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
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 Puerto Rico to Chicago Midway

(Round-trip)
Depart: Fri Feb 10 2017 Return: Sun Feb 12 2017 Trip spans 3 days
Delta
Delta
SJU
3:15a
MDW
12:03p
8h 48m
1 stop
MDW
9:08a
SJU
3:37p
6h 29m
1 stop
Depart: Tue Feb 14 2017 Return: Tue Feb 21 2017 Trip spans 8 days
Delta
Delta
SJU
11:45a
MDW
7:46p
8h 01m
1 stop
MDW
9:11a
SJU
3:33p
6h 22m
1 stop
Depart: Thu Feb 16 2017 Return: Tue Feb 21 2017 Trip spans 6 days
Delta
Delta
SJU
8:55a
MDW
5:02p
8h 07m
1 stop
MDW
7:25a
SJU
3:33p
8h 08m
1 stop
Depart: Wed Feb 22 2017 Return: Sun Feb 26 2017 Trip spans 5 days
Delta
Delta
SJU
3:15a
MDW
10:34a
7h 19m
1 stop
MDW
7:25a
SJU
3:33p
8h 08m
1 stop
Depart: Wed Mar 1 2017 Return: Mon Mar 6 2017 Trip spans 6 days
Delta
Delta
SJU
3:15a
MDW
10:34a
7h 19m
1 stop
MDW
7:25a
SJU
3:33p
8h 08m
1 stop
Depart: Fri Mar 3 2017 Return: Mon Mar 6 2017 Trip spans 4 days
Delta
Delta
SJU
3:15a
MDW
12:05p
8h 50m
1 stop
MDW
7:25a
SJU
3:33p
8h 08m
1 stop
Depart: Tue Mar 14 2017 Return: Wed Mar 22 2017 Trip spans 9 days
Delta
Delta
SJU
10:15a
MDW
7:10p
8h 55m
1 stop
MDW
2:30a
SJU
10:05a
7h 35m
1 stop
Depart: Wed Mar 15 2017 Return: Mon Mar 27 2017 Trip spans 13 days
Delta
Delta
SJU
3:05a
MDW
12:12p
9h 07m
1 stop
MDW
9:48a
SJU
4:39p
6h 51m
1 stop
Depart: Wed Mar 22 2017 Return: Mon Mar 27 2017 Trip spans 6 days
Delta
Delta
SJU
10:15a
MDW
7:10p
8h 55m
1 stop
MDW
9:48a
SJU
4:39p
6h 51m
1 stop
Depart: Wed Apr 5 2017 Return: Wed Apr 12 2017 Trip spans 8 days
Delta
Delta
SJU
8:51a
MDW
5:02p
8h 11m
1 stop
MDW
2:00a
SJU
8:22a
6h 22m
1 stop
Depart: Sat Feb 11 2017 Return: Mon Feb 13 2017 Trip spans 3 days
Delta
Delta
SJU
3:00a
MDW
7:07p
16h 07m
2 stops
MDW
9:08a
SJU
3:37p
6h 29m
1 stop
Depart: Fri Feb 3 2017 Return: Sun Feb 12 2017 Trip spans 10 days
Delta
Delta
SJU
10:21a
MDW
7:46p
9h 25m
1 stop
MDW
9:08a
SJU
3:37p
6h 29m
1 stop
Depart: Sat Feb 4 2017 Return: Sun Feb 12 2017 Trip spans 9 days
Delta
Delta
SJU
11:45a
MDW
7:07p
7h 22m
1 stop
MDW
7:20a
SJU
3:37p
8h 17m
1 stop
Depart: Tue Feb 7 2017 Return: Sun Feb 12 2017 Trip spans 6 days
Delta
Delta
SJU
8:55a
MDW
5:02p
8h 07m
1 stop
MDW
9:08a
SJU
3:37p
6h 29m
1 stop
Depart: Wed Feb 8 2017 Return: Sun Feb 12 2017 Trip spans 5 days
Delta
Delta
SJU
10:21a
MDW
7:46p
9h 25m
1 stop
MDW
7:20a
SJU
3:37p
8h 17m
1 stop
Depart: Thu Feb 9 2017 Return: Sun Feb 12 2017 Trip spans 4 days
Delta
Delta
SJU
11:45a
MDW
7:46p
8h 01m
1 stop
MDW
9:08a
SJU
3:37p
6h 29m
1 stop
Depart: Wed Feb 15 2017 Return: Tue Feb 21 2017 Trip spans 7 days
Delta
Delta
SJU
2:40a
MDW
6:00p
15h 20m
2 stops
MDW
7:25a
SJU
3:33p
8h 08m
1 stop
Depart: Mon Feb 13 2017 Return: Tue Feb 21 2017 Trip spans 9 days
Delta
Delta
SJU
11:45a
MDW
7:46p
8h 01m
1 stop
MDW
1:00a
SJU
9:04a
8h 04m
1 stop
Depart: Thu Feb 23 2017 Return: Sun Feb 26 2017 Trip spans 4 days
Delta
Delta
SJU
3:15a
MDW
10:34a
7h 19m
1 stop
MDW
7:25a
SJU
3:33p
8h 08m
1 stop
Depart: Tue Apr 4 2017 Return: Wed Apr 12 2017 Trip spans 9 days
Delta
Delta
SJU
8:51a
MDW
5:02p
8h 11m
1 stop
MDW
2:00a
SJU
9:52a
7h 52m
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
$308
Destination

Chicago
$308
Airlines