Find Deals on Flights from San Juan 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 San Juan 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: Tue Jul 18 2017 Return: Tue Aug 1 2017 Trip spans 15 days
Southwest
Southwest
SJU
2:00p
MDW
8:40p
6h 40m
1 stop
MDW
3:05a
SJU
10:55a
7h 50m
1 stop
Depart: Thu May 4 2017 Return: Mon May 8 2017 Trip spans 5 days
Delta
Delta
SJU
10:20a
MDW
7:20p
9h 00m
1 stop
MDW
8:05a
SJU
4:46p
8h 41m
1 stop
Depart: Tue May 9 2017 Return: Mon May 15 2017 Trip spans 7 days
Delta
Delta
SJU
11:42a
MDW
7:20p
7h 38m
1 stop
MDW
10:10a
SJU
4:46p
6h 36m
1 stop
Depart: Wed May 10 2017 Return: Mon May 15 2017 Trip spans 6 days
Delta
Delta
SJU
3:15a
MDW
12:20p
9h 05m
1 stop
MDW
10:10a
SJU
4:46p
6h 36m
1 stop
Depart: Sat Sep 30 2017 Return: Wed Oct 4 2017 Trip spans 5 days
Delta
Delta
SJU
10:14a
MDW
5:41p
7h 27m
1 stop
MDW
3:20a
SJU
5:13p
13h 53m
2 stops
Depart: Thu Apr 27 2017 Return: Sun Apr 30 2017 Trip spans 4 days
Delta
Delta
SJU
11:45a
MDW
7:25p
7h 40m
1 stop
MDW
2:00a
SJU
8:21a
6h 21m
1 stop
Depart: Fri May 5 2017 Return: Mon May 8 2017 Trip spans 4 days
Delta
Delta
SJU
10:20a
MDW
7:20p
9h 00m
1 stop
MDW
2:00a
SJU
9:47a
7h 47m
1 stop
Depart: Thu May 11 2017 Return: Sun May 14 2017 Trip spans 4 days
Delta
Delta
SJU
11:42a
MDW
7:20p
7h 38m
1 stop
MDW
2:00a
SJU
8:25a
6h 25m
1 stop
Depart: Fri Apr 28 2017 Return: Sun Apr 30 2017 Trip spans 3 days
Delta
Delta
SJU
3:15a
MDW
10:33a
7h 18m
1 stop
MDW
2:00a
SJU
8:21a
6h 21m
1 stop
Depart: Fri Apr 21 2017 Return: Tue Apr 25 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: 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: Thu May 18 2017 Return: Mon May 22 2017 Trip spans 5 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 Aug 2 2017 Return: Wed Aug 16 2017 Trip spans 15 days
Delta
Delta
SJU
3:25a
MDW
10:07a
6h 42m
1 stop
MDW
8:00a
SJU
4:34p
8h 34m
1 stop
Depart: Tue May 23 2017 Return: Tue May 30 2017 Trip spans 8 days
Delta
Delta
SJU
8:45a
MDW
5:00p
8h 15m
1 stop
MDW
2:00a
SJU
8:25a
6h 25m
1 stop
Depart: Wed May 3 2017 Return: Thu May 18 2017 Trip spans 16 days
Delta
Delta
SJU
3:15a
MDW
10:33a
7h 18m
1 stop
MDW
8:05a
SJU
4:46p
8h 41m
1 stop
Depart: Fri May 19 2017 Return: Mon May 22 2017 Trip spans 4 days
Delta
Delta
SJU
11:42a
MDW
7:20p
7h 38m
1 stop
MDW
2:00a
SJU
8:25a
6h 25m
1 stop
Depart: Wed Aug 16 2017 Return: Mon Aug 21 2017 Trip spans 6 days
Delta
Delta
SJU
8:51a
MDW
5:43p
8h 52m
1 stop
MDW
8:00a
SJU
4:34p
8h 34m
1 stop
Depart: Tue Aug 1 2017 Return: Mon Aug 7 2017 Trip spans 7 days
Delta
Delta
SJU
8:51a
MDW
5:43p
8h 52m
1 stop
MDW
9:40a
SJU
4:34p
6h 54m
1 stop
Depart: Tue Jun 6 2017 Return: Tue Jun 13 2017 Trip spans 8 days
Delta
Delta
SJU
10:20a
MDW
7:20p
9h 00m
1 stop
MDW
9:40a
SJU
4:34p
6h 54m
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,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

San Juan
$389
Destination

Chicago
$389