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 18 2017 Return: Tue Oct 24 2017 Trip spans 7 days
Delta
Delta
SJU
9:30a
MDW
8:07p
10h 37m
2 stops
MDW
3:20a
SJU
5:13p
13h 53m
2 stops
Depart: Thu Oct 5 2017 Return: Tue Oct 10 2017 Trip spans 6 days
Delta
Delta
SJU
10:14a
MDW
8:07p
9h 53m
1 stop
MDW
3:20a
SJU
5:13p
13h 53m
2 stops
Depart: Tue Oct 17 2017 Return: Tue Oct 24 2017 Trip spans 8 days
Delta
Delta
SJU
11:50a
MDW
8:02p
8h 12m
1 stop
MDW
3:20a
SJU
5:13p
13h 53m
2 stops
Depart: Thu Oct 19 2017 Return: Tue Oct 24 2017 Trip spans 6 days
Delta
Delta
SJU
3:25a
MDW
12:46p
9h 21m
1 stop
MDW
2:00a
SJU
5:13p
15h 13m
2 stops
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
5:13p
13h 53m
2 stops
Depart: Thu Oct 26 2017 Return: Sun Oct 29 2017 Trip spans 4 days
Delta
Delta
SJU
9:30a
MDW
8:07p
10h 37m
2 stops
MDW
2:00a
SJU
9:52a
7h 52m
1 stop
Depart: Wed Nov 1 2017 Return: Wed Nov 8 2017 Trip spans 8 days
Delta
Delta
SJU
3:00a
MDW
6:43p
15h 43m
2 stops
MDW
2:20a
SJU
4:24p
14h 04m
2 stops
Depart: Fri Dec 1 2017 Return: Mon Dec 4 2017 Trip spans 4 days
Delta
Delta
SJU
3:00a
MDW
7:15p
16h 15m
2 stops
MDW
8:40a
SJU
3:34p
6h 54m
1 stop
Depart: Thu Sep 14 2017 Return: Mon Sep 18 2017 Trip spans 5 days
Delta
Delta
SJU
11:30a
MDW
7:55p
8h 25m
1 stop
MDW
10:06a
SJU
4:50p
6h 44m
1 stop
Depart: Tue Sep 19 2017 Return: Mon Sep 25 2017 Trip spans 7 days
Delta
Delta
SJU
10:20a
MDW
7:55p
9h 35m
1 stop
MDW
2:00a
SJU
8:23a
6h 23m
1 stop
Depart: Thu Sep 28 2017 Return: Tue Oct 3 2017 Trip spans 6 days
Delta
Delta
SJU
10:20a
MDW
5:51p
7h 31m
1 stop
MDW
3:20a
SJU
9:52a
6h 32m
1 stop
Depart: Wed Oct 11 2017 Return: Mon Oct 16 2017 Trip spans 6 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 12 2017 Return: Mon Oct 16 2017 Trip spans 5 days
Delta
Delta
SJU
10:14a
MDW
8:07p
9h 53m
1 stop
MDW
3:20a
SJU
9:52a
6h 32m
1 stop
Depart: Wed Jan 17 2018 Return: Wed Jan 24 2018 Trip spans 8 days
Delta
Delta
SJU
10:15a
MDW
6:38p
8h 23m
1 stop
MDW
4:18a
SJU
4:24p
12h 06m
2 stops
Depart: Thu Sep 21 2017 Return: Sun Sep 24 2017 Trip spans 4 days
Delta
Delta
SJU
3:15a
MDW
12:40p
9h 25m
1 stop
MDW
2:00a
SJU
8:23a
6h 23m
1 stop
Depart: Fri Sep 29 2017 Return: Mon Oct 2 2017 Trip spans 4 days
Delta
Delta
SJU
3:15a
MDW
12:40p
9h 25m
1 stop
MDW
2:00a
SJU
8:22a
6h 22m
1 stop
Depart: Wed Aug 30 2017 Return: Tue Sep 5 2017 Trip spans 7 days
Delta
Delta
SJU
10:20a
MDW
7:55p
9h 35m
1 stop
MDW
3:25a
SJU
9:35a
6h 10m
1 stop
Depart: Fri Nov 3 2017 Return: Sun Nov 5 2017 Trip spans 3 days
Delta
Delta
SJU
3:25a
MDW
10:07a
6h 42m
1 stop
MDW
2:20a
SJU
8:52a
6h 32m
1 stop
Depart: Wed Dec 20 2017 Return: Mon Jan 8 2018 Trip spans 20 days
Delta
Delta
SJU
11:50a
MDW
7:53p
8h 03m
1 stop
MDW
1:00a
SJU
8:52a
7h 52m
1 stop
Depart: Sat Oct 21 2017 Return: Tue Oct 24 2017 Trip spans 4 days
Delta
Delta
SJU
8:51a
MDW
4:16p
7h 25m
1 stop
MDW
2:00a
SJU
5:13p
15h 13m
2 stops
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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Airports
Origin

San Juan
$357
Destination

Chicago
$357
Airlines