$108+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
May 28 — Jun 41
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Jamaica with Cheapflights
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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 April 28, 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 April 28, 2026.
This Southwest deal was found by Cheapflights users on 4/24. 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 7/267:50 am
MDW
- MBJ
Nonstop3h 55m
Southwest
Thu 7/301:50 pm
MBJ
- MDW
Nonstop4h 00m
Southwest
Deal found 4/24![Southwest logo]()
$318
This FlightHub deal was found by Cheapflights users on 4/24. 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.
Sat 5/911:59 am
MDW
- MBJ
1 stop24h 12m
Frontier
Wed 5/131:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/24![Frontier logo]()
$321
This Frontier deal was found by Cheapflights users on 4/27. 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.
Tue 5/56:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 5/121:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/27![Frontier logo]()
$328
This Frontier deal was found by Cheapflights users on 4/26. 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.
Mon 5/116:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Fri 5/151:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/26![Frontier logo]()
$348
This Priceline deal was found by Cheapflights users on 4/27. 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 5/106:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Wed 5/131:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/27![Frontier logo]()
$349
This Frontier deal was found by Cheapflights users on 4/26. 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.
Tue 5/266:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Sat 5/301:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/26![Frontier logo]()
$362
This Priceline deal was found by Cheapflights users on 4/24. 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.
Thu 5/712:19 pm
MDW
- MBJ
1 stop23h 52m
Frontier
Sun 5/101:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/24![Frontier logo]()
$367
This Orbitz deal was found by Cheapflights users on 4/27. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Wed 8/51:32 pm
MBJ
- MDW
1 stop8h 36m
Frontier
Deal found 4/27![Frontier logo]()
$372
This FlightHub deal was found by Cheapflights users on 4/23. 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.
Sat 5/911:59 am
MDW
- MBJ
1 stop24h 12m
Frontier
Tue 5/121:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/23![Frontier logo]()
$376
This Delta deal was found by Cheapflights users on 4/27. 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 9/1910:35 am
MDW
- KIN
1 stop8h 55m
Delta
Sat 9/269:00 am
KIN
- MDW
1 stop12h 46m
Delta
Deal found 4/27![Delta logo]()
$576
This Kiwi.com deal was found by Cheapflights users on 4/24. 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.
Thu 6/1812:27 pm
MDW
- KIN
2 stops23h 28m
Multiple Airlines
Mon 6/226:25 pm
KIN
- MDW
1 stop15h 15m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$612
This Kissandfly.com deal was found by Cheapflights users on 4/24. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:23 am
MDW
- KIN
1 stop13h 37m
KLM
Thu 5/219:00 am
KIN
- MDW
1 stop12h 09m
KLM
Deal found 4/24![KLM logo]()
$648
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 April 28, 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 April 28, 2026.
This Southwest deal was found by Cheapflights users on 4/24. 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 7/18:10 am
MDW
- MBJ
1 stop6h 45m
Southwest
Sun 7/52:30 pm
MBJ
- MDW
Nonstop4h 05m
Southwest
Deal found 4/24![Southwest logo]()
$460
This Delta deal was found by Cheapflights users on 4/27. 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 9/216:00 am
MDW
- MBJ
1 stop9h 34m
Delta
Sat 9/261:25 pm
MBJ
- MDW
1 stop8h 21m
Delta
Deal found 4/27![Delta logo]()
$513
This Southwest deal was found by Cheapflights users on 4/26. 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 6/295:10 am
MDW
- MBJ
2 stops9h 45m
Southwest
Sun 7/52:30 pm
MBJ
- MDW
Nonstop4h 05m
Southwest
Deal found 4/26![Southwest logo]()
$490
This Delta deal was found by Cheapflights users on 4/27. 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 9/1910:35 am
MDW
- KIN
1 stop8h 55m
Delta
Sat 9/269:00 am
KIN
- MDW
2 stops9h 31m
Delta
Deal found 4/27![Delta logo]()
$581
This Southwest deal was found by Cheapflights users on 4/25. 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 6/2010:10 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Wed 6/243:55 pm
MBJ
- MDW
1 stop7h 55m
Southwest
Deal found 4/25![Southwest logo]()
$541
This Southwest deal was found by Cheapflights users on 4/27. 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 7/155:10 am
MDW
- MBJ
1 stop5h 35m
Southwest
Sun 7/192:30 pm
MBJ
- MDW
Nonstop4h 05m
Southwest
Deal found 4/27![Southwest logo]()
$555
This Delta deal was found by Cheapflights users on 4/24. 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 9/236:00 am
MDW
- KIN
1 stop13h 30m
Delta
Sun 9/279:00 am
KIN
- MDW
1 stop12h 46m
Delta
Deal found 4/24![Delta logo]()
$660
This Southwest deal was found by Cheapflights users on 4/23. 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 5/117:30 am
MDW
- MBJ
1 stop6h 25m
Southwest
Fri 5/1512:15 pm
MBJ
- MDW
2 stops8h 00m
Southwest
Deal found 4/23![Southwest logo]()
$577
This Delta deal was found by Cheapflights users on 4/27. 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 9/410:35 am
MDW
- KIN
1 stop9h 29m
Delta
Sun 9/139:00 am
KIN
- MDW
1 stop12h 46m
Delta
Deal found 4/27![Delta logo]()
$660
This Southwest deal was found by Cheapflights users on 4/25. 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 8/275:00 am
MDW
- MBJ
1 stop8h 15m
Southwest
Mon 8/3112:15 pm
MBJ
- MDW
2 stops9h 40m
Southwest
Deal found 4/25![Southwest logo]()
$618
This Delta deal was found by Cheapflights users on 4/25. 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 8/2110:35 am
MDW
- KIN
1 stop9h 29m
Delta
Sun 8/239:00 am
KIN
- MDW
1 stop12h 46m
Delta
Deal found 4/25![Delta logo]()
$744
This Southwest deal was found by Cheapflights users on 4/26. 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 7/46:50 am
MDW
- MBJ
1 stop6h 40m
Southwest
Tue 7/711:45 am
MBJ
- MDW
2 stops8h 05m
Southwest
Deal found 4/26![Southwest logo]()
$653
This Delta deal was found by Cheapflights users on 4/25. 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 6/86:05 am
MDW
- KIN
1 stop13h 55m
Delta
Wed 6/179:00 am
KIN
- MDW
1 stop13h 17m
Delta
Deal found 4/25![Delta logo]()
$744
This Delta deal was found by Cheapflights users on 4/27. 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 9/36:00 am
MDW
- KIN
1 stop14h 04m
Delta
Mon 9/79:00 am
KIN
- MDW
2 stops9h 31m
Delta
Deal found 4/27![Delta logo]()
$749
This Delta deal was found by Cheapflights users on 4/22. 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 5/2310:45 am
MDW
- KIN
1 stop9h 15m
Delta
Sat 5/309:00 am
KIN
- MDW
1 stop12h 09m
Delta
Deal found 4/22![Delta logo]()
$794
This Delta deal was found by Cheapflights users on 4/22. 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 10/149:30 am
MDW
- KIN
2 stops10h 00m
Delta
Mon 10/199:00 am
KIN
- MDW
2 stops9h 37m
Delta
Deal found 4/22![Delta logo]()
$799
Last-minute flights from Midway to JamaicaDiscover last-minute flight deals from Midway to Jamaica. Data last updated April 28, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jamaica. Data last updated April 28, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 4/23. 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.
Sun 5/312:52 pm
MDW
- KIN
1 stop7h 08m
Delta
Mon 5/119:00 am
KIN
- MDW
1 stop12h 09m
Delta
Deal found 4/23![Delta logo]()
$788
This Frontier deal was found by Cheapflights users on 4/27. 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.
Tue 5/56:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 5/121:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/27![Frontier logo]()
$328
This Priceline deal was found by Cheapflights users on 4/24. 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.
Thu 5/712:19 pm
MDW
- MBJ
1 stop23h 52m
Frontier
Sun 5/101:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/24![Frontier logo]()
$367
This Delta deal was found by Cheapflights users on 4/23. 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 5/712:53 pm
MDW
- KIN
1 stop7h 07m
Delta
Tue 5/129:00 am
KIN
- MDW
1 stop12h 09m
Delta
Deal found 4/23![Delta logo]()
$744
This FlightHub deal was found by Cheapflights users on 4/24. 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.
Sat 5/911:59 am
MDW
- MBJ
1 stop24h 12m
Frontier
Wed 5/131:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/24![Frontier logo]()
$321
This FlightHub deal was found by Cheapflights users on 4/23. 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.
Sat 5/911:59 am
MDW
- MBJ
1 stop24h 12m
Frontier
Tue 5/121:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/23![Frontier logo]()
$376
This Priceline deal was found by Cheapflights users on 4/27. 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 5/106:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Wed 5/131:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/27![Frontier logo]()
$349
This Frontier deal was found by Cheapflights users on 4/26. 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.
Mon 5/116:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Fri 5/151:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/26![Frontier logo]()
$348
This Frontier deal was found by Cheapflights users on 4/24. 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.
Mon 5/116:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Thu 5/141:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/24![Frontier logo]()
$392
This Kissandfly.com deal was found by Cheapflights users on 4/24. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:23 am
MDW
- KIN
1 stop13h 37m
KLM
Thu 5/219:00 am
KIN
- MDW
1 stop12h 09m
KLM
Deal found 4/24![KLM logo]()
$648
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Sun 5/2412:27 pm
MDW
- KIN
2 stops22h 40m
Multiple Airlines
Sun 5/318:05 am
KIN
- MDW
1 stop25h 35m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$779
This Frontier deal was found by Cheapflights users on 4/26. 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.
Tue 5/266:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Sat 5/301:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 4/26![Frontier logo]()
$362
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 April 28, 2026.
Search for one-way flight options from Midway to Jamaica. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
This Priceline deal was found by Cheapflights users on 4/27. 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.
Tue 5/196:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 4/27![Frontier logo]()
$108
This Southwest deal was found by Cheapflights users on 4/23. 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 7/2210:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Deal found 4/23![Southwest logo]()
$138
This Frontier deal was found by Cheapflights users on 4/27. 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.
Tue 5/266:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 4/27![Frontier logo]()
$152
This Frontier deal was found by Cheapflights users on 4/27. 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.
Wed 6/36:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 4/27![Frontier logo]()
$162
This Frontier deal was found by Cheapflights users on 4/23. 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 5/156:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 4/23![Frontier logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
Thu 5/146:00 am
MDW
- MBJ
1 stop30h 11m
Frontier
Deal found 4/23![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Sun 5/246:00 am
MDW
- MBJ
1 stop30h 11m
Frontier
Deal found 4/27![Frontier logo]()
$179
This Frontier deal was found by Cheapflights users on 4/27. 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.
Sat 7/186:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Deal found 4/27![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Sat 5/2311:59 am
MDW
- MBJ
2 stops24h 32m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Mon 5/256:00 am
MDW
- MBJ
1 stop30h 11m
Frontier
Deal found 4/27![Frontier logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
Mon 5/116:00 am
MDW
- MBJ
2 stops30h 31m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 9/112:27 pm
MDW
- KIN
2 stops23h 28m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$241
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 April 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $318 (Southwest) |
One-way from | $108 (Priceline) |
Popular in | June |
Cheapest in | January |
Average price | $522 |
Good round-trip deal | $517 or less |
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 2,558,603 searches. Data last updated April 28, 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 - MBJ
MDWMBJ
Chicago Midway
Wed 7/1
8:10 am-2:55 pm
1 stop6h 45m
Montego Bay Sangster Intl
Sun 7/5
2:30 pm-6:35 pm
Nonstop4h 05m
$460
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 6/29
5:10 am-2:55 pm
2 stops9h 45m
Montego Bay Sangster Intl
Sun 7/5
2:30 pm-6:35 pm
Nonstop4h 05m
$490
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 9/21
6:00 am-3:34 pm
1 stop9h 34m
Montego Bay Sangster Intl
Sat 9/26
1:25 pm-9:46 pm
1 stop8h 21m
$513
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 6/20
10:10 am-2:00 pm
Nonstop3h 50m
Montego Bay Sangster Intl
Wed 6/24
3:55 pm-11:50 pm
1 stop7h 55m
$541
Quickest round-trip
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Wed 7/15
5:10 am-10:45 am
1 stop5h 35m
Montego Bay Sangster Intl
Sun 7/19
2:30 pm-6:35 pm
Nonstop4h 05m
$555
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 5/11
7:30 am-1:55 pm
1 stop6h 25m
Montego Bay Sangster Intl
Fri 5/15
12:15 pm-8:15 pm
2 stops8h 00m
$577
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Sat 9/19
10:35 am-7:30 pm
1 stop8h 55m
Kingston Norman Manley
Sat 9/26
9:00 am-6:31 pm
2 stops9h 31m
$581
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Thu 8/27
5:00 am-1:15 pm
1 stop8h 15m
Montego Bay Sangster Intl
Mon 8/31
12:15 pm-9:55 pm
2 stops9h 40m
$618
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 7/4
6:50 am-1:30 pm
1 stop6h 40m
Montego Bay Sangster Intl
Tue 7/7
11:45 am-7:50 pm
2 stops8h 05m
$653
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Wed 9/23
6:00 am-7:30 pm
1 stop13h 30m
Kingston Norman Manley
Sun 9/27
9:00 am-9:46 pm
1 stop12h 46m
$660
Showing 1-10 of 34 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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Jamaica (average of $341). Flying from Chicago Midway Airport to Jamaica in May is currently the most expensive (average of $603). 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 April 28, 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.
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
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Complete your trip
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Midway and Jamaica flights
Browse other Midway and Jamaica flight options. Last updated on April 28, 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 2,558,603 searches. Data last updated April 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$172 | Average$472 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$395 | Average$564 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$468 | Average$653 | FlexibilityNo cancel fee | On-time63% |