Find Cheap Flights from Puerto Rico to Chicago Midway

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 Puerto Rico to Chicago Midway

(Round-trip)
Depart: Fri Nov 3 2017 Return: Sun Nov 5 2017 Trip spans 3 days
Delta
Delta
SJU
12:00a
MDW
10:45a
10h 45m
2 stops
MDW
12:00a
SJU
5:32a
6h 32m
1 stop
Depart: Fri Oct 13 2017 Return: Thu Oct 19 2017 Trip spans 7 days
Multiple Airlines
Multiple Airlines
SJU
12:00a
MDW
5:47p
17h 47m
2 stops
MDW
12:00a
SJU
7:38a
7h 38m
1 stop
Depart: Wed Sep 13 2017 Return: Wed Sep 27 2017 Trip spans 15 days
Delta
Delta
SJU
12:00a
MDW
9:35a
9h 35m
1 stop
MDW
12:00a
SJU
7:35a
7h 35m
1 stop
Depart: Thu Sep 21 2017 Return: Tue Sep 26 2017 Trip spans 6 days
Delta
Delta
SJU
12:00a
MDW
8:25a
8h 25m
1 stop
MDW
12:00a
SJU
6:10a
6h 10m
1 stop
Depart: Sat Sep 23 2017 Return: Tue Sep 26 2017 Trip spans 4 days
Delta
Delta
SJU
12:00a
MDW
9:23a
9h 23m
1 stop
MDW
12:00a
SJU
8:50a
8h 50m
1 stop
Depart: Sat Oct 14 2017 Return: Mon Oct 16 2017 Trip spans 3 days
Multiple Airlines
Multiple Airlines
SJU
12:00a
MDW
12:44p
12h 44m
2 stops
MDW
12:00a
SJU
1:47a
25h 47m
2 stops
Depart: Tue Sep 26 2017 Return: Mon Oct 2 2017 Trip spans 7 days
Delta
Delta
SJU
12:00a
MDW
7:16a
7h 16m
1 stop
MDW
12:00a
SJU
6:11a
6h 11m
1 stop
Depart: Thu Sep 28 2017 Return: Sun Oct 1 2017 Trip spans 4 days
Delta
Delta
SJU
12:00a
MDW
6:21a
6h 21m
1 stop
MDW
12:00a
SJU
6:11a
6h 11m
1 stop
Depart: Fri Nov 10 2017 Return: Mon Nov 13 2017 Trip spans 4 days
Delta
Delta
SJU
12:00a
MDW
8:17a
8h 17m
1 stop
MDW
12:00a
SJU
6:37a
6h 37m
1 stop
Depart: Sat Oct 14 2017 Return: Wed Oct 18 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
SJU
12:00a
MDW
12:10p
12h 10m
2 stops
MDW
12:00a
SJU
3:21a
27h 21m
1 stop
Depart: Thu Sep 14 2017 Return: Wed Sep 27 2017 Trip spans 14 days
Delta
Delta
SJU
12:00a
MDW
8:25a
8h 25m
1 stop
MDW
12:00a
SJU
11:54a
11h 54m
2 stops
Depart: Mon Aug 28 2017 Return: Wed Aug 30 2017 Trip spans 3 days
Multiple Airlines
Multiple Airlines
SJU
12:00a
MDW
6:09p
18h 09m
2 stops
MDW
12:00a
SJU
4:31p
16h 31m
2 stops
Depart: Sat Oct 7 2017 Return: Wed Oct 11 2017 Trip spans 5 days
Delta
Delta
SJU
12:00a
MDW
9:19a
9h 19m
1 stop
MDW
12:00a
SJU
1:40p
13h 40m
2 stops
Depart: Sat Sep 16 2017 Return: Fri Sep 29 2017 Trip spans 14 days
Delta
Delta
SJU
12:00a
MDW
7:15a
7h 15m
1 stop
MDW
12:00a
SJU
8:50a
8h 50m
1 stop
Depart: Tue Oct 3 2017 Return: Mon Oct 9 2017 Trip spans 7 days
Delta
Delta
SJU
12:00a
MDW
9:36a
9h 36m
1 stop
MDW
12:00a
SJU
6:24a
6h 24m
1 stop
Depart: Fri Oct 13 2017 Return: Wed Oct 18 2017 Trip spans 6 days
Multiple Airlines
Multiple Airlines
SJU
12:00a
MDW
8:27a
32h 27m
2 stops
MDW
12:00a
SJU
3:21a
27h 21m
1 stop
Depart: Thu Oct 5 2017 Return: Sun Oct 8 2017 Trip spans 4 days
Delta
Delta
SJU
12:00a
MDW
9:36a
9h 36m
1 stop
MDW
12:00a
SJU
6:11a
6h 11m
1 stop
Depart: Sat Oct 7 2017 Return: Tue Oct 10 2017 Trip spans 4 days
Delta
Delta
SJU
12:00a
MDW
9:19a
9h 19m
1 stop
MDW
12:00a
SJU
6:11a
6h 11m
1 stop
Depart: Mon Aug 21 2017 Return: Wed Aug 23 2017 Trip spans 3 days
Multiple Airlines
Multiple Airlines
SJU
12:00a
MDW
5:59p
17h 59m
2 stops
MDW
12:00a
SJU
10:55a
10h 55m
2 stops
Depart: Thu Oct 12 2017 Return: Thu Oct 19 2017 Trip spans 8 days
Delta
Delta
SJU
12:00a
MDW
7:15a
7h 15m
1 stop
MDW
12:00a
SJU
8:36a
8h 36m
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.

We compile tonnes of data for you
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

San Juan
$389
Destination

Chicago
$389
Airlines