$108+ Cheap flights from Midway (MDW) to Jamaica
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Apr 25 — May 21
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 March 26, 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 March 26, 2026.
This Priceline deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 5/121:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 3/25![Frontier logo]()
$308
This Frontier deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:49 pm
MDW
- MBJ
2 stops17h 23m
Frontier
Wed 5/61:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 3/25![Frontier logo]()
$318
This Priceline deal was found by Cheapflights users on 3/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/512:27 pm
MDW
- MBJ
1 stop23h 44m
Frontier
Tue 5/121:16 pm
MBJ
- MDW
2 stops24h 56m
Frontier
Deal found 3/21![Frontier logo]()
$323
This Expedia deal was found by Cheapflights users on 3/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Sat 5/161:16 pm
MBJ
- MDW
1 stop21h 56m
Frontier
Deal found 3/23![Frontier logo]()
$324
This FlightHub deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Sat 5/91:16 pm
MBJ
- MDW
1 stop21h 56m
Frontier
Deal found 3/25![Frontier logo]()
$325
This Priceline deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Thu 5/141:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 3/24![Frontier logo]()
$328
This Justfly.com deal was found by Cheapflights users on 3/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/42:15 pm
MDW
- MBJ
1 stop21h 56m
Frontier
Fri 5/81:16 pm
MBJ
- MDW
1 stop21h 48m
Frontier
Deal found 3/23![Frontier logo]()
$332
This FlightHub deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Tue 5/121:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 3/24![Frontier logo]()
$338
This FlightHub deal was found by Cheapflights users on 3/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:33 am
MDW
- MBJ
2 stops24h 39m
Frontier
Tue 5/121:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 3/21![Frontier logo]()
$341
This Expedia deal was found by Cheapflights users on 3/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Sun 5/101:16 pm
MBJ
- MDW
1 stop21h 53m
Frontier
Deal found 3/23![Frontier logo]()
$342
This Expedia deal was found by Cheapflights users on 3/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Thu 5/141:16 pm
MBJ
- MDW
1 stop21h 53m
Frontier
Deal found 3/22![Frontier logo]()
$345
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2710:41 am
MDW
- KIN
1 stop9h 19m
Delta
Thu 4/309:00 am
KIN
- MDW
1 stop7h 26m
Delta
Deal found 3/25![Delta logo]()
$556
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 March 26, 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 March 26, 2026.
This Southwest deal was found by Cheapflights users on 3/21. 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 4/147:00 am
MDW
- MBJ
1 stop6h 55m
Southwest
Thu 5/1412:15 pm
MBJ
- MDW
1 stop6h 45m
Southwest
Deal found 3/21![Southwest logo]()
$427
This Delta deal was found by Cheapflights users on 3/21. 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 4/266:00 am
MDW
- MBJ
1 stop9h 17m
Delta
Wed 4/292:10 pm
MBJ
- MDW
1 stop8h 18m
Delta
Deal found 3/21![Delta logo]()
$452
This Southwest deal was found by Cheapflights users on 3/22. 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.
Sun 4/267:35 am
MDW
- MBJ
1 stop6h 05m
Southwest
Wed 4/2912:15 pm
MBJ
- MDW
1 stop9h 10m
Southwest
Deal found 3/22![Southwest logo]()
$457
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:38 pm
MDW
- MBJ
2 stops20h 39m
Delta
Wed 5/64:32 pm
MBJ
- MDW
2 stops20h 10m
Delta
Deal found 3/25![Delta logo]()
$467
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/99:55 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Tue 5/1212:15 pm
MBJ
- MDW
2 stops10h 00m
Southwest
Deal found 3/25![Southwest logo]()
$462
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:38 pm
MDW
- MBJ
2 stops16h 49m
Delta
Tue 5/52:10 pm
MBJ
- MDW
1 stop8h 18m
Delta
Deal found 3/25![Delta logo]()
$467
This Delta deal was found by Cheapflights users on 3/21. 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 9/136:00 am
MDW
- MBJ
1 stop9h 34m
Delta
Sat 9/261:25 pm
MBJ
- MDW
1 stop8h 21m
Delta
Deal found 3/21![Delta logo]()
$479
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/105:15 am
MDW
- MBJ
1 stop9h 05m
Southwest
Sun 5/172:40 pm
MBJ
- MDW
1 stop9h 00m
Southwest
Deal found 3/25![Southwest logo]()
$505
This Southwest deal was found by Cheapflights users on 3/21. 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 7/2010:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Fri 7/241:50 pm
MBJ
- MDW
Nonstop4h 00m
Southwest
Deal found 3/21![Southwest logo]()
$513
This Delta deal was found by Cheapflights users on 3/21. 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 5/112:52 pm
MDW
- KIN
1 stop7h 08m
Delta
Wed 5/69:00 am
KIN
- MDW
1 stop7h 26m
Delta
Deal found 3/21![Delta logo]()
$556
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/247:30 am
MDW
- MBJ
1 stop6h 25m
Southwest
Fri 5/112:15 pm
MBJ
- MDW
2 stops10h 05m
Southwest
Deal found 3/25![Southwest logo]()
$518
This Delta deal was found by Cheapflights users on 3/22. 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.
Thu 5/1410:59 am
MDW
- KIN
1 stop9h 01m
Delta
Thu 5/219:00 am
KIN
- MDW
1 stop7h 12m
Delta
Deal found 3/22![Delta logo]()
$640
This Delta deal was found by Cheapflights users on 3/21. 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.
Thu 6/116:00 am
MDW
- KIN
1 stop14h 00m
Delta
Wed 6/179:00 am
KIN
- MDW
2 stops9h 31m
Delta
Deal found 3/21![Delta logo]()
$645
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
MDW
- KIN
1 stop14h 04m
Delta
Sun 8/239:00 am
KIN
- MDW
1 stop12h 46m
Delta
Deal found 3/26![Delta logo]()
$724
This Delta deal was found by Cheapflights users on 3/23. 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 4/810:45 am
MDW
- KIN
1 stop9h 15m
Delta
Tue 4/219:00 am
KIN
- MDW
2 stops8h 58m
Delta
Deal found 3/23![Delta logo]()
$863
Last-minute flights from Midway to JamaicaDiscover last-minute flight deals from Midway to Jamaica. Data last updated March 26, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jamaica. Data last updated March 26, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/272:41 pm
MDW
- MBJ
1 stop22h 17m
Frontier
Sat 4/49:11 am
MBJ
- MDW
1 stop10h 56m
Frontier
Deal found 3/25![Frontier logo]()
$456
This Southwest deal was found by Cheapflights users on 3/21. 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 4/147:00 am
MDW
- MBJ
1 stop6h 55m
Southwest
Thu 5/1412:15 pm
MBJ
- MDW
1 stop6h 45m
Southwest
Deal found 3/21![Southwest logo]()
$427
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:10 am
MDW
- MBJ
1 stop7h 20m
Southwest
Sat 4/2511:35 am
MBJ
- MDW
1 stop9h 05m
Southwest
Deal found 3/21![Southwest logo]()
$432
This Frontier deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:49 pm
MDW
- MBJ
2 stops17h 23m
Frontier
Wed 5/61:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 3/25![Frontier logo]()
$318
This Frontier deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:49 pm
MDW
- MBJ
2 stops17h 23m
Frontier
Thu 5/71:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 3/25![Frontier logo]()
$362
This Delta deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:00 am
MDW
- MBJ
1 stop9h 17m
Delta
Thu 4/302:10 pm
MBJ
- MDW
1 stop8h 18m
Delta
Deal found 3/24![Delta logo]()
$457
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
MDW
- MBJ
1 stop9h 17m
Delta
Wed 4/2912:44 pm
MBJ
- MDW
1 stop9h 44m
Delta
Deal found 3/25![Delta logo]()
$452
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
MDW
- MBJ
1 stop9h 17m
Delta
Tue 5/512:44 pm
MBJ
- MDW
1 stop9h 44m
Delta
Deal found 3/25![Delta logo]()
$462
This Kiwi.com deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:20 am
MDW
- MBJ
2 stops29h 56m
Multiple Airlines
Wed 5/61:16 pm
MBJ
- MDW
1 stop8h 46m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$402
This Kiwi.com deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:20 am
MDW
- MBJ
2 stops29h 56m
Multiple Airlines
Thu 5/71:16 pm
MBJ
- MDW
1 stop8h 46m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:20 am
MDW
- MBJ
2 stops29h 56m
Multiple Airlines
Sat 5/21:17 pm
MBJ
- MDW
1 stop8h 57m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$435
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2712:52 pm
MDW
- KIN
1 stop7h 08m
Delta
Fri 5/19:00 am
KIN
- MDW
1 stop13h 28m
Delta
Deal found 3/25![Delta logo]()
$556
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 March 26, 2026.
Search for one-way flight options from Midway to Jamaica. Find affordable one-way fares based on user searches. Data last updated March 26, 2026.
This Frontier deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 3/24![Frontier logo]()
$108
This FlightHub deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/42:15 pm
MDW
- MBJ
1 stop21h 56m
Frontier
Deal found 3/25![Frontier logo]()
$125
This Orbitz deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/92:56 pm
MDW
- MBJ
1 stop21h 46m
Frontier
Deal found 3/24![Frontier logo]()
$135
This Southwest deal was found by Cheapflights users on 3/21. 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 6/217:50 am
MDW
- MBJ
Nonstop3h 55m
Southwest
Deal found 3/21![Southwest logo]()
$138
This Southwest deal was found by Cheapflights users on 3/21. 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 4/207:30 am
MDW
- MBJ
1 stop6h 25m
Southwest
Deal found 3/21![Southwest logo]()
$142
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2310:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Deal found 3/24![Southwest logo]()
$148
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 3/23![Frontier logo]()
$152
This FlightHub deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 3/25![Frontier logo]()
$157
This Frontier deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 3/24![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:30 am
MDW
- MBJ
2 stops28h 46m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:34 pm
MDW
- MBJ
2 stops16h 42m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$168
This Priceline deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/242:15 pm
MDW
- MBJ
1 stop21h 57m
Frontier
Deal found 3/25![Frontier logo]()
$170
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 March 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $308 (Priceline) |
One-way from | $108 (Frontier) |
Popular in | June |
Cheapest in | January |
Average price | $592 |
Good round-trip deal | $317 or less |
Good one-way deal | $252 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 March 26, 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
Tue 4/14
7:00 am-1:55 pm
1 stop6h 55m
Montego Bay Sangster Intl
Thu 5/14
12:15 pm-7:00 pm
1 stop6h 45m
$427
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 4/26
6:00 am-3:17 pm
1 stop9h 17m
Montego Bay Sangster Intl
Wed 4/29
2:10 pm-10:28 pm
1 stop8h 18m
$452
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 4/26
7:35 am-1:40 pm
1 stop6h 05m
Montego Bay Sangster Intl
Wed 4/29
12:15 pm-9:25 pm
1 stop9h 10m
$457
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 5/9
9:55 am-1:45 pm
Nonstop3h 50m
Montego Bay Sangster Intl
Tue 5/12
12:15 pm-10:15 pm
2 stops10h 00m
$462
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 4/27
6:38 pm-3:17 pm
2 stops20h 39m
Montego Bay Sangster Intl
Wed 5/6
4:32 pm-12:42 pm
2 stops20h 10m
$467
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Tue 4/28
6:38 pm-11:27 am
2 stops16h 49m
Montego Bay Sangster Intl
Tue 5/5
2:10 pm-10:28 pm
1 stop8h 18m
$467
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 9/13
6:00 am-3:34 pm
1 stop9h 34m
Montego Bay Sangster Intl
Sat 9/26
1:25 pm-9:46 pm
1 stop8h 21m
$479
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 5/10
5:15 am-2:20 pm
1 stop9h 05m
Montego Bay Sangster Intl
Sun 5/17
2:40 pm-11:40 pm
1 stop9h 00m
$505
Quickest round-trip
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 7/20
10:05 am-1:55 pm
Nonstop3h 50m
Montego Bay Sangster Intl
Fri 7/24
1:50 pm-5:50 pm
Nonstop4h 00m
$513
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Fri 4/24
7:30 am-1:55 pm
1 stop6h 25m
Montego Bay Sangster Intl
Fri 5/1
12:15 pm-10:20 pm
2 stops10h 05m
$518
Showing 1-10 of 25 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 $375). Flying from Chicago Midway Airport to Jamaica in May is currently the most expensive (average of $611). 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 March 26, 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 March 26, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andFrontier from Chicago Midway Airport to Jamaica to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
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 March 26, 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 March 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$472 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$395 | Average$606 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$518 | Average$663 | FlexibilityNo cancel fee | On-time63% |