$148+ 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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Jun 10 — Jun 171
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 May 11, 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 May 11, 2026.
This Priceline deal was found by Cheapflights users on 5/9. 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.
Wed 8/196:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Tue 8/251:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/9![Frontier logo]()
$372
This Frontier deal was found by Cheapflights users on 5/10. 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 8/156:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Tue 8/251:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/10![Frontier logo]()
$386
This Priceline deal was found by Cheapflights users on 5/7. 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 8/1812:27 pm
MDW
- MBJ
1 stop23h 54m
Frontier
Tue 8/251:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/7![Frontier logo]()
$390
This Priceline deal was found by Cheapflights users on 5/9. 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.
Wed 8/196:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Mon 8/241:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/9![Frontier logo]()
$392
This Frontier deal was found by Cheapflights users on 5/10. 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
Fri 7/241:32 pm
MBJ
- MDW
1 stop8h 36m
Frontier
Deal found 5/10![Frontier logo]()
$406
This Gotogate deal was found by Cheapflights users on 5/7. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:11 pm
MDW
- MBJ
1 stop24h 16m
Frontier
Wed 7/151:32 pm
MBJ
- MDW
1 stop8h 36m
Frontier
Deal found 5/7![Frontier logo]()
$410
This Frontier deal was found by Cheapflights users on 5/10. 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 8/166:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Thu 8/201:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/10![Frontier logo]()
$412
This Frontier deal was found by Cheapflights users on 5/9. 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 8/256:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Thu 8/271:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/9![Frontier logo]()
$426
This Mytrip deal was found by Cheapflights users on 5/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2512:11 pm
MDW
- MBJ
1 stop24h 16m
Frontier
Sun 8/21:32 pm
MBJ
- MDW
1 stop8h 36m
Frontier
Deal found 5/6![Frontier logo]()
$429
This Priceline deal was found by Cheapflights users on 5/7. 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 6/96:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Fri 6/121:26 pm
MBJ
- MDW
1 stop21h 38m
Frontier
Deal found 5/7![Frontier logo]()
$430
This Frontier deal was found by Cheapflights users on 5/10. 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 7/266:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Fri 7/311:32 pm
MBJ
- MDW
1 stop8h 36m
Frontier
Deal found 5/10![Frontier logo]()
$432
This Priceline deal was found by Cheapflights users on 5/10. 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
Wed 5/271:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 5/10![Frontier logo]()
$437
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 May 11, 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 May 11, 2026.
This Southwest deal was found by Cheapflights users on 5/9. 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 5/306:10 am
MDW
- MBJ
1 stop7h 20m
Southwest
Sat 6/62:30 pm
MBJ
- MDW
Nonstop4h 05m
Southwest
Deal found 5/9![Southwest logo]()
$469
This Delta deal was found by Cheapflights users on 5/10. 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 6/16:23 am
MDW
- KIN
1 stop13h 37m
Delta
Fri 6/59:00 am
KIN
- MDW
1 stop12h 09m
Delta
Deal found 5/10![Delta logo]()
$576
This Southwest deal was found by Cheapflights users on 5/9. 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 8/95:10 am
MDW
- MBJ
1 stop6h 35m
Southwest
Thu 8/2712:15 pm
MBJ
- MDW
2 stops9h 40m
Southwest
Deal found 5/9![Southwest logo]()
$576
This Southwest deal was found by Cheapflights users on 5/7. 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 5/246:40 am
MDW
- MBJ
1 stop7h 40m
Southwest
Thu 5/2812:35 pm
MBJ
- MDW
2 stops10h 10m
Southwest
Deal found 5/7![Southwest logo]()
$592
This Delta deal was found by Cheapflights users on 5/9. 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 6/610:45 am
MDW
- KIN
1 stop9h 15m
Delta
Sat 6/139:00 am
KIN
- MDW
1 stop13h 17m
Delta
Deal found 5/9![Delta logo]()
$660
This Southwest deal was found by Cheapflights users on 5/8. 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 6/118:55 pm
MDW
- MBJ
2 stops18h 00m
Southwest
Tue 6/1611:45 am
MBJ
- MDW
2 stops8h 05m
Southwest
Deal found 5/8![Southwest logo]()
$602
This Delta deal was found by Cheapflights users on 5/8. 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 5/299:22 am
MDW
- KIN
2 stops10h 38m
Delta
Sun 5/319:00 am
KIN
- MDW
1 stop12h 09m
Delta
Deal found 5/8![Delta logo]()
$665
This Delta deal was found by Cheapflights users on 5/6. 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 5/239:22 am
MDW
- KIN
2 stops10h 38m
Delta
Sat 5/309:00 am
KIN
- MDW
1 stop12h 09m
Delta
Deal found 5/6![Delta logo]()
$665
This Southwest deal was found by Cheapflights users on 5/7. 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 5/7![Southwest logo]()
$609
This Southwest deal was found by Cheapflights users on 5/7. 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 7/255:05 am
MDW
- MBJ
1 stop8h 25m
Southwest
Wed 7/2911:45 am
MBJ
- MDW
2 stops8h 05m
Southwest
Deal found 5/7![Southwest logo]()
$613
This Delta deal was found by Cheapflights users on 5/7. 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 5/1410:59 am
MDW
- KIN
1 stop9h 01m
Delta
Sat 5/309:00 am
KIN
- MDW
1 stop12h 09m
Delta
Deal found 5/7![Delta logo]()
$714
This Southwest deal was found by Cheapflights users on 5/6. 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 7/308:50 pm
MDW
- MBJ
2 stops16h 30m
Southwest
Mon 8/33:55 pm
MBJ
- MDW
1 stop7h 05m
Southwest
Deal found 5/6![Southwest logo]()
$640
This Delta deal was found by Cheapflights users on 5/8. 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 5/2210:59 am
MDW
- KIN
1 stop9h 01m
Delta
Mon 5/259:00 am
KIN
- MDW
1 stop7h 12m
Delta
Deal found 5/8![Delta logo]()
$744
This Southwest deal was found by Cheapflights users on 5/6. 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
Mon 6/222:20 pm
MBJ
- MDW
1 stop10h 20m
Southwest
Deal found 5/6![Southwest logo]()
$649
This Delta deal was found by Cheapflights users on 5/6. 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 6/1112:50 pm
MDW
- KIN
1 stop7h 10m
Delta
Wed 6/179:00 am
KIN
- MDW
1 stop13h 17m
Delta
Deal found 5/6![Delta logo]()
$744
This Southwest deal was found by Cheapflights users on 5/7. 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 6/97:35 pm
MDW
- MBJ
2 stops15h 10m
Southwest
Fri 6/123:55 pm
MBJ
- MDW
1 stop7h 05m
Southwest
Deal found 5/7![Southwest logo]()
$655
This Delta deal was found by Cheapflights users on 5/10. 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 6/126:00 am
MDW
- KIN
1 stop14h 00m
Delta
Tue 6/169:00 am
KIN
- MDW
1 stop13h 17m
Delta
Deal found 5/10![Delta logo]()
$744
This Southwest deal was found by Cheapflights users on 5/6. 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 7/158:10 am
MDW
- MBJ
1 stop6h 15m
Southwest
Mon 7/2011:45 am
MBJ
- MDW
1 stop8h 25m
Southwest
Deal found 5/6![Southwest logo]()
$658
This Southwest deal was found by Cheapflights users on 5/11. 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 6/288:35 pm
MDW
- MBJ
2 stops18h 20m
Southwest
Wed 7/13:55 pm
MBJ
- MDW
1 stop7h 55m
Southwest
Deal found 5/11![Southwest logo]()
$663
Last-minute flights from Midway to JamaicaDiscover last-minute flight deals from Midway to Jamaica. Data last updated May 11, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jamaica. Data last updated May 11, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/6. 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 5/106:23 am
MDW
- MBJ
1 stop9h 11m
Delta
Fri 5/222:22 pm
MBJ
- MDW
1 stop6h 47m
Delta
Deal found 5/6![Delta logo]()
$452
This Priceline deal was found by Cheapflights users on 5/10. 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
Wed 5/271:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 5/10![Frontier logo]()
$437
This Priceline deal was found by Cheapflights users on 5/6. 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.
Sat 5/2311:59 am
MDW
- MBJ
1 stop24h 12m
Frontier
Sat 5/301:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 5/6![Frontier logo]()
$461
This Priceline deal was found by Cheapflights users on 5/7. 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 5/2412:27 pm
MDW
- MBJ
1 stop23h 44m
Frontier
Thu 5/281:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 5/7![Frontier logo]()
$441
This Trip.com deal was found by Cheapflights users on 5/9. 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.
Thu 5/286:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Wed 6/31:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 5/9![Frontier logo]()
$442
This Delta deal was found by Cheapflights users on 5/8. 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 5/296:23 am
MDW
- KIN
1 stop13h 37m
Delta
Sun 5/319:00 am
KIN
- MDW
1 stop12h 09m
Delta
Deal found 5/8![Delta logo]()
$576
This Priceline deal was found by Cheapflights users on 5/9. 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.
Sat 5/306:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Sat 6/61:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 5/9![Frontier logo]()
$426
This Southwest deal was found by Cheapflights users on 5/9. 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 5/309:55 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Sat 6/62:30 pm
MBJ
- MDW
Nonstop4h 05m
Southwest
Deal found 5/9![Southwest logo]()
$446
This Trip.com deal was found by Cheapflights users on 5/10. 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.
Mon 6/16:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Wed 6/31:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 5/10![Frontier logo]()
$444
This Priceline deal was found by Cheapflights users on 5/7. 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 6/96:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Fri 6/121:26 pm
MBJ
- MDW
1 stop21h 38m
Frontier
Deal found 5/7![Frontier logo]()
$430
This Priceline deal was found by Cheapflights users on 5/6. 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 6/96:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Tue 6/161:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/6![Frontier logo]()
$432
This Trip.com deal was found by Cheapflights users on 5/11. 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 6/286:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Wed 7/11:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/11![Frontier logo]()
$445
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 May 11, 2026.
Search for one-way flight options from Midway to Jamaica. Find affordable one-way fares based on user searches. Data last updated May 11, 2026.
This Southwest deal was found by Cheapflights users on 5/7. 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 6/217:50 am
MDW
- MBJ
Nonstop3h 55m
Southwest
Deal found 5/7![Southwest logo]()
$148
This Frontier deal was found by Cheapflights users on 5/10. 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 5/10![Frontier logo]()
$176
This Frontier deal was found by Cheapflights users on 5/6. 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 8/26:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Deal found 5/6![Frontier logo]()
$182
This Frontier deal was found by Cheapflights users on 5/8. 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 5/256:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 5/8![Frontier logo]()
$192
This Priceline deal was found by Cheapflights users on 5/8. 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.
Sat 8/112:11 pm
MDW
- MBJ
1 stop24h 16m
Frontier
Deal found 5/8![Frontier logo]()
$201
This Delta deal was found by Cheapflights users on 5/7. 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 7/56:00 am
MDW
- MBJ
1 stop5h 59m
Delta
Deal found 5/7![Delta logo]()
$202
This Delta deal was found by Cheapflights users on 5/6. 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 5/306:36 pm
MDW
- MBJ
2 stops20h 58m
Delta
Deal found 5/6![Delta logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 5/306:00 am
MDW
- MBJ
1 stop30h 11m
Frontier
Deal found 5/6![Frontier logo]()
$218
This Priceline deal was found by Cheapflights users on 5/10. 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 7/2312:11 pm
MDW
- MBJ
1 stop24h 16m
Frontier
Deal found 5/10![Frontier logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 6/212:27 pm
MDW
- MBJ
1 stop23h 44m
Frontier
Deal found 5/10![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 7/312:04 pm
MDW
- MBJ
1 stop24h 17m
Frontier
Deal found 5/9![Frontier logo]()
$233
This Mytrip deal was found by Cheapflights users on 5/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1611:59 am
MDW
- MBJ
1 stop24h 12m
Frontier
Deal found 5/9![Frontier logo]()
$236
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 May 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $372 (Frontier) |
One-way from | $148 (Southwest) |
Popular in | June |
Cheapest in | April |
Average price | $541 |
Good round-trip deal | $317 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 May 11, 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
Quickest round-trip
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 5/30
6:10 am-1:30 pm
1 stop7h 20m
Montego Bay Sangster Intl
Sat 6/6
2:30 pm-6:35 pm
Nonstop4h 05m
$469
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Mon 6/1
6:23 am-8:00 pm
1 stop13h 37m
Kingston Norman Manley
Fri 6/5
9:00 am-9:09 pm
1 stop12h 09m
$576
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 8/9
5:10 am-11:45 am
1 stop6h 35m
Montego Bay Sangster Intl
Thu 8/27
12:15 pm-9:55 pm
2 stops9h 40m
$576
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 5/24
6:40 am-2:20 pm
1 stop7h 40m
Montego Bay Sangster Intl
Thu 5/28
12:35 pm-10:45 pm
2 stops10h 10m
$592
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Thu 6/11
8:55 pm-2:55 pm
2 stops18h 00m
Montego Bay Sangster Intl
Tue 6/16
11:45 am-7:50 pm
2 stops8h 05m
$602
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
$609
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 7/25
5:05 am-1:30 pm
1 stop8h 25m
Montego Bay Sangster Intl
Wed 7/29
11:45 am-7:50 pm
2 stops8h 05m
$613
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Thu 7/30
8:50 pm-1:20 pm
2 stops16h 30m
Montego Bay Sangster Intl
Mon 8/3
3:55 pm-11:00 pm
1 stop7h 05m
$640
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 6/20
10:10 am-2:00 pm
Nonstop3h 50m
Montego Bay Sangster Intl
Mon 6/22
2:20 pm-12:40 am
1 stop10h 20m
$649
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Tue 6/9
7:35 pm-10:45 am
2 stops15h 10m
Montego Bay Sangster Intl
Fri 6/12
3:55 pm-11:00 pm
1 stop7h 05m
$655
Showing 1-10 of 41 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.
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 May 11, 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 May 11, 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.
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
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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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 May 11, 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 May 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$172 | Average$428 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$395 | Average$564 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$468 | Average$646 | FlexibilityNo cancel fee | On-time63% |