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 Oct 11 2017 Return: Wed Nov 1 2017 Trip spans 22 days
Delta
Delta
SJU
12:00a
MDW
7:12a
7h 12m
1 stop
MDW
12:00a
SJU
1:53p
13h 53m
2 stops
Depart: Tue Jul 11 2017 Return: Mon Jul 17 2017 Trip spans 7 days
Southwest
Southwest
SJU
12:00a
MDW
7:30a
7h 30m
1 stop
MDW
12:00a
SJU
6:15a
6h 15m
1 stop
Depart: Mon Jul 17 2017 Return: Tue Jul 25 2017 Trip spans 9 days
Multiple Airlines
Multiple Airlines
SJU
12:00a
MDW
8:08p
20h 08m
2 stops
MDW
12:00a
SJU
4:11p
16h 11m
3 stops
Depart: Thu Oct 19 2017 Return: Tue Oct 24 2017 Trip spans 6 days
Delta
Delta
SJU
12:00a
MDW
7:49a
7h 49m
1 stop
MDW
12:00a
SJU
1:53p
13h 53m
2 stops
Depart: Fri Oct 20 2017 Return: Tue Oct 24 2017 Trip spans 5 days
Delta
Delta
SJU
12:00a
MDW
8:17a
8h 17m
1 stop
MDW
12:00a
SJU
3:13p
15h 13m
2 stops
Depart: Thu Oct 19 2017 Return: Mon Oct 23 2017 Trip spans 5 days
Delta
Delta
SJU
12:00a
MDW
8:17a
8h 17m
1 stop
MDW
12:00a
SJU
6:24a
6h 24m
1 stop
Depart: Thu Oct 26 2017 Return: Sun Oct 29 2017 Trip spans 4 days
Delta
Delta
SJU
12:00a
MDW
9:21a
9h 21m
1 stop
MDW
12:00a
SJU
6:32a
6h 32m
1 stop
Depart: Tue Aug 1 2017 Return: Wed Aug 9 2017 Trip spans 9 days
Delta
Delta
SJU
12:00a
MDW
7:11a
7h 11m
1 stop
MDW
12:00a
SJU
9:05a
9h 05m
1 stop
Depart: Mon Sep 18 2017 Return: Mon Sep 25 2017 Trip spans 8 days
Delta
Delta
SJU
12:00a
MDW
8:17a
8h 17m
1 stop
MDW
12:00a
SJU
6:22a
6h 22m
1 stop
Depart: Fri Oct 6 2017 Return: Wed Oct 11 2017 Trip spans 6 days
Delta
Delta
SJU
12:00a
MDW
7:12a
7h 12m
1 stop
MDW
12:00a
SJU
8:34a
8h 34m
1 stop
Depart: Tue Oct 3 2017 Return: Mon Oct 9 2017 Trip spans 7 days
Delta
Delta
SJU
12:00a
MDW
10:32a
10h 32m
2 stops
MDW
12:00a
SJU
6:22a
6h 22m
1 stop
Depart: Sat Aug 12 2017 Return: Mon Aug 21 2017 Trip spans 10 days
Delta
Delta
SJU
12:00a
MDW
8:45a
8h 45m
1 stop
MDW
12:00a
SJU
7:47a
7h 47m
1 stop
Depart: Mon Aug 14 2017 Return: Mon Aug 21 2017 Trip spans 8 days
Delta
Delta
SJU
12:00a
MDW
7:01a
7h 01m
1 stop
MDW
12:00a
SJU
6:27a
6h 27m
1 stop
Depart: Wed Aug 16 2017 Return: Sun Aug 20 2017 Trip spans 5 days
Delta
Delta
SJU
12:00a
MDW
7:58a
7h 58m
1 stop
MDW
12:00a
SJU
7:47a
7h 47m
1 stop
Depart: Tue Oct 17 2017 Return: Tue Oct 24 2017 Trip spans 8 days
Delta
Delta
SJU
12:00a
MDW
7:12a
7h 12m
1 stop
MDW
12:00a
SJU
6:32a
6h 32m
1 stop
Depart: Wed Oct 18 2017 Return: Tue Oct 24 2017 Trip spans 7 days
Delta
Delta
SJU
12:00a
MDW
9:21a
9h 21m
1 stop
MDW
12:00a
SJU
6:22a
6h 22m
1 stop
Depart: Thu Aug 17 2017 Return: Sun Aug 20 2017 Trip spans 4 days
Delta
Delta
SJU
12:00a
MDW
9:15a
9h 15m
1 stop
MDW
12:00a
SJU
7:47a
7h 47m
1 stop
Depart: Mon Jun 26 2017 Return: Sat Aug 19 2017 Trip spans 55 days
Delta
Delta
SJU
12:00a
MDW
9:06a
9h 06m
1 stop
MDW
12:00a
SJU
6:26a
6h 26m
1 stop
Depart: Tue Jul 4 2017 Return: Tue Aug 8 2017 Trip spans 36 days
Delta
Delta
SJU
12:00a
MDW
9:32a
9h 32m
1 stop
MDW
12:00a
SJU
9:05a
9h 05m
1 stop
Depart: Wed Aug 16 2017 Return: Sat Aug 19 2017 Trip spans 4 days
Delta
Delta
SJU
12:00a
MDW
7:58a
7h 58m
1 stop
MDW
12:00a
SJU
8:39a
8h 39m
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
$387
Destination

Chicago
$387