJU
4:34p
6h 54m
1 stop
SJU
3:25a
MDW
10:07a
6h 42m
1 stop
Depart: Wed Oct 25 2017 Return: Tue Oct 31 2017 Trip spans 7 days
Delta
Delta
MDW
8:00a
SJU
4:34p
8h 34m
1 stop
SJU
11:50a
MDW
6:43p
6h 53m
1 stop
Depart: Sat Sep 16 2017 Return: Tue Sep 19 2017 Trip spans 4 days
Delta
Delta
MDW
1:10p
SJU
7:08a
17h 58m
2 stops
SJU
3:25a
MDW
12:22p
8h 57m
1 stop
Depart: Sat Oct 14 2017 Return: Tue Oct 17 2017 Trip spans 4 days
Delta
Delta
MDW
1:10p
SJU
7:08a
17h 58m
2 stops
SJU
11:50a
MDW
7:48p
7h 58m
1 stop
Depart: Tue Oct 31 2017 Return: Wed Nov 8 2017 Trip spans 9 days
Delta
Delta
MDW
3:20a
SJU
9:52a
6h 32m
1 stop
SJU
3:00a
MDW
7:53p
16h 53m
2 stops
* 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,
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Airports
Origin

Chicago
$362
Destination

San Juan
$362
Airlines