$118+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Mar 24 — Mar 311
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Jamaica
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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 February 22, 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 February 22, 2026.
This Southwest deal was found by Cheapflights users on 2/20. 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.
Tue 2/246:50 am
MDW
- MBJ
1 stop6h 20m
Southwest
Thu 2/263:10 pm
MBJ
- MDW
1 stop8h 35m
Southwest
Deal found 2/20![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 2/18. 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 4/247:10 am
MDW
- MBJ
1 stop6h 45m
Southwest
Mon 4/272:25 pm
MBJ
- MDW
1 stop9h 15m
Southwest
Deal found 2/18![Southwest logo]()
$336
This Delta deal was found by Cheapflights users on 2/20. 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 4/296:00 am
MDW
- MBJ
1 stop9h 17m
Delta
Sat 5/22:10 pm
MBJ
- MDW
1 stop8h 18m
Delta
Deal found 2/20![Delta logo]()
$352
This Delta deal was found by Cheapflights users on 2/19. 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.
Sat 4/44:30 pm
MDW
- MBJ
2 stops20h 12m
Delta
Wed 4/82:42 pm
MBJ
- MDW
1 stop18h 08m
Delta
Deal found 2/19![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 2/19. 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.
Wed 3/116:00 am
MDW
- MBJ
1 stop9h 28m
Delta
Tue 3/172:42 pm
MBJ
- MDW
1 stop18h 08m
Delta
Deal found 2/19![Delta logo]()
$362
This Southwest deal was found by Cheapflights users on 2/18. 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.
Sat 5/169:55 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Wed 5/202:25 pm
MBJ
- MDW
1 stop7h 00m
Southwest
Deal found 2/18![Southwest logo]()
$365
This Delta deal was found by Cheapflights users on 2/18. 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.
Mon 3/237:20 pm
MDW
- MBJ
1 stop18h 07m
Delta
Thu 3/262:42 pm
MBJ
- MDW
1 stop18h 08m
Delta
Deal found 2/18![Delta logo]()
$368
This Southwest deal was found by Cheapflights users on 2/19. 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.
Sat 4/119:55 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Wed 4/1512:15 pm
MBJ
- MDW
1 stop9h 10m
Southwest
Deal found 2/19![Southwest logo]()
$371
This Delta deal was found by Cheapflights users on 2/18. 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.
Sat 5/166:30 am
MDW
- MBJ
1 stop8h 59m
Delta
Wed 5/2012:55 pm
MBJ
- MDW
1 stop8h 14m
Delta
Deal found 2/18![Delta logo]()
$372
This Southwest deal was found by Cheapflights users on 2/18. 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.
Sat 5/169:55 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Sat 5/2311:35 am
MBJ
- MDW
Nonstop4h 10m
Southwest
Deal found 2/18![Southwest logo]()
$376
This Delta deal was found by Cheapflights users on 2/18. 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.
Sun 3/16:00 am
MDW
- MBJ
1 stop8h 19m
Delta
Wed 3/1111:15 am
MBJ
- MDW
1 stop11h 16m
Delta
Deal found 2/18![Delta logo]()
$382
This Delta deal was found by Cheapflights users on 2/18. 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.
Tue 4/1412:52 pm
MDW
- KIN
1 stop7h 08m
Delta
Tue 4/219:00 am
KIN
- MDW
1 stop13h 28m
Delta
Deal found 2/18![Delta logo]()
$496
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 February 22, 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 February 22, 2026.
This Delta deal was found by Cheapflights users on 2/20. 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 4/296:00 am
MDW
- MBJ
1 stop9h 17m
Delta
Sat 5/22:10 pm
MBJ
- MDW
1 stop8h 18m
Delta
Deal found 2/20![Delta logo]()
$352
This Southwest deal was found by Cheapflights users on 2/17. 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.
Sat 4/186:10 am
MDW
- MBJ
1 stop7h 20m
Southwest
Thu 4/232:25 pm
MBJ
- MDW
2 stops8h 20m
Southwest
Deal found 2/17![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 2/18. 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 5/16:00 am
MDW
- MBJ
1 stop9h 17m
Delta
Wed 5/612:44 pm
MBJ
- MDW
1 stop9h 44m
Delta
Deal found 2/18![Delta logo]()
$352
This Delta deal was found by Cheapflights users on 2/19. 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.
Wed 3/116:00 am
MDW
- MBJ
1 stop9h 28m
Delta
Wed 3/182:42 pm
MBJ
- MDW
1 stop18h 08m
Delta
Deal found 2/19![Delta logo]()
$362
This Southwest deal was found by Cheapflights users on 2/18. 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 3/176:30 am
MDW
- MBJ
1 stop8h 00m
Southwest
Sun 3/2212:30 pm
MBJ
- MDW
Nonstop4h 20m
Southwest
Deal found 2/18![Southwest logo]()
$407
This Delta deal was found by Cheapflights users on 2/19. 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.
Sat 5/96:30 am
MDW
- MBJ
1 stop8h 59m
Delta
Sat 5/162:40 pm
MBJ
- MDW
1 stop6h 29m
Delta
Deal found 2/19![Delta logo]()
$368
This Southwest deal was found by Cheapflights users on 2/19. 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.
Sat 2/288:20 am
MDW
- MBJ
Nonstop3h 55m
Southwest
Fri 3/64:30 pm
MBJ
- MDW
1 stop8h 05m
Southwest
Deal found 2/19![Southwest logo]()
$408
This Delta deal was found by Cheapflights users on 2/18. 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.
Sat 5/166:30 am
MDW
- MBJ
1 stop8h 59m
Delta
Wed 5/2012:55 pm
MBJ
- MDW
1 stop8h 14m
Delta
Deal found 2/18![Delta logo]()
$372
This Delta deal was found by Cheapflights users on 2/18. 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.
Tue 3/177:20 pm
MDW
- MBJ
1 stop18h 07m
Delta
Tue 3/244:49 pm
MBJ
- MDW
1 stop17h 07m
Delta
Deal found 2/18![Delta logo]()
$372
This Delta deal was found by Cheapflights users on 2/18. 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.
Sun 3/16:00 am
MDW
- MBJ
1 stop8h 19m
Delta
Wed 3/1111:15 am
MBJ
- MDW
1 stop11h 16m
Delta
Deal found 2/18![Delta logo]()
$382
This Delta deal was found by Cheapflights users on 2/18. 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.
Mon 3/26:00 am
MDW
- MBJ
1 stop5h 53m
Delta
Wed 3/1111:15 am
MBJ
- MDW
1 stop11h 16m
Delta
Deal found 2/18![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 2/18. 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.
Tue 4/1412:52 pm
MDW
- KIN
1 stop7h 08m
Delta
Tue 4/219:00 am
KIN
- MDW
1 stop13h 28m
Delta
Deal found 2/18![Delta logo]()
$496
This Delta deal was found by Cheapflights users on 2/19. 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.
Sat 5/169:22 am
MDW
- KIN
2 stops10h 43m
Delta
Tue 5/199:00 am
KIN
- MDW
1 stop12h 09m
Delta
Deal found 2/19![Delta logo]()
$571
This Delta deal was found by Cheapflights users on 2/19. 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.
Sat 3/711:06 am
MDW
- KIN
1 stop7h 54m
Delta
Sat 3/149:00 am
KIN
- MDW
1 stop13h 31m
Delta
Deal found 2/19![Delta logo]()
$576
This Delta deal was found by Cheapflights users on 2/18. 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.
Tue 3/1012:47 pm
MDW
- KIN
1 stop7h 13m
Delta
Sat 3/149:00 am
KIN
- MDW
1 stop13h 31m
Delta
Deal found 2/18![Delta logo]()
$580
This Delta deal was found by Cheapflights users on 2/19. 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.
Thu 3/1212:47 pm
MDW
- KIN
1 stop7h 13m
Delta
Sun 3/159:00 am
KIN
- MDW
1 stop13h 31m
Delta
Deal found 2/19![Delta logo]()
$580
This Delta deal was found by Cheapflights users on 2/19. 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 3/66:20 pm
MDW
- KIN
2 stops24h 40m
Delta
Sat 3/149:00 am
KIN
- MDW
1 stop13h 31m
Delta
Deal found 2/19![Delta logo]()
$629
This Delta deal was found by Cheapflights users on 2/19. 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.
Thu 5/286:30 am
MDW
- KIN
1 stop13h 35m
Delta
Tue 6/29:00 am
KIN
- MDW
1 stop12h 09m
Delta
Deal found 2/19![Delta logo]()
$636
This Delta deal was found by Cheapflights users on 2/19. 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.
Thu 3/510:49 am
MDW
- KIN
1 stop8h 11m
Delta
Tue 3/109:00 am
KIN
- MDW
1 stop8h 22m
Delta
Deal found 2/19![Delta logo]()
$664
This Delta deal was found by Cheapflights users on 2/19. 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.
Thu 3/510:49 am
MDW
- KIN
1 stop8h 11m
Delta
Wed 3/119:00 am
KIN
- MDW
1 stop8h 22m
Delta
Deal found 2/19![Delta logo]()
$664
This Delta deal was found by Cheapflights users on 2/19. 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.
Wed 3/1112:47 pm
MDW
- KIN
1 stop7h 13m
Delta
Tue 3/179:00 am
KIN
- MDW
1 stop8h 22m
Delta
Deal found 2/19![Delta logo]()
$664
Last-minute flights from Midway to JamaicaDiscover last-minute flight deals from Midway to Jamaica. Data last updated February 22, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jamaica. Data last updated February 22, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 2/19. 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 2/236:50 am
MDW
- MBJ
1 stop6h 20m
Southwest
Tue 3/32:00 pm
MBJ
- MDW
1 stop8h 00m
Southwest
Deal found 2/19![Southwest logo]()
$398
This Southwest deal was found by Cheapflights users on 2/20. 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.
Tue 2/246:50 am
MDW
- MBJ
1 stop6h 20m
Southwest
Thu 2/263:10 pm
MBJ
- MDW
1 stop8h 35m
Southwest
Deal found 2/20![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 2/18. 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.
Sat 2/288:20 am
MDW
- MBJ
Nonstop3h 55m
Southwest
Tue 3/32:00 pm
MBJ
- MDW
1 stop8h 00m
Southwest
Deal found 2/18![Southwest logo]()
$408
This Delta deal was found by Cheapflights users on 2/18. 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.
Sun 3/16:00 am
MDW
- MBJ
1 stop8h 19m
Delta
Wed 3/1111:15 am
MBJ
- MDW
1 stop11h 16m
Delta
Deal found 2/18![Delta logo]()
$382
This Delta deal was found by Cheapflights users on 2/20. 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 3/26:00 am
MDW
- MBJ
1 stop5h 53m
Delta
Wed 3/1111:15 am
MBJ
- MDW
1 stop11h 16m
Delta
Deal found 2/20![Delta logo]()
$372
This Delta deal was found by Cheapflights users on 2/19. 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.
Sat 3/711:06 am
MDW
- KIN
1 stop7h 54m
Delta
Sat 3/149:00 am
KIN
- MDW
1 stop13h 31m
Delta
Deal found 2/19![Delta logo]()
$576
This Delta deal was found by Cheapflights users on 2/18. 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.
Tue 3/1012:47 pm
MDW
- KIN
1 stop7h 13m
Delta
Sat 3/149:00 am
KIN
- MDW
1 stop13h 31m
Delta
Deal found 2/18![Delta logo]()
$580
This Delta deal was found by Cheapflights users on 2/19. 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.
Wed 3/116:00 am
MDW
- MBJ
1 stop9h 28m
Delta
Tue 3/172:42 pm
MBJ
- MDW
1 stop18h 08m
Delta
Deal found 2/19![Delta logo]()
$362
This Delta deal was found by Cheapflights users on 2/19. 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 3/166:34 pm
MDW
- MBJ
2 stops16h 47m
Delta
Wed 3/182:42 pm
MBJ
- MDW
1 stop18h 08m
Delta
Deal found 2/19![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 2/18. 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 3/176:30 am
MDW
- MBJ
1 stop8h 00m
Southwest
Sun 3/2212:30 pm
MBJ
- MDW
Nonstop4h 20m
Southwest
Deal found 2/18![Southwest logo]()
$407
This Delta deal was found by Cheapflights users on 2/18. 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.
Mon 3/237:20 pm
MDW
- MBJ
1 stop18h 07m
Delta
Thu 3/262:42 pm
MBJ
- MDW
1 stop18h 08m
Delta
Deal found 2/18![Delta logo]()
$368
This Delta deal was found by Cheapflights users on 2/19. 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 3/316:00 am
MDW
- MBJ
1 stop9h 28m
Delta
Wed 4/82:42 pm
MBJ
- MDW
1 stop18h 08m
Delta
Deal found 2/19![Delta logo]()
$352
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 February 22, 2026.
Search for one-way flight options from Midway to Jamaica. Find affordable one-way fares based on user searches. Data last updated February 22, 2026.
This Southwest deal was found by Cheapflights users on 2/20. 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.
Sat 5/169:55 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Deal found 2/20![Southwest logo]()
$118
This Southwest deal was found by Cheapflights users on 2/19. 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 4/275:35 am
MDW
- MBJ
1 stop6h 00m
Southwest
Deal found 2/19![Southwest logo]()
$122
This Southwest deal was found by Cheapflights users on 2/18. 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 3/246:30 am
MDW
- MBJ
1 stop8h 00m
Southwest
Deal found 2/18![Southwest logo]()
$123
This Southwest deal was found by Cheapflights users on 2/21. 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 4/119:55 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Deal found 2/21![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 2/21. 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 4/46:25 am
MDW
- MBJ
1 stop5h 45m
Southwest
Deal found 2/21![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 2/18. 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 3/176:30 am
MDW
- MBJ
1 stop8h 00m
Southwest
Deal found 2/18![Southwest logo]()
$133
This Southwest deal was found by Cheapflights users on 2/18. 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.
Sat 4/186:10 am
MDW
- MBJ
1 stop7h 20m
Southwest
Deal found 2/18![Southwest logo]()
$134
This Trip.com deal was found by Cheapflights users on 2/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:00 am
MDW
- MBJ
1 stop8h 23m
Frontier
Deal found 2/20![Frontier logo]()
$140
This Southwest deal was found by Cheapflights users on 2/21. 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 3/46:50 am
MDW
- MBJ
1 stop6h 20m
Southwest
Deal found 2/21![Southwest logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/112:56 pm
MDW
- MBJ
1 stop23h 27m
Frontier
Deal found 2/20![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Sun 3/156:00 am
MDW
- KIN
2 stops26h 10m
Multiple Airlines
Deal found 2/19![Multiple Airlines logo]()
$306
This Delta deal was found by Cheapflights users on 2/19. 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.
Sun 3/156:00 am
MDW
- KIN
1 stop14h 00m
Delta
Deal found 2/19![Delta logo]()
$331
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 February 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $312 (Southwest) |
One-way from | $118 (Southwest) |
Popular in | June |
Cheapest in | January |
Average price | $546 |
Good round-trip deal | $660 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 February 22, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Jamaica that are best for you.
Fly from
Midway
Fly to
Jamaica
Route
Depart
Return
Price
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Wed 4/29
6:00 am-3:17 pm
1 stop9h 17m
Montego Bay Sangster Intl
Sat 5/2
2:10 pm-10:28 pm
1 stop8h 18m
$352
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Fri 5/1
6:00 am-3:17 pm
1 stop9h 17m
Montego Bay Sangster Intl
Wed 5/6
12:44 pm-10:28 pm
1 stop9h 44m
$352
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Wed 3/11
6:00 am-3:28 pm
1 stop9h 28m
Montego Bay Sangster Intl
Wed 3/18
2:42 pm-8:50 am
1 stop18h 08m
$362
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 5/9
6:30 am-3:29 pm
1 stop8h 59m
Montego Bay Sangster Intl
Sat 5/16
2:40 pm-9:09 pm
1 stop6h 29m
$368
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 5/16
6:30 am-3:29 pm
1 stop8h 59m
Montego Bay Sangster Intl
Wed 5/20
12:55 pm-9:09 pm
1 stop8h 14m
$372
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Tue 3/17
7:20 pm-1:27 pm
1 stop18h 07m
Montego Bay Sangster Intl
Tue 3/24
4:49 pm-9:56 am
1 stop17h 07m
$372
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 4/18
6:10 am-1:30 pm
1 stop7h 20m
Montego Bay Sangster Intl
Thu 4/23
2:25 pm-10:45 pm
2 stops8h 20m
$382
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 3/1
6:00 am-3:19 pm
1 stop8h 19m
Montego Bay Sangster Intl
Wed 3/11
11:15 am-10:31 pm
1 stop11h 16m
$382
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 3/2
6:00 am-12:53 pm
1 stop5h 53m
Montego Bay Sangster Intl
Wed 3/11
11:15 am-10:31 pm
1 stop11h 16m
$402
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Tue 3/17
6:30 am-2:30 pm
1 stop8h 00m
Montego Bay Sangster Intl
Sun 3/22
12:30 pm-4:50 pm
Nonstop4h 20m
$407
Showing 1-10 of 34 results
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 $384). Flying from Chicago Midway Airport to Jamaica in November is currently the most expensive (average of $580). 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.
What is the cheapest time of day to fly from MDW to JM?
Find hourly flight availability from Midway to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 22, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Jamaica as you normally would.
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 February 22, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and Frontier 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.
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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
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 February 22, 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 February 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$446 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$395 | Average$606 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$518 | Average$693 | FlexibilityNo cancel fee | On-time63% |