$202+ 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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Jul 22 — Jul 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 June 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 June 22, 2026.
This Expedia deal was found by Cheapflights users on 6/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/236:42 pm
MDW
- MBJ
2 stops20h 52m
Delta
Thu 8/272:26 pm
MBJ
- MDW
2 stops22h 13m
Delta
Deal found 6/21![Delta logo]()
$437
This Frontier deal was found by Cheapflights users on 6/19. 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.
Tue 7/286:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Wed 8/51:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/19![Frontier logo]()
$452
This Delta deal was found by Cheapflights users on 6/18. 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 9/46:05 am
MDW
- KIN
1 stop14h 08m
Delta
Sun 9/139:00 am
KIN
- MDW
1 stop12h 46m
Delta
Deal found 6/18![Delta logo]()
$466
This Frontier deal was found by Cheapflights users on 6/21. 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.
Tue 7/146:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sat 7/181:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/21![Frontier logo]()
$472
This Booking.com deal was found by Cheapflights users on 6/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2812:11 pm
MDW
- MBJ
1 stop24h 16m
Frontier
Sun 8/21:39 pm
MBJ
- MDW
1 stop8h 24m
Frontier
Deal found 6/18![Frontier logo]()
$473
This Trip.com deal was found by Cheapflights users on 6/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Thu 7/301:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/17![Frontier logo]()
$486
This Delta deal was found by Cheapflights users on 6/19. 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 12/66:00 am
MDW
- MBJ
1 stop9h 35m
Delta
Thu 12/103:40 pm
MBJ
- MDW
1 stop7h 30m
Delta
Deal found 6/19![Delta logo]()
$488
This Frontier deal was found by Cheapflights users on 6/21. 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.
Mon 7/136:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Fri 7/171:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/21![Frontier logo]()
$492
This Southwest deal was found by Cheapflights users on 6/19. 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.
Sun 8/95:00 am
MDW
- MBJ
2 stops8h 30m
Southwest
Thu 8/1312:15 pm
MBJ
- MDW
1 stop10h 25m
Southwest
Deal found 6/19![Southwest logo]()
$493
This Trip.com deal was found by Cheapflights users on 6/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sun 8/21:39 pm
MBJ
- MDW
1 stop8h 24m
Frontier
Deal found 6/18![Frontier logo]()
$494
This Frontier deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:11 pm
MDW
- MBJ
2 stops21h 01m
Frontier
Wed 7/221:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/18![Frontier logo]()
$501
This Trip.com deal was found by Cheapflights users on 6/19. 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 Trip.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
Thu 8/131:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/19![Frontier logo]()
$505
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 June 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 June 22, 2026.
This Frontier deal was found by Cheapflights users on 6/21. 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.
Wed 7/156:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Wed 7/221:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/21![Frontier logo]()
$492
This Southwest deal was found by Cheapflights users on 6/19. 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.
Sun 8/95:00 am
MDW
- MBJ
2 stops8h 30m
Southwest
Thu 8/1312:15 pm
MBJ
- MDW
1 stop10h 25m
Southwest
Deal found 6/19![Southwest logo]()
$493
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:05 am
MDW
- KIN
1 stop14h 08m
Delta
Sun 9/139:00 am
KIN
- MDW
1 stop12h 46m
Delta
Deal found 6/20![Delta logo]()
$551
This Southwest deal was found by Cheapflights users on 6/21. 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.
Tue 9/16:15 am
MDW
- MBJ
1 stop5h 40m
Southwest
Wed 9/912:55 pm
MBJ
- MDW
2 stops8h 55m
Southwest
Deal found 6/21![Southwest logo]()
$518
This Delta deal was found by Cheapflights users on 6/18. 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.
Wed 10/2110:35 am
MDW
- KIN
1 stop8h 55m
Delta
Sun 10/259:00 am
KIN
- MDW
1 stop7h 25m
Delta
Deal found 6/18![Delta logo]()
$551
This Delta deal was found by Cheapflights users on 6/18. 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.
Thu 10/2210:35 am
MDW
- KIN
1 stop8h 55m
Delta
Mon 10/269:00 am
KIN
- MDW
1 stop13h 10m
Delta
Deal found 6/18![Delta logo]()
$551
This Southwest deal was found by Cheapflights users on 6/21. 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.
Thu 10/15:05 am
MDW
- MBJ
1 stop6h 45m
Southwest
Wed 10/2112:50 pm
MBJ
- MDW
2 stops9h 00m
Southwest
Deal found 6/21![Southwest logo]()
$555
This Delta deal was found by Cheapflights users on 6/19. 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 8/219:24 am
MDW
- KIN
2 stops10h 49m
Delta
Sun 8/239:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 6/19![Delta logo]()
$556
This Southwest deal was found by Cheapflights users on 6/18. 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 9/195:00 am
MDW
- MBJ
1 stop7h 50m
Southwest
Wed 9/2312:55 pm
MBJ
- MDW
2 stops8h 55m
Southwest
Deal found 6/18![Southwest logo]()
$558
This Southwest deal was found by Cheapflights users on 6/21. 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.
Thu 8/277:55 pm
MDW
- MBJ
2 stops17h 20m
Southwest
Tue 9/112:55 pm
MBJ
- MDW
1 stop8h 05m
Southwest
Deal found 6/21![Southwest logo]()
$565
This Southwest deal was found by Cheapflights users on 6/21. 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 7/295:10 am
MDW
- MBJ
1 stop5h 35m
Southwest
Tue 8/42:10 pm
MBJ
- MDW
1 stop6h 50m
Southwest
Deal found 6/21![Southwest logo]()
$585
This Delta deal was found by Cheapflights users on 6/18. 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.
Wed 10/79:30 am
MDW
- KIN
2 stops10h 00m
Delta
Sat 10/179:00 am
KIN
- MDW
2 stops9h 37m
Delta
Deal found 6/18![Delta logo]()
$645
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
MDW
- KIN
1 stop14h 03m
Delta
Wed 7/229:00 am
KIN
- MDW
1 stop13h 15m
Delta
Deal found 6/17![Delta logo]()
$659
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:50 pm
MDW
- MBJ
2 stops17h 10m
Southwest
Tue 10/1312:00 pm
MBJ
- MDW
2 stops9h 50m
Southwest
Deal found 6/20![Southwest logo]()
$615
This Southwest deal was found by Cheapflights users on 6/17. 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.
Mon 7/278:50 pm
MDW
- MBJ
2 stops16h 30m
Southwest
Thu 7/302:20 pm
MBJ
- MDW
1 stop10h 25m
Southwest
Deal found 6/17![Southwest logo]()
$638
This Southwest deal was found by Cheapflights users on 6/18. 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.
Sun 7/196:10 am
MDW
- MBJ
2 stops8h 45m
Southwest
Thu 7/2311:45 am
MBJ
- MDW
1 stop9h 40m
Southwest
Deal found 6/18![Southwest logo]()
$670
This Southwest deal was found by Cheapflights users on 6/17. 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.
Tue 7/147:35 pm
MDW
- MBJ
2 stops15h 10m
Southwest
Sat 7/181:40 pm
MBJ
- MDW
1 stop8h 50m
Southwest
Deal found 6/17![Southwest logo]()
$670
Last-minute flights from Midway to JamaicaDiscover last-minute flight deals from Midway to Jamaica. Data last updated June 22, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jamaica. Data last updated June 22, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 6/21. 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.
Mon 7/136:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Fri 7/171:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/21![Frontier logo]()
$492
This Frontier deal was found by Cheapflights users on 6/21. 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.
Tue 7/146:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sat 7/181:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/21![Frontier logo]()
$472
This Frontier deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Wed 7/221:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/18![Frontier logo]()
$522
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
MDW
- KIN
1 stop14h 03m
Delta
Wed 7/229:00 am
KIN
- MDW
1 stop13h 15m
Delta
Deal found 6/17![Delta logo]()
$659
This Frontier deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:11 pm
MDW
- MBJ
2 stops21h 01m
Frontier
Wed 7/221:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/18![Frontier logo]()
$501
This Frontier deal was found by Cheapflights users on 6/21. 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 7/186:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sat 7/251:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/21![Frontier logo]()
$512
This Trip.com deal was found by Cheapflights users on 6/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/196:05 am
MDW
- MBJ
1 stop6h 19m
Frontier
Thu 7/231:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/19![Frontier logo]()
$526
This Frontier deal was found by Cheapflights users on 6/19. 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.
Tue 7/286:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Wed 8/51:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/19![Frontier logo]()
$452
This Booking.com deal was found by Cheapflights users on 6/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2812:11 pm
MDW
- MBJ
1 stop24h 16m
Frontier
Sun 8/21:39 pm
MBJ
- MDW
1 stop8h 24m
Frontier
Deal found 6/18![Frontier logo]()
$473
This Trip.com deal was found by Cheapflights users on 6/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Thu 7/301:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/17![Frontier logo]()
$486
This Trip.com deal was found by Cheapflights users on 6/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sun 8/21:39 pm
MBJ
- MDW
1 stop8h 24m
Frontier
Deal found 6/18![Frontier logo]()
$494
This Frontier deal was found by Cheapflights users on 6/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/3112:11 pm
MDW
- MBJ
2 stops21h 01m
Frontier
Mon 8/31:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/17![Frontier logo]()
$521
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 June 22, 2026.
Search for one-way flight options from Midway to Jamaica. Find affordable one-way fares based on user searches. Data last updated June 22, 2026.
This Frontier deal was found by Cheapflights users on 6/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 6/20![Frontier logo]()
$202
This Southwest deal was found by Cheapflights users on 6/19. 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.
Sun 8/168:45 pm
MDW
- MBJ
2 stops15h 00m
Southwest
Deal found 6/19![Southwest logo]()
$220
This Frontier deal was found by Cheapflights users on 6/21. 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 7/186:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 6/21![Frontier logo]()
$222
This Delta deal was found by Cheapflights users on 6/21. 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 8/166:42 pm
MDW
- MBJ
2 stops20h 52m
Delta
Deal found 6/21![Delta logo]()
$226
This Trip.com deal was found by Cheapflights users on 6/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/196:05 am
MDW
- MBJ
1 stop6h 19m
Frontier
Deal found 6/18![Frontier logo]()
$227
This Delta deal was found by Cheapflights users on 6/18. 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 9/155:10 pm
MDW
- MBJ
2 stops18h 15m
Delta
Deal found 6/18![Delta logo]()
$240
This CheapOair deal was found by Cheapflights users on 6/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:45 am
MDW
- MBJ
1 stop24h 32m
Frontier
Deal found 6/21![Frontier logo]()
$242
This Delta deal was found by Cheapflights users on 6/18. 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 9/136:00 am
MDW
- MBJ
2 stops29h 25m
Delta
Deal found 6/18![Delta logo]()
$246
This Southwest deal was found by Cheapflights users on 6/21. 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 7/125:05 am
MDW
- MBJ
2 stops9h 30m
Southwest
Deal found 6/21![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 6/19. 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 8/186:05 am
MDW
- MBJ
1 stop5h 39m
Delta
Deal found 6/19![Delta logo]()
$262
This Delta deal was found by Cheapflights users on 6/21. 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.
Mon 7/206:58 pm
MDW
- MBJ
2 stops20h 36m
Delta
Deal found 6/21![Delta logo]()
$263
This Delta deal was found by Cheapflights users on 6/18. 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.
Thu 7/166:00 am
MDW
- KIN
1 stop14h 04m
Delta
Deal found 6/18![Delta logo]()
$273
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 June 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $437 (Expedia) |
One-way from | $202 (Frontier) |
Popular in | March |
Cheapest in | September |
Average price | $583 |
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 June 22, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Jamaica that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Wed 7/15
6:05 am-12:27 pm
1 stop6h 22m
Montego Bay Sangster Intl
Wed 7/22
1:32 pm-10:03 pm
1 stop8h 31m
$492
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 8/9
5:00 am-1:30 pm
2 stops8h 30m
Montego Bay Sangster Intl
Thu 8/13
12:15 pm-10:40 pm
1 stop10h 25m
$493
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Tue 9/1
6:15 am-11:55 am
1 stop5h 40m
Montego Bay Sangster Intl
Wed 9/9
12:55 pm-9:50 pm
2 stops8h 55m
$518
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Fri 9/4
6:05 am-8:13 pm
1 stop14h 08m
Kingston Norman Manley
Sun 9/13
9:00 am-9:46 pm
1 stop12h 46m
$551
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Wed 10/21
10:35 am-7:30 pm
1 stop8h 55m
Kingston Norman Manley
Sun 10/25
9:00 am-4:25 pm
1 stop7h 25m
$551
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Thu 10/22
10:35 am-7:30 pm
1 stop8h 55m
Kingston Norman Manley
Mon 10/26
9:00 am-10:10 pm
1 stop13h 10m
$551
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Thu 10/1
5:05 am-11:50 am
1 stop6h 45m
Montego Bay Sangster Intl
Wed 10/21
12:50 pm-9:50 pm
2 stops9h 00m
$555
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Fri 8/21
9:24 am-8:13 pm
2 stops10h 49m
Kingston Norman Manley
Sun 8/23
9:13 am-10:36 pm
1 stop13h 23m
$556
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 9/19
5:00 am-12:50 pm
1 stop7h 50m
Montego Bay Sangster Intl
Wed 9/23
12:55 pm-9:50 pm
2 stops8h 55m
$558
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Thu 8/27
7:55 pm-1:15 pm
2 stops17h 20m
Montego Bay Sangster Intl
Tue 9/1
12:55 pm-9:00 pm
1 stop8h 05m
$565
Showing 1-10 of 31 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, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Jamaica (average of $172). Flying from Chicago Midway Airport to Jamaica in July is currently the most expensive (average of $518). 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 June 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 June 22, 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
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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 June 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 June 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$172 | Average$552 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$445 | Average$638 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$467 | Average$653 | FlexibilityNo cancel fee | On-time63% |