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: Wed Nov 29 2017 Return: Mon Dec 4 2017 Trip spans 6 days
Delta
Delta
SJU
12:00a
MDW
6:45a
6h 45m
1 stop
MDW
12:00a
SJU
6:34a
6h 34m
1 stop
Depart: Tue Dec 5 2017 Return: Thu Dec 7 2017 Trip spans 3 days
Delta
Delta
SJU
12:00a
MDW
6:45a
6h 45m
1 stop
MDW
12:00a
SJU
7:50a
7h 50m
1 stop
Depart: Sun Dec 3 2017 Return: Thu Dec 7 2017 Trip spans 5 days
Delta
Delta
SJU
12:00a
MDW
6:45a
6h 45m
1 stop
MDW
12:00a
SJU
7:50a
7h 50m
1 stop
Depart: Thu Dec 7 2017 Return: Sun Dec 10 2017 Trip spans 4 days
Delta
Delta
SJU
12:00a
MDW
6:45a
6h 45m
1 stop
MDW
12:00a
SJU
7:50a
7h 50m
1 stop
Depart: Fri Jan 12 2018 Return: Tue Jan 16 2018 Trip spans 5 days
Delta
Delta
SJU
12:00a
MDW
7:53a
7h 53m
1 stop
MDW
12:00a
SJU
7:52a
7h 52m
1 stop
Depart: Fri Nov 10 2017 Return: Fri Nov 24 2017 Trip spans 15 days
Delta
Delta
SJU
12:00a
MDW
8:05a
8h 05m
1 stop
MDW
12:00a
SJU
7:49a
7h 49m
1 stop
Depart: Fri Dec 1 2017 Return: Sun Dec 10 2017 Trip spans 10 days
Delta
Delta
SJU
12:00a
MDW
6:45a
6h 45m
1 stop
MDW
12:00a
SJU
7:50a
7h 50m
1 stop
Depart: Sat Apr 21 2018 Return: Thu Apr 26 2018 Trip spans 6 days
Delta
Delta
SJU
12:00a
MDW
9:57a
9h 57m
2 stops
MDW
12:00a
SJU
6:22a
6h 22m
1 stop
Depart: Fri Nov 17 2017 Return: Mon Nov 20 2017 Trip spans 4 days
Delta
Delta
SJU
12:00a
MDW
8:05a
8h 05m
1 stop
MDW
12:00a
SJU
7:53a
7h 53m
1 stop
Depart: Sat Dec 23 2017 Return: Fri Jan 5 2018 Trip spans 14 days
Delta
Delta
SJU
12:00a
MDW
7:23a
7h 23m
1 stop
MDW
12:00a
SJU
7:52a
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.

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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

San Juan
$382
Destination

Chicago
$382
Airlines