$156+ Cheap flights from Midway (MDW) to Jamaica
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Jamaica with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Midway to JamaicaExplore the most affordable flight options available from Midway to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
Explore the most affordable flight options available from Midway to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
This FlightHub deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:42 pm -
1 stop19h 47m
Sun 11/14:43 pm -
1 stop8h 04m
Deal found 8/20![Frontier logo]()
$433
This Justfly.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:46 pm -
1 stop17h 16m
Mon 9/143:42 pm -
1 stop8h 02m
Deal found 8/20![Frontier logo]()
$434
This Justfly.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:03 pm -
1 stop25h 21m
Sat 11/143:39 pm -
1 stop7h 14m
Deal found 8/19![Frontier logo]()
$443
This Priceline deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/87:25 am -
1 stop5h 59m
Thu 11/123:39 pm -
1 stop20h 19m
Deal found 8/19![Frontier logo]()
$451
This Frontier deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:15 am -
1 stop8h 18m
Thu 10/223:48 pm -
1 stop7h 55m
Deal found 8/19![Frontier logo]()
$452
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:04 am -
1 stop5h 47m
Thu 10/221:16 pm -
1 stop9h 17m
Deal found 8/19![Delta logo]()
$462
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:01 pm -
2 stops16h 50m
Mon 10/191:16 pm -
2 stops23h 31m
Deal found 8/19![Delta logo]()
$467
This Frontier deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:15 am -
1 stop8h 18m
Fri 10/233:48 pm -
1 stop7h 55m
Deal found 8/19![Frontier logo]()
$472
This FlightHub deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:25 am -
1 stop8h 02m
Mon 9/283:42 pm -
1 stop8h 02m
Deal found 8/18![Frontier logo]()
$475
This Justfly.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:46 pm -
1 stop19h 41m
Thu 9/173:42 pm -
1 stop8h 02m
Deal found 8/18![Frontier logo]()
$485
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/28:25 pm -
2 stops17h 20m
Fri 11/63:25 pm -
1 stop8h 40m
Deal found 8/19![Southwest logo]()
$490
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/83:20 pm -
1 stop23h 10m
Sat 9/123:30 pm -
1 stop19h 30m
Deal found 8/19![Multiple Airlines logo]()
$707
Best flights from Midway to JamaicaDiscover carefully curated flight deals from Midway to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
Discover carefully curated flight deals from Midway to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/236:00 am -
1 stop7h 10m
Sat 1/303:40 pm -
1 stop7h 30m
Deal found 8/17![Delta logo]()
$519
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/278:40 pm -
2 stops17h 40m
Fri 12/41:00 pm -
1 stop9h 25m
Deal found 8/16![Southwest logo]()
$542
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:30 am -
1 stop6h 25m
Wed 10/712:00 pm -
1 stop6h 35m
Deal found 8/16![Southwest logo]()
$548
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:04 am -
1 stop6h 56m
Tue 11/103:40 pm -
1 stop8h 16m
Deal found 8/16![Delta logo]()
$548
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:00 am -
1 stop7h 25m
Mon 12/73:45 pm -
1 stop6h 30m
Deal found 8/20![Southwest logo]()
$548
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:00 am -
1 stop6h 50m
Tue 10/612:50 pm -
1 stop8h 30m
Deal found 8/17![Southwest logo]()
$582
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/155:25 pm -
1 stop16h 45m
Thu 2/182:20 pm -
1 stop8h 50m
Deal found 8/20![Delta logo]()
$643
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/105:25 pm -
1 stop16h 45m
Wed 2/174:10 pm -
2 stops21h 23m
Deal found 8/20![Delta logo]()
$648
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:55 pm -
2 stops16h 10m
Tue 10/2712:50 pm -
1 stop8h 30m
Deal found 8/20![Southwest logo]()
$593
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/57:20 pm -
2 stops18h 40m
Fri 2/122:00 pm -
1 stop10h 05m
Deal found 8/18![Southwest logo]()
$594
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:10 am -
1 stop6h 35m
Sun 11/151:50 pm -
2 stops10h 15m
Deal found 8/19![Southwest logo]()
$608
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:48 am -
1 stop9h 22m
Mon 9/219:10 am -
1 stop7h 05m
Deal found 8/16![Delta logo]()
$824
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:04 am -
1 stop14h 11m
Wed 10/219:15 am -
1 stop13h 18m
Deal found 8/20![Delta logo]()
$824
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:28 am -
1 stop6h 32m
Sun 11/159:00 am -
1 stop8h 14m
Deal found 8/17![Delta logo]()
$824
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:00 pm -
1 stop7h 10m
Wed 10/79:15 am -
1 stop6h 59m
Deal found 8/16![Delta logo]()
$824
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:29 am -
2 stops10h 41m
Fri 9/259:10 am -
1 stop13h 34m
Deal found 8/16![Delta logo]()
$829
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:05 am -
1 stop14h 08m
Sun 9/139:10 am -
1 stop7h 05m
Deal found 8/19![Delta logo]()
$890
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:35 am -
1 stop8h 35m
Sat 9/199:10 am -
1 stop13h 34m
Deal found 8/20![Delta logo]()
$933
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:35 pm -
1 stop7h 35m
Fri 10/99:15 am -
1 stop13h 18m
Deal found 8/18![Delta logo]()
$933
Last-minute flights from Midway to JamaicaDiscover last-minute flight deals from Midway to Jamaica. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jamaica. Data last updated August 21, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:42 pm -
2 stops25h 31m
Thu 8/279:13 am -
2 stops27h 26m
Deal found 8/17![Delta logo]()
$829
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/83:20 pm -
1 stop23h 10m
Sat 9/123:30 pm -
1 stop19h 30m
Deal found 8/19![Multiple Airlines logo]()
$707
This Justfly.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:46 pm -
1 stop19h 41m
Thu 9/173:42 pm -
1 stop8h 02m
Deal found 8/18![Frontier logo]()
$485
This CheapOair deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:46 pm -
1 stop19h 41m
Sun 9/203:42 pm -
2 stops20h 17m
Deal found 8/18![Frontier logo]()
$503
This Justfly.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:46 pm -
1 stop19h 41m
Mon 9/143:42 pm -
1 stop8h 02m
Deal found 8/17![Frontier logo]()
$504
This Frontier deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:25 am -
1 stop8h 02m
Sun 9/133:42 pm -
1 stop8h 02m
Deal found 8/18![Frontier logo]()
$517
This Justfly.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:46 pm -
1 stop17h 16m
Mon 9/143:42 pm -
1 stop8h 02m
Deal found 8/20![Frontier logo]()
$434
This FlightHub deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:46 pm -
1 stop19h 41m
Sat 9/191:17 pm -
1 stop28h 29m
Deal found 8/20![Frontier logo]()
$467
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:10 am -
1 stop7h 15m
Thu 9/242:15 pm -
2 stops8h 10m
Deal found 8/17![Southwest logo]()
$510
This FlightHub deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:25 am -
1 stop8h 02m
Mon 9/283:42 pm -
1 stop8h 02m
Deal found 8/18![Frontier logo]()
$475
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:55 am -
1 stop6h 30m
Sat 10/312:55 pm -
1 stop9h 20m
Deal found 8/16![Southwest logo]()
$462
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:00 pm -
1 stop7h 10m
Wed 10/79:15 am -
1 stop6h 59m
Deal found 8/16![Delta logo]()
$824
One-way flights from Midway to JamaicaSearch for one-way flight options from Midway to Jamaica. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
Search for one-way flight options from Midway to Jamaica. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This CheapOair deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:15 am -
1 stop8h 18m
Deal found 8/20![Frontier logo]()
$156
This Frontier deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:25 am -
1 stop8h 02m
Deal found 8/18![Frontier logo]()
$157
This FlightHub deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop8h 18m
Deal found 8/18![Frontier logo]()
$159
This FlightHub deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:46 pm -
1 stop17h 16m
Deal found 8/18![Frontier logo]()
$172
This Frontier deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/157:25 am -
1 stop5h 59m
Deal found 8/18![Frontier logo]()
$192
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:00 am -
1 stop7h 25m
Deal found 8/18![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:27 pm -
2 stops22h 03m
Deal found 8/17![Delta logo]()
$213
This Frontier deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:25 am -
1 stop8h 02m
Deal found 8/16![Frontier logo]()
$222
This CheapOair deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:25 am -
1 stop8h 02m
Deal found 8/17![Frontier logo]()
$224
This FlightHub deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:03 pm -
1 stop25h 21m
Deal found 8/18![Frontier logo]()
$233
This FlightHub deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:46 pm -
1 stop19h 41m
Deal found 8/19![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:25 am -
3 stops36h 56m
Deal found 8/17![Multiple Airlines logo]()
$291
Find flight deals from Midway to Jamaica
Keep the following information in mind while searching for Midway to Jamaica flight deals. Data was last updated August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $433 (FlightHub) |
One-way from | $156 (CheapOair) |
Popular in | December |
Cheapest in | September |
Average price | $536 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Jamaica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 21, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Jamaica that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Sat 1/23
6:00 am-2:10 pm
1 stop7h 10m
Montego Bay Sangster Intl
Sat 1/30
3:40 pm-10:10 pm
1 stop7h 30m
$519
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Fri 11/27
8:40 pm-3:20 pm
2 stops17h 40m
Montego Bay Sangster Intl
Fri 12/4
1:00 pm-9:25 pm
1 stop9h 25m
$542
Quickest round-trip
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Wed 9/30
6:30 am-12:55 pm
1 stop6h 25m
Montego Bay Sangster Intl
Wed 10/7
12:00 pm-6:35 pm
1 stop6h 35m
$548
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 11/3
6:04 am-2:00 pm
1 stop6h 56m
Montego Bay Sangster Intl
Tue 11/10
3:40 pm-10:56 pm
1 stop8h 16m
$548
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Fri 12/4
6:00 am-2:25 pm
1 stop7h 25m
Montego Bay Sangster Intl
Mon 12/7
3:45 pm-9:15 pm
1 stop6h 30m
$548
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Thu 10/1
5:00 am-11:50 am
1 stop6h 50m
Montego Bay Sangster Intl
Tue 10/6
12:50 pm-9:20 pm
1 stop8h 30m
$582
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Fri 10/23
8:55 pm-1:05 pm
2 stops16h 10m
Montego Bay Sangster Intl
Tue 10/27
12:50 pm-9:20 pm
1 stop8h 30m
$593
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Fri 2/5
7:20 pm-3:00 pm
2 stops18h 40m
Montego Bay Sangster Intl
Fri 2/12
2:00 pm-11:05 pm
1 stop10h 05m
$594
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Wed 11/11
7:10 am-2:45 pm
1 stop6h 35m
Montego Bay Sangster Intl
Sun 11/15
1:50 pm-11:05 pm
2 stops10h 15m
$608
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Mon 2/15
5:25 pm-11:10 am
1 stop16h 45m
Montego Bay Sangster Intl
Thu 2/18
2:20 pm-10:10 pm
1 stop8h 50m
$643
Showing 1-10 of 37 resultsSorted by cheapest first
Best time to book a flight from Midway to Jamaica
Have a flexible travel schedule? Discover the best time to fly to Jamaica from Midway with our price prediction graph.
MDW-MBJ
MDW-KIN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Jamaica
MDW-JM0
MDW-MBJ
MDW-KIN
What is the cheapest month to book a flight from Chicago Midway Airport to Jamaica?
Currently, December is the cheapest month in which you can book a flight from Chicago Midway Airport to Jamaica (average of $493). Flying from Chicago Midway Airport to Jamaica in March is currently the most expensive (average of $1,144). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Jamaica
Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated August 21, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andFrontier from Chicago Midway Airport to Jamaica to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Midway to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Midway to Jamaica
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Jamaica by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Jamaica by cabin class
Find flights from Midway to Jamaica, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Jamaica flights
Browse other Midway and Jamaica flight options. Last updated on August 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Midway to Jamaica
Discover the top 3 airlines that operate flights from Midway to Jamaica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$172 | Average$552 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$395 | Average$647 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$467 | Average$653 | FlexibilityNo cancel fee | On-time63% |