$177+ 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Aug 22 — Aug 291
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 July 23, 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 July 23, 2026.
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:00 am
MDW
- MBJ
1 stop9h 35m
Delta
Sun 12/136:00 pm
MBJ
- MDW
1 stop16h 52m
Delta
Deal found 7/20![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:30 pm
MDW
- MBJ
2 stops18h 45m
Delta
Fri 12/112:20 pm
MBJ
- MDW
1 stop8h 50m
Delta
Deal found 7/20![Delta logo]()
$407
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:55 am
MDW
- MBJ
1 stop6h 30m
Southwest
Wed 9/2312:55 pm
MBJ
- MDW
1 stop8h 05m
Southwest
Deal found 7/22![Southwest logo]()
$442
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:55 pm
MDW
- MBJ
2 stops16h 00m
Southwest
Thu 9/242:15 pm
MBJ
- MDW
2 stops17h 15m
Southwest
Deal found 7/22![Southwest logo]()
$447
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:00 am
MDW
- MBJ
1 stop9h 35m
Delta
Wed 12/96:00 pm
MBJ
- MDW
1 stop16h 52m
Delta
Deal found 7/20![Delta logo]()
$460
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:05 am
MDW
- MBJ
1 stop7h 20m
Southwest
Wed 12/91:50 pm
MBJ
- MDW
2 stops8h 40m
Southwest
Deal found 7/20![Southwest logo]()
$465
This Southwest deal was found by Cheapflights users on 7/21. 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.
Mon 8/247:25 am
MDW
- MBJ
1 stop5h 50m
Southwest
Thu 9/32:15 pm
MBJ
- MDW
1 stop7h 15m
Southwest
Deal found 7/21![Southwest logo]()
$475
This Delta deal was found by Cheapflights users on 7/23. 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.
Tue 10/66:45 pm
MDW
- MBJ
2 stops16h 40m
Delta
Wed 10/212:45 pm
MBJ
- MDW
1 stop7h 40m
Delta
Deal found 7/23![Delta logo]()
$485
This Frontier deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sun 8/231:32 pm
MBJ
- MDW
1 stop9h 15m
Frontier
Deal found 7/19![Frontier logo]()
$492
This FlightHub deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:25 am
MDW
- MBJ
1 stop6h 06m
Frontier
Sat 9/192:49 pm
MBJ
- MDW
1 stop7h 09m
Frontier
Deal found 7/18![Frontier logo]()
$495
This Delta deal was found by Cheapflights users on 7/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:05 am
MDW
- KIN
1 stop14h 08m
Delta
Sun 8/239:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 7/21![Delta logo]()
$544
This Delta deal was found by Cheapflights users on 7/23. 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 10/46:05 am
MDW
- KIN
1 stop14h 05m
Delta
Wed 10/219:00 am
KIN
- MDW
1 stop7h 20m
Delta
Deal found 7/23![Delta logo]()
$584
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 July 23, 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 July 23, 2026.
This Southwest deal was found by Cheapflights users on 7/18. 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 9/195:55 am
MDW
- MBJ
1 stop6h 30m
Southwest
Wed 9/2312:55 pm
MBJ
- MDW
1 stop8h 05m
Southwest
Deal found 7/18![Southwest logo]()
$402
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:05 am
MDW
- KIN
1 stop14h 08m
Delta
Sun 8/239:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 7/20![Delta logo]()
$544
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:55 pm
MDW
- MBJ
2 stops16h 00m
Southwest
Thu 9/242:15 pm
MBJ
- MDW
1 stop8h 25m
Southwest
Deal found 7/22![Southwest logo]()
$447
This Delta deal was found by Cheapflights users on 7/19. 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 9/309:29 am
MDW
- KIN
2 stops10h 41m
Delta
Sun 10/49:10 am
KIN
- MDW
1 stop13h 34m
Delta
Deal found 7/19![Delta logo]()
$549
This Southwest deal was found by Cheapflights users on 7/18. 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.
Mon 8/245:00 am
MDW
- MBJ
1 stop8h 15m
Southwest
Thu 8/272:15 pm
MBJ
- MDW
2 stops8h 05m
Southwest
Deal found 7/18![Southwest logo]()
$513
This Delta deal was found by Cheapflights users on 7/18. 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 8/246:05 am
MDW
- MBJ
1 stop9h 29m
Delta
Thu 8/272:26 pm
MBJ
- MDW
1 stop8h 10m
Delta
Deal found 7/18![Delta logo]()
$556
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:25 am
MDW
- MBJ
1 stop5h 50m
Southwest
Fri 9/1112:15 pm
MBJ
- MDW
2 stops10h 10m
Southwest
Deal found 7/22![Southwest logo]()
$517
This Delta deal was found by Cheapflights users on 7/23. 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.
Fri 10/910:58 am
MDW
- KIN
1 stop8h 32m
Delta
Fri 10/239:00 am
KIN
- MDW
1 stop13h 25m
Delta
Deal found 7/23![Delta logo]()
$584
This Southwest deal was found by Cheapflights users on 7/18. 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 8/225:00 am
MDW
- MBJ
1 stop7h 50m
Southwest
Sun 8/3012:45 pm
MBJ
- MDW
2 stops9h 40m
Southwest
Deal found 7/18![Southwest logo]()
$535
This Delta deal was found by Cheapflights users on 7/23. 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.
Fri 10/910:58 am
MDW
- KIN
1 stop8h 32m
Delta
Tue 10/209:00 am
KIN
- MDW
1 stop7h 20m
Delta
Deal found 7/23![Delta logo]()
$584
This Southwest deal was found by Cheapflights users on 7/21. 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.
Sun 8/98:45 pm
MDW
- MBJ
2 stops15h 00m
Southwest
Sat 8/2912:20 pm
MBJ
- MDW
1 stop8h 35m
Southwest
Deal found 7/21![Southwest logo]()
$549
This Delta deal was found by Cheapflights users on 7/23. 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.
Wed 10/71:00 pm
MDW
- KIN
1 stop6h 30m
Delta
Wed 10/219:00 am
KIN
- MDW
2 stops9h 05m
Delta
Deal found 7/23![Delta logo]()
$589
This Delta deal was found by Cheapflights users on 7/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:05 am
MDW
- KIN
1 stop14h 08m
Delta
Sun 9/139:10 am
KIN
- MDW
1 stop13h 34m
Delta
Deal found 7/21![Delta logo]()
$590
This Southwest deal was found by Cheapflights users on 7/20. 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.
Wed 8/196:15 am
MDW
- MBJ
1 stop5h 40m
Southwest
Wed 8/2612:55 pm
MBJ
- MDW
1 stop8h 05m
Southwest
Deal found 7/20![Southwest logo]()
$603
This Delta deal was found by Cheapflights users on 7/18. 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 8/229:24 am
MDW
- KIN
2 stops10h 49m
Delta
Tue 8/259:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 7/18![Delta logo]()
$595
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:25 am
MDW
- MBJ
1 stop5h 50m
Southwest
Tue 9/1512:55 pm
MBJ
- MDW
1 stop8h 05m
Southwest
Deal found 7/20![Southwest logo]()
$627
This Delta deal was found by Cheapflights users on 7/23. 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.
Tue 10/61:00 pm
MDW
- KIN
1 stop6h 30m
Delta
Sun 10/189:00 am
KIN
- MDW
1 stop7h 20m
Delta
Deal found 7/23![Delta logo]()
$630
This Southwest deal was found by Cheapflights users on 7/23. 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 9/306:30 am
MDW
- MBJ
1 stop6h 25m
Southwest
Mon 10/512:00 pm
MBJ
- MDW
2 stops11h 10m
Southwest
Deal found 7/23![Southwest logo]()
$662
Last-minute flights from Midway to JamaicaDiscover last-minute flight deals from Midway to Jamaica. Data last updated July 23, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jamaica. Data last updated July 23, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 7/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sat 8/151:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 7/21![Frontier logo]()
$518
This Priceline deal was found by Cheapflights users on 7/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:05 am
MDW
- MBJ
1 stop6h 19m
Frontier
Fri 8/141:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 7/22![Frontier logo]()
$528
This Frontier deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sun 8/231:32 pm
MBJ
- MDW
1 stop9h 15m
Frontier
Deal found 7/19![Frontier logo]()
$492
This Southwest deal was found by Cheapflights users on 7/21. 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 8/155:55 am
MDW
- MBJ
1 stop6h 30m
Southwest
Fri 8/212:15 pm
MBJ
- MDW
1 stop8h 25m
Southwest
Deal found 7/21![Southwest logo]()
$505
This Delta deal was found by Cheapflights users on 7/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:05 am
MDW
- KIN
1 stop14h 08m
Delta
Sun 8/239:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 7/21![Delta logo]()
$544
This Southwest deal was found by Cheapflights users on 7/23. 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.
Sat 8/225:00 am
MDW
- MBJ
1 stop6h 20m
Southwest
Sat 8/2912:20 pm
MBJ
- MDW
1 stop8h 35m
Southwest
Deal found 7/23![Southwest logo]()
$442
This FlightHub deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2211:45 am
MDW
- MBJ
1 stop24h 32m
Frontier
Sun 8/301:32 pm
MBJ
- MDW
1 stop9h 15m
Frontier
Deal found 7/18![Frontier logo]()
$504
This Delta deal was found by Cheapflights users on 7/18. 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 8/226:11 am
MDW
- KIN
1 stop14h 02m
Delta
Tue 8/259:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 7/18![Delta logo]()
$590
This Southwest deal was found by Cheapflights users on 7/21. 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.
Mon 8/247:25 am
MDW
- MBJ
1 stop5h 50m
Southwest
Thu 9/32:15 pm
MBJ
- MDW
1 stop7h 15m
Southwest
Deal found 7/21![Southwest logo]()
$475
This Southwest deal was found by Cheapflights users on 7/18. 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.
Mon 8/245:55 am
MDW
- MBJ
2 stops7h 20m
Southwest
Thu 8/272:15 pm
MBJ
- MDW
2 stops8h 05m
Southwest
Deal found 7/18![Southwest logo]()
$513
This FlightHub deal was found by Cheapflights users on 7/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:50 am
MDW
- MBJ
1 stop24h 27m
Frontier
Sun 9/61:32 pm
MBJ
- MDW
1 stop9h 15m
Frontier
Deal found 7/22![Frontier logo]()
$530
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:55 pm
MDW
- MBJ
2 stops15h 25m
Southwest
Sun 9/62:00 pm
MBJ
- MDW
1 stop8h 35m
Southwest
Deal found 7/22![Southwest logo]()
$485
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 July 23, 2026.
Search for one-way flight options from Midway to Jamaica. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
This Southwest deal was found by Cheapflights users on 7/20. 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 9/195:55 am
MDW
- MBJ
1 stop6h 30m
Southwest
Deal found 7/20![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 7/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:01 pm
MDW
- MBJ
2 stops20h 34m
Delta
Deal found 7/21![Delta logo]()
$183
This Delta deal was found by Cheapflights users on 7/22. 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 9/194:30 pm
MDW
- MBJ
2 stops19h 03m
Delta
Deal found 7/22![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 7/22. 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 8/226:42 pm
MDW
- MBJ
2 stops20h 52m
Delta
Deal found 7/22![Delta logo]()
$203
This Super.com deal was found by Cheapflights users on 7/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:05 am
MDW
- MBJ
1 stop6h 19m
Frontier
Deal found 7/19![Frontier logo]()
$220
This Super.com deal was found by Cheapflights users on 7/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 7/20![Frontier logo]()
$221
This Frontier deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:40 am
MDW
- MBJ
1 stop6h 51m
Frontier
Deal found 7/19![Frontier logo]()
$222
This Justfly.com deal was found by Cheapflights users on 7/21. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 7/21![Frontier logo]()
$224
This Frontier deal was found by Cheapflights users on 7/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:25 am
MDW
- MBJ
1 stop6h 06m
Frontier
Deal found 7/22![Frontier logo]()
$227
This Delta deal was found by Cheapflights users on 7/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:00 am
MDW
- KIN
1 stop14h 03m
Delta
Deal found 7/21![Delta logo]()
$227
This FlightHub deal was found by Cheapflights users on 7/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 7/22![Frontier logo]()
$229
This Delta deal was found by Cheapflights users on 7/22. 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 8/296:11 am
MDW
- MBJ
1 stop9h 23m
Delta
Deal found 7/22![Delta logo]()
$235
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 July 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $402 (Southwest) |
One-way from | $177 (Southwest) |
Popular in | December |
Cheapest in | September |
Average price | $549 |
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 July 23, 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
Sat 9/19
5:55 am-12:25 pm
1 stop6h 30m
Montego Bay Sangster Intl
Wed 9/23
12:55 pm-9:00 pm
1 stop8h 05m
$402
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 9/21
7:55 pm-11:55 am
2 stops16h 00m
Montego Bay Sangster Intl
Thu 9/24
2:15 pm-10:40 pm
1 stop8h 25m
$447
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 8/24
5:00 am-1:15 pm
1 stop8h 15m
Montego Bay Sangster Intl
Thu 8/27
2:15 pm-10:20 pm
2 stops8h 05m
$513
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 9/7
7:25 am-1:15 pm
1 stop5h 50m
Montego Bay Sangster Intl
Fri 9/11
12:15 pm-10:25 pm
2 stops10h 10m
$517
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 8/22
5:00 am-12:50 pm
1 stop7h 50m
Montego Bay Sangster Intl
Sun 8/30
12:45 pm-10:25 pm
2 stops9h 40m
$535
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Fri 8/21
6:05 am-8:13 pm
1 stop14h 08m
Kingston Norman Manley
Sun 8/23
9:13 am-10:36 pm
1 stop13h 23m
$544
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Wed 9/30
9:29 am-8:10 pm
2 stops10h 41m
Kingston Norman Manley
Sun 10/4
9:10 am-10:44 pm
1 stop13h 34m
$549
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 8/9
8:45 pm-11:45 am
2 stops15h 00m
Montego Bay Sangster Intl
Sat 8/29
12:20 pm-8:55 pm
1 stop8h 35m
$549
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 8/24
6:05 am-3:34 pm
1 stop9h 29m
Montego Bay Sangster Intl
Thu 8/27
2:26 pm-10:36 pm
1 stop8h 10m
$556
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Fri 10/9
10:58 am-7:30 pm
1 stop8h 32m
Kingston Norman Manley
Fri 10/23
9:00 am-10:25 pm
1 stop13h 25m
$584
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, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Jamaica (average of $522). Flying from Chicago Midway Airport to Jamaica in March is currently the most expensive (average of $1,144). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Jamaica
Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated July 23, 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.
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Midway to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Midway to Jamaica
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Complete your trip
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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 July 23, 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 July 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$172 | Average$493 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$395 | Average$647 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$467 | Average$653 | FlexibilityNo cancel fee | On-time63% |