Find Cheap Flights from Chicago Midway to Jamaica

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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago Midway to Jamaica

(Round-trip)
Depart: Mon Oct 30 2017 Return: Fri Nov 3 2017 Trip spans 5 days
Delta
Delta
MDW
12:00a
MBJ
8:00a
8h 00m
1 stop
MBJ
12:00a
MDW
12:35p
12h 35m
1 stop
Depart: Sat Dec 2 2017 Return: Wed Dec 6 2017 Trip spans 5 days
Delta
Delta
MDW
12:00a
MBJ
4:20p
16h 20m
1 stop
MBJ
12:00a
MDW
6:30a
6h 30m
1 stop
Depart: Sat Dec 9 2017 Return: Sat Dec 16 2017 Trip spans 8 days
Delta
Delta
MDW
12:00a
MBJ
4:20p
16h 20m
1 stop
MBJ
12:00a
MDW
9:50a
9h 50m
1 stop
Depart: Sat Jan 6 2018 Return: Sat Jan 13 2018 Trip spans 8 days
Delta
Delta
MDW
12:00a
MBJ
5:55a
5h 55m
1 stop
MBJ
12:00a
MDW
9:12a
9h 12m
1 stop
Depart: Tue Jan 9 2018 Return: Tue Jan 16 2018 Trip spans 8 days
Delta
Delta
MDW
12:00a
MBJ
7:58a
7h 58m
1 stop
MBJ
12:00a
MDW
7:10a
7h 10m
1 stop
Depart: Sat Feb 3 2018 Return: Tue Feb 6 2018 Trip spans 4 days
Delta
Delta
MDW
12:00a
MBJ
1:40p
13h 40m
1 stop
MBJ
12:00a
MDW
9:08a
9h 08m
1 stop
Depart: Wed Feb 7 2018 Return: Wed Feb 14 2018 Trip spans 8 days
Delta
Delta
MDW
12:00a
MBJ
7:58a
7h 58m
1 stop
MBJ
12:00a
MDW
7:10a
7h 10m
1 stop
Depart: Sat Nov 25 2017 Return: Wed Nov 29 2017 Trip spans 5 days
Delta
Delta
MDW
12:00a
MBJ
3:55p
15h 55m
2 stops
MBJ
12:00a
MDW
9:53a
9h 53m
2 stops
Depart: Mon Nov 6 2017 Return: Thu Nov 9 2017 Trip spans 4 days
Delta
Delta
MDW
12:00a
MBJ
6:40a
6h 40m
1 stop
MBJ
12:00a
MDW
11:10a
11h 10m
1 stop
Depart: Fri Mar 9 2018 Return: Wed Mar 14 2018 Trip spans 5 days
Delta
Delta
MDW
12:00a
MBJ
12:20p
12h 20m
1 stop
MBJ
12:00a
MDW
2:38p
14h 38m
1 stop
Depart: Fri Jan 26 2018 Return: Sun Jan 28 2018 Trip spans 3 days
Delta
Delta
MDW
12:00a
KIN
12:16p
12h 16m
1 stop
KIN
12:00a
MDW
9:27a
9h 27m
1 stop
Depart: Mon Mar 12 2018 Return: Mon Mar 19 2018 Trip spans 8 days
Delta
Delta
MDW
12:00a
KIN
8:06a
8h 06m
1 stop
KIN
12:00a
MDW
1:53p
13h 53m
1 stop
Depart: Fri Oct 27 2017 Return: Wed Nov 1 2017 Trip spans 6 days
Delta
Delta
MDW
12:00a
MBJ
8:00a
8h 00m
1 stop
MBJ
12:00a
MDW
10:59a
10h 59m
1 stop
Depart: Thu Dec 7 2017 Return: Thu Dec 14 2017 Trip spans 8 days
Delta
Delta
MDW
12:00a
MBJ
5:40a
5h 40m
1 stop
MBJ
12:00a
MDW
1:15p
13h 15m
1 stop
Depart: Sun Oct 29 2017 Return: Sun Nov 5 2017 Trip spans 8 days
Delta
Delta
MDW
12:00a
MBJ
1:55p
13h 55m
1 stop
MBJ
12:00a
MDW
1:40p
14h 40m
1 stop
Depart: Tue Nov 28 2017 Return: Mon Dec 4 2017 Trip spans 7 days
Delta
Delta
MDW
12:00a
MBJ
7:58a
7h 58m
1 stop
MBJ
12:00a
MDW
9:51a
9h 51m
1 stop
Depart: Thu Oct 19 2017 Return: Tue Oct 24 2017 Trip spans 6 days
Delta
Delta
MDW
12:00a
KIN
12:30p
12h 30m
1 stop
KIN
12:00a
MDW
11:35a
11h 35m
1 stop
Depart: Thu Nov 9 2017 Return: Sun Nov 12 2017 Trip spans 4 days
Delta
Delta
MDW
12:00a
KIN
12:25p
12h 25m
1 stop
KIN
12:00a
MDW
12:45p
12h 45m
1 stop
Depart: Sat Dec 9 2017 Return: Sat Dec 16 2017 Trip spans 8 days
Delta
Delta
MDW
12:00a
KIN
7:48a
7h 48m
1 stop
KIN
12:00a
MDW
1:30p
13h 30m
1 stop
Depart: Tue Mar 13 2018 Return: Sat Mar 17 2018 Trip spans 5 days
Delta
Delta
MDW
12:00a
MBJ
9:30a
9h 30m
1 stop
MBJ
12:00a
MDW
7:30a
7h 30m
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.

We compile tonnes of data for you
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

Chicago
$453
Destination

Montego Bay
$453
Kingston
$507
Airlines