Find Deals on Flights from Caribbean 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.
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 Caribbean to Chicago Midway

(Round-trip)
Depart: Thu Jul 6 2017 Return: Mon Jul 10 2017 Trip spans 5 days
Delta
Delta
NAS
MDW
6h 42m
1 stop
MDW
NAS
6h 31m
1 stop
Depart: Wed May 17 2017 Return: Fri May 19 2017 Trip spans 3 days
Delta
Delta
MBJ
MDW
7h 00m
1 stop
MDW
MBJ
8h 09m
1 stop
Depart: Sat Apr 15 2017 Return: Sun May 21 2017 Trip spans 37 days
Delta
Delta
KIN
MDW
11h 19m
1 stop
MDW
KIN
6h 35m
1 stop
Depart: Wed May 10 2017 Return: Fri Jun 9 2017 Trip spans 31 days
Delta
Delta
KIN
MDW
11h 00m
1 stop
MDW
KIN
8h 19m
1 stop
Depart: Wed May 10 2017 Return: Wed May 17 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
7h 18m
1 stop
MDW
SJU
6h 36m
1 stop
Depart: Thu Apr 27 2017 Return: Sun Apr 30 2017 Trip spans 4 days
Delta
Delta
SJU
MDW
7h 18m
1 stop
MDW
SJU
8h 09m
1 stop
Depart: Fri May 12 2017 Return: Mon May 15 2017 Trip spans 4 days
Delta
Delta
SJU
MDW
9h 00m
1 stop
MDW
SJU
6h 25m
1 stop
Depart: Thu Sep 28 2017 Return: Sun Oct 1 2017 Trip spans 4 days
Delta
Delta
SJU
MDW
8h 52m
1 stop
MDW
SJU
6h 54m
1 stop
Depart: Fri Apr 28 2017 Return: Sun Apr 30 2017 Trip spans 3 days
Delta
Delta
SJU
MDW
7h 18m
1 stop
MDW
SJU
8h 09m
1 stop
Depart: Fri May 12 2017 Return: Sun May 21 2017 Trip spans 10 days
Delta
Delta
SJU
MDW
7h 38m
1 stop
MDW
SJU
6h 25m
1 stop
Depart: Sat Sep 16 2017 Return: Sat Sep 30 2017 Trip spans 15 days
Delta
Delta
SJU
MDW
7h 27m
1 stop
MDW
SJU
6h 52m
1 stop
Depart: Tue Apr 18 2017 Return: Sat Apr 22 2017 Trip spans 5 days
Delta
Delta
NAS
MDW
6h 33m
1 stop
MDW
NAS
6h 14m
1 stop
Depart: Fri May 12 2017 Return: Mon May 15 2017 Trip spans 4 days
Delta
Delta
NAS
MDW
8h 05m
1 stop
MDW
NAS
5h 00m
1 stop
Depart: Thu Jun 8 2017 Return: Mon Jun 12 2017 Trip spans 5 days
Delta
Delta
NAS
MDW
13h 00m
1 stop
MDW
NAS
15h 44m
1 stop
Depart: Wed Aug 16 2017 Return: Tue Aug 22 2017 Trip spans 7 days
Delta
Delta
SJU
MDW
6h 42m
1 stop
MDW
SJU
8h 34m
1 stop
Depart: Sun Apr 30 2017 Return: Tue May 2 2017 Trip spans 3 days
Delta
Delta
GCM
MDW
13h 35m
2 stops
MDW
GCM
5h 15m
1 stop
Depart: Wed Aug 2 2017 Return: Mon Aug 7 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
6h 42m
1 stop
MDW
SJU
6h 54m
1 stop
Depart: Sun Aug 13 2017 Return: Sat Aug 19 2017 Trip spans 7 days
Delta
Delta
NAS
MDW
6h 23m
1 stop
MDW
NAS
6h 32m
1 stop
Depart: Tue Jul 11 2017 Return: Tue Jul 25 2017 Trip spans 15 days
Delta
Delta
SJU
MDW
6h 42m
1 stop
MDW
SJU
6h 54m
1 stop
Depart: Fri May 12 2017 Return: Mon May 15 2017 Trip spans 4 days
Delta
Delta
GCM
MDW
8h 45m
1 stop
MDW
GCM
16h 45m
2 stops
* 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

Nassau
$248
San Juan
$390
Montego Bay
$284
Kingston
$362
George Town
$460
Destination

Chicago
$248
Airlines