$187+ 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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Aug 5 — Aug 121
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 6, 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 6, 2026.
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 11/26:00 am
MDW
- MBJ
1 stop7h 20m
Delta
Thu 11/123:40 pm
MBJ
- MDW
1 stop7h 30m
Delta
Deal found 7/2![Delta logo]()
$448
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 11/36:05 am
MDW
- MBJ
1 stop7h 20m
Southwest
Tue 11/101:50 pm
MBJ
- MDW
2 stops10h 15m
Southwest
Deal found 7/3![Southwest logo]()
$453
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/276:42 pm
MDW
- KIN
2 stops25h 31m
Delta
Thu 9/39:13 am
KIN
- MDW
2 stops9h 20m
Delta
Deal found 7/3![Delta logo]()
$457
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/1910:54 am
MDW
- KIN
1 stop9h 19m
Delta
Wed 8/269:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 7/5![Delta logo]()
$464
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/216:42 pm
MDW
- KIN
2 stops25h 31m
Delta
Fri 8/289:13 am
KIN
- MDW
2 stops24h 04m
Delta
Deal found 7/3![Delta logo]()
$469
This Frontier deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sun 8/161:39 pm
MBJ
- MDW
1 stop8h 24m
Frontier
Deal found 7/6![Frontier logo]()
$472
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 11/155:10 am
MDW
- MBJ
1 stop6h 40m
Southwest
Fri 11/201:00 pm
MBJ
- MDW
1 stop11h 05m
Southwest
Deal found 7/2![Southwest logo]()
$478
This Frontier deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:05 am
MDW
- MBJ
1 stop6h 19m
Frontier
Sun 8/231:32 pm
MBJ
- MDW
1 stop9h 15m
Frontier
Deal found 7/2![Frontier logo]()
$482
This Frontier deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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
Sat 8/221:32 pm
MBJ
- MDW
1 stop9h 15m
Frontier
Deal found 7/1![Frontier logo]()
$483
This Frontier deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 10/126:40 am
MDW
- MBJ
1 stop6h 51m
Frontier
Mon 10/262:49 pm
MBJ
- MDW
1 stop7h 09m
Frontier
Deal found 7/3![Frontier logo]()
$485
This Frontier deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 10/37:25 am
MDW
- MBJ
1 stop6h 06m
Frontier
Sat 10/102:46 pm
MBJ
- MDW
1 stop7h 12m
Frontier
Deal found 7/5![Frontier logo]()
$486
This Priceline deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:03 pm
MDW
- MBJ
1 stop25h 28m
Frontier
Sat 9/122:49 pm
MBJ
- MDW
1 stop7h 09m
Frontier
Deal found 7/3![Frontier logo]()
$491
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 6, 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 6, 2026.
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 10/311:35 am
MDW
- KIN
1 stop8h 35m
Delta
Sat 10/109:00 am
KIN
- MDW
1 stop13h 25m
Delta
Deal found 7/5![Delta logo]()
$464
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/177:25 am
MDW
- MBJ
1 stop5h 50m
Southwest
Wed 8/2612:55 pm
MBJ
- MDW
1 stop8h 05m
Southwest
Deal found 7/1![Southwest logo]()
$553
This Delta deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 9/2210:48 am
MDW
- KIN
1 stop9h 22m
Delta
Fri 9/259:10 am
KIN
- MDW
1 stop13h 35m
Delta
Deal found 7/4![Delta logo]()
$464
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/2112:46 pm
MDW
- KIN
1 stop7h 27m
Delta
Fri 8/289:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 7/3![Delta logo]()
$464
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/165:00 am
MDW
- MBJ
2 stops8h 30m
Southwest
Sun 8/2312:45 pm
MBJ
- MDW
1 stop8h 35m
Southwest
Deal found 7/2![Southwest logo]()
$558
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/256:42 pm
MDW
- KIN
2 stops25h 31m
Delta
Fri 8/289:13 am
KIN
- MDW
2 stops24h 04m
Delta
Deal found 7/3![Delta logo]()
$469
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 10/18:55 pm
MDW
- MBJ
2 stops14h 55m
Southwest
Thu 10/812:00 pm
MBJ
- MDW
2 stops11h 05m
Southwest
Deal found 7/1![Southwest logo]()
$580
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 9/86:30 am
MDW
- MBJ
1 stop6h 25m
Southwest
Sun 9/1312:45 pm
MBJ
- MDW
1 stop7h 50m
Southwest
Deal found 7/1![Southwest logo]()
$587
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/1510:56 am
MDW
- KIN
1 stop9h 17m
Delta
Sat 8/229:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 7/1![Delta logo]()
$550
This Southwest deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 8/237:10 am
MDW
- MBJ
1 stop7h 15m
Southwest
Wed 8/2612:55 pm
MBJ
- MDW
1 stop8h 05m
Southwest
Deal found 7/4![Southwest logo]()
$602
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 7/5![Delta logo]()
$555
This Southwest deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 7/5![Southwest logo]()
$602
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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
- MBJ
1 stop6h 56m
Delta
Wed 10/212:45 pm
MBJ
- MDW
1 stop7h 40m
Delta
Deal found 7/5![Delta logo]()
$562
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/176:05 am
MDW
- MBJ
1 stop9h 29m
Delta
Mon 8/242:26 pm
MBJ
- MDW
1 stop8h 10m
Delta
Deal found 7/3![Delta logo]()
$627
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 9/1011:35 am
MDW
- KIN
1 stop8h 35m
Delta
Sun 9/139:10 am
KIN
- MDW
1 stop13h 35m
Delta
Deal found 7/1![Delta logo]()
$636
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 9/412:46 pm
MDW
- KIN
1 stop7h 27m
Delta
Sun 9/139:10 am
KIN
- MDW
1 stop13h 35m
Delta
Deal found 7/5![Delta logo]()
$636
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 7/176:00 am
MDW
- KIN
1 stop14h 03m
Delta
Tue 7/219:00 am
KIN
- MDW
2 stops9h 25m
Delta
Deal found 7/1![Delta logo]()
$641
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/166:05 am
MDW
- KIN
1 stop14h 08m
Delta
Sun 8/239:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 7/2![Delta logo]()
$705
Last-minute flights from Midway to JamaicaDiscover last-minute flight deals from Midway to Jamaica. Data last updated July 6, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jamaica. Data last updated July 6, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sun 8/161:39 pm
MBJ
- MDW
1 stop8h 24m
Frontier
Deal found 7/6![Frontier logo]()
$472
This CheapOair deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/112:11 pm
MDW
- MBJ
1 stop24h 13m
Frontier
Thu 8/61:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 7/5![Frontier logo]()
$511
This Trip.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/26:05 am
MDW
- MBJ
1 stop6h 19m
Frontier
Thu 8/61:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 7/2![Frontier logo]()
$508
This Frontier deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:05 am
MDW
- MBJ
1 stop6h 19m
Frontier
Thu 8/131:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 7/2![Frontier logo]()
$492
This Frontier deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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
Sat 8/221:32 pm
MBJ
- MDW
1 stop9h 15m
Frontier
Deal found 7/1![Frontier logo]()
$483
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/165:10 am
MDW
- MBJ
1 stop8h 20m
Southwest
Thu 8/2012:15 pm
MBJ
- MDW
1 stop10h 25m
Southwest
Deal found 7/1![Southwest logo]()
$448
This Frontier deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:05 am
MDW
- MBJ
1 stop6h 19m
Frontier
Sun 8/231:32 pm
MBJ
- MDW
1 stop9h 15m
Frontier
Deal found 7/2![Frontier logo]()
$482
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/1910:54 am
MDW
- KIN
1 stop9h 19m
Delta
Wed 8/269:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 7/5![Delta logo]()
$464
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/216:42 pm
MDW
- KIN
2 stops25h 31m
Delta
Fri 8/289:13 am
KIN
- MDW
2 stops24h 04m
Delta
Deal found 7/3![Delta logo]()
$469
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 7/3![Southwest logo]()
$503
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 stop6h 56m
Delta
Thu 8/271:09 pm
MBJ
- MDW
1 stop9h 27m
Delta
Deal found 7/3![Delta logo]()
$505
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/276:42 pm
MDW
- KIN
2 stops25h 31m
Delta
Thu 9/39:13 am
KIN
- MDW
2 stops9h 20m
Delta
Deal found 7/3![Delta logo]()
$457
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 6, 2026.
Search for one-way flight options from Midway to Jamaica. Find affordable one-way fares based on user searches. Data last updated July 6, 2026.
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:05 am
MDW
- KIN
1 stop14h 08m
Delta
Deal found 7/6![Delta logo]()
$187
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/65:45 pm
MDW
- KIN
2 stops26h 28m
Delta
Deal found 7/6![Delta logo]()
$193
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 9/296:05 am
MDW
- MBJ
1 stop6h 56m
Delta
Deal found 7/2![Delta logo]()
$200
This Frontier deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 7/3![Frontier logo]()
$202
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 9/277:01 pm
MDW
- MBJ
2 stops20h 33m
Delta
Deal found 7/2![Delta logo]()
$206
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/305:00 am
MDW
- MBJ
2 stops8h 30m
Southwest
Deal found 7/2![Southwest logo]()
$210
This Frontier deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/176:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 7/3![Frontier logo]()
$218
This Super.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 7/216:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 7/1![Frontier logo]()
$219
This Super.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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.
Sat 8/16:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 7/3![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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.
Thu 10/17:25 am
MDW
- MBJ
1 stop6h 06m
Frontier
Deal found 7/2![Frontier logo]()
$222
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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
Deal found 7/2![Southwest logo]()
$230
This Super.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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.
Mon 7/206:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 7/2![Frontier logo]()
$238
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 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $448 (Delta) |
One-way from | $187 (Delta) |
Popular in | March |
Cheapest in | September |
Average price | $550 |
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 6, 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
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Sat 10/3
11:35 am-8:10 pm
1 stop8h 35m
Kingston Norman Manley
Sat 10/10
9:00 am-10:25 pm
1 stop13h 25m
$464
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Tue 9/22
10:48 am-8:10 pm
1 stop9h 22m
Kingston Norman Manley
Fri 9/25
9:10 am-10:45 pm
1 stop13h 35m
$464
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Fri 8/21
12:46 pm-8:13 pm
1 stop7h 27m
Kingston Norman Manley
Fri 8/28
9:13 am-10:36 pm
1 stop13h 23m
$464
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Tue 8/25
6:42 pm-8:13 pm
2 stops25h 31m
Kingston Norman Manley
Fri 8/28
9:13 am-9:17 am
2 stops24h 04m
$469
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Sat 8/15
10:56 am-8:13 pm
1 stop9h 17m
Kingston Norman Manley
Sat 8/22
9:13 am-10:36 pm
1 stop13h 23m
$550
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 8/17
7:25 am-1:15 pm
1 stop5h 50m
Montego Bay Sangster Intl
Wed 8/26
12:55 pm-9:00 pm
1 stop8h 05m
$553
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
$555
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 8/16
5:00 am-1:30 pm
2 stops8h 30m
Montego Bay Sangster Intl
Sun 8/23
12:45 pm-9:20 pm
1 stop8h 35m
$558
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 10/4
6:05 am-1:01 pm
1 stop6h 56m
Montego Bay Sangster Intl
Wed 10/21
2:45 pm-10:25 pm
1 stop7h 40m
$562
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Thu 10/1
8:55 pm-11:50 am
2 stops14h 55m
Montego Bay Sangster Intl
Thu 10/8
12:00 pm-11:05 pm
2 stops11h 05m
$580
Showing 1-10 of 33 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-KIN
MDW-MBJ
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-KIN
MDW-MBJ
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 July 6, 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 July 6, 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.
Boarding
8.1
Overall
7.9
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Overall
7.9
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Overall
7.9
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Overall
7.9
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
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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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 July 6, 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 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$172 | Average$493 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$445 | Average$638 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$467 | Average$653 | FlexibilityNo cancel fee | On-time63% |