Find Cheap 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: Wed Oct 4 2017 Return: Tue Oct 10 2017 Trip spans 7 days
Delta
Delta
SJU
11:50a
MDW
8:07p
8h 17m
1 stop
MDW
10:10a
SJU
4:34p
6h 24m
1 stop
Depart: Thu Oct 5 2017 Return: Tue Oct 10 2017 Trip spans 6 days
Delta
Delta
SJU
11:50a
MDW
8:07p
8h 17m
1 stop
MDW
2:00a
SJU
8:22a
6h 22m
1 stop
Depart: Thu Oct 19 2017 Return: Mon Oct 23 2017 Trip spans 5 days
Delta
Delta
SJU
3:25a
MDW
10:37a
7h 12m
1 stop
MDW
10:10a
SJU
4:34p
6h 24m
1 stop
Depart: Sat Oct 7 2017 Return: Tue Oct 10 2017 Trip spans 4 days
Delta
Delta
SJU
3:00a
MDW
5:11p
14h 11m
2 stops
MDW
8:00a
SJU
4:34p
8h 34m
1 stop
Depart: Tue Sep 12 2017 Return: Fri Sep 15 2017 Trip spans 4 days
Delta
Delta
SJU
10:14a
MDW
8:02p
9h 48m
1 stop
MDW
3:20a
SJU
9:52a
6h 32m
1 stop
Depart: Fri Sep 15 2017 Return: Mon Sep 18 2017 Trip spans 4 days
Delta
Delta
SJU
10:14a
MDW
8:07p
9h 53m
1 stop
MDW
3:20a
SJU
9:52a
6h 32m
1 stop
Depart: Thu Sep 21 2017 Return: Sun Sep 24 2017 Trip spans 4 days
Delta
Delta
SJU
3:25a
MDW
10:37a
7h 12m
1 stop
MDW
2:00a
SJU
8:22a
6h 22m
1 stop
Depart: Thu Sep 28 2017 Return: Sun Oct 1 2017 Trip spans 4 days
Delta
Delta
SJU
10:14a
MDW
8:07p
9h 53m
1 stop
MDW
8:00a
SJU
4:34p
8h 34m
1 stop
Depart: Fri Oct 20 2017 Return: Tue Oct 24 2017 Trip spans 5 days
Delta
Delta
SJU
11:50a
MDW
8:07p
8h 17m
1 stop
MDW
3:20a
SJU
9:52a
6h 32m
1 stop
Depart: Thu Oct 26 2017 Return: Sun Oct 29 2017 Trip spans 4 days
Delta
Delta
SJU
3:25a
MDW
12:46p
9h 21m
1 stop
MDW
3:20a
SJU
9:52a
6h 32m
1 stop
Depart: Tue Aug 8 2017 Return: Tue Aug 15 2017 Trip spans 8 days
Delta
Delta
SJU
11:25a
MDW
7:55p
8h 30m
1 stop
MDW
3:20a
SJU
9:52a
6h 32m
1 stop
Depart: Fri Nov 10 2017 Return: Mon Nov 13 2017 Trip spans 4 days
Delta
Delta
SJU
11:50a
MDW
7:53p
8h 03m
1 stop
MDW
1:00a
SJU
7:22a
6h 22m
1 stop
Depart: Thu Aug 10 2017 Return: Sat Aug 12 2017 Trip spans 3 days
Delta
Delta
SJU
10:19a
MDW
7:55p
9h 36m
1 stop
MDW
3:20a
SJU
10:49a
7h 29m
1 stop
Depart: Tue Aug 15 2017 Return: Tue Aug 22 2017 Trip spans 8 days
Delta
Delta
SJU
8:51a
MDW
5:43p
8h 52m
1 stop
MDW
9:40a
SJU
4:34p
6h 54m
1 stop
Depart: Sat Sep 30 2017 Return: Sat Oct 7 2017 Trip spans 8 days
Delta
Delta
SJU
11:50a
MDW
8:05p
8h 15m
1 stop
MDW
8:00a
SJU
4:34p
8h 34m
1 stop
Depart: Tue Jul 18 2017 Return: Wed Aug 2 2017 Trip spans 16 days
Delta
Delta
SJU
10:19a
MDW
7:55p
9h 36m
1 stop
MDW
2:55a
SJU
5:09p
14h 14m
2 stops
Depart: Tue Oct 3 2017 Return: Mon Oct 9 2017 Trip spans 7 days
Delta
Delta
SJU
3:25a
MDW
10:37a
7h 12m
1 stop
MDW
2:00a
SJU
9:52a
7h 52m
1 stop
Depart: Fri Oct 6 2017 Return: Tue Oct 10 2017 Trip spans 5 days
Delta
Delta
SJU
10:14a
MDW
6:03p
7h 49m
1 stop
MDW
2:00a
SJU
9:52a
7h 52m
1 stop
Depart: Sat Oct 21 2017 Return: Wed Oct 25 2017 Trip spans 5 days
Delta
Delta
SJU
10:14a
MDW
8:05p
9h 51m
1 stop
MDW
3:20a
SJU
9:52a
6h 32m
1 stop
Depart: Wed Jun 14 2017 Return: Wed Jun 21 2017 Trip spans 8 days
Delta
Delta
SJU
10:21a
MDW
8:02p
9h 41m
1 stop
MDW
2:00a
SJU
9:34a
7h 34m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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