Find Deals on 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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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Puerto Rico to Chicago Midway

(Round-trip)
Depart: Thu Apr 20 2017 Return: Mon Apr 24 2017 Trip spans 5 days
Delta
Delta
SJU
10:16a
MDW
7:25p
9h 09m
1 stop
MDW
3:20a
SJU
5:23p
14h 03m
2 stops
Depart: Wed May 10 2017 Return: Wed May 17 2017 Trip spans 8 days
Delta
Delta
SJU
3:15a
MDW
10:33a
7h 18m
1 stop
MDW
10:10a
SJU
4:46p
6h 36m
1 stop
Depart: Thu May 11 2017 Return: Mon May 15 2017 Trip spans 5 days
Delta
Delta
SJU
10:20a
MDW
7:20p
9h 00m
1 stop
MDW
10:10a
SJU
4:46p
6h 36m
1 stop
Depart: Thu Apr 27 2017 Return: Sun Apr 30 2017 Trip spans 4 days
Delta
Delta
SJU
10:16a
MDW
5:20p
7h 04m
1 stop
MDW
8:24a
SJU
4:33p
8h 09m
1 stop
Depart: Fri Apr 28 2017 Return: Wed May 3 2017 Trip spans 6 days
Delta
Delta
SJU
11:45a
MDW
7:25p
7h 40m
1 stop
MDW
2:00a
SJU
8:25a
6h 25m
1 stop
Depart: Fri May 5 2017 Return: Tue May 9 2017 Trip spans 5 days
Delta
Delta
SJU
10:20a
MDW
7:20p
9h 00m
1 stop
MDW
10:10a
SJU
4:46p
6h 36m
1 stop
Depart: Tue May 9 2017 Return: Sun May 14 2017 Trip spans 6 days
Delta
Delta
SJU
3:15a
MDW
10:33a
7h 18m
1 stop
MDW
10:10a
SJU
4:46p
6h 36m
1 stop
Depart: Fri May 12 2017 Return: Mon May 15 2017 Trip spans 4 days
Delta
Delta
SJU
10:20a
MDW
7:20p
9h 00m
1 stop
MDW
2:00a
SJU
8:25a
6h 25m
1 stop
Depart: Thu Sep 28 2017 Return: Sun Oct 1 2017 Trip spans 4 days
Delta
Delta
SJU
8:51a
MDW
5:43p
8h 52m
1 stop
MDW
9:40a
SJU
4:34p
6h 54m
1 stop
Depart: Wed May 17 2017 Return: Tue May 30 2017 Trip spans 14 days
Delta
Delta
SJU
10:20a
MDW
7:20p
9h 00m
1 stop
MDW
2:00a
SJU
8:25a
6h 25m
1 stop
Depart: Fri Apr 21 2017 Return: Mon Apr 24 2017 Trip spans 4 days
Delta
Delta
SJU
10:16a
MDW
7:25p
9h 09m
1 stop
MDW
3:20a
SJU
5:23p
14h 03m
2 stops
Depart: Tue Sep 5 2017 Return: Sat Sep 9 2017 Trip spans 5 days
Delta
Delta
SJU
11:50a
MDW
7:48p
7h 58m
1 stop
MDW
1:44a
SJU
10:23a
8h 39m
2 stops
Depart: Wed Apr 26 2017 Return: Fri Apr 28 2017 Trip spans 3 days
Delta
Delta
SJU
10:16a
MDW
7:25p
9h 09m
1 stop
MDW
10:08a
SJU
4:33p
6h 25m
1 stop
Depart: Tue May 2 2017 Return: Tue May 16 2017 Trip spans 15 days
Delta
Delta
SJU
11:42a
MDW
7:20p
7h 38m
1 stop
MDW
2:00a
SJU
8:25a
6h 25m
1 stop
Depart: Tue May 23 2017 Return: Tue May 30 2017 Trip spans 8 days
Delta
Delta
SJU
8:45a
MDW
3:45p
7h 00m
1 stop
MDW
2:00a
SJU
8:25a
6h 25m
1 stop
Depart: Wed Aug 2 2017 Return: Mon Aug 7 2017 Trip spans 6 days
Delta
Delta
SJU
3:25a
MDW
10:07a
6h 42m
1 stop
MDW
9:40a
SJU
4:34p
6h 54m
1 stop
Depart: Wed Aug 16 2017 Return: Mon Aug 21 2017 Trip spans 6 days
Delta
Delta
SJU
10:14a
MDW
5:43p
7h 29m
1 stop
MDW
9:40a
SJU
4:34p
6h 54m
1 stop
Depart: Thu May 18 2017 Return: Sun May 21 2017 Trip spans 4 days
Delta
Delta
SJU
3:15a
MDW
10:33a
7h 18m
1 stop
MDW
2:00a
SJU
8:25a
6h 25m
1 stop
Depart: Wed Jun 7 2017 Return: Tue Aug 1 2017 Trip spans 56 days
Delta
Delta
SJU
3:15a
MDW
10:33a
7h 18m
1 stop
MDW
9:40a
SJU
4:34p
6h 54m
1 stop
Depart: Mon May 8 2017 Return: Wed May 17 2017 Trip spans 10 days
Delta
Delta
SJU
3:15a
MDW
10:33a
7h 18m
1 stop
MDW
8:05a
SJU
4:46p
8h 41m
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