$137+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KIN
Jun 28 — Jul 51
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Jamaica with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Midway to JamaicaExplore the most affordable flight options available from Midway to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 29, 2026.
Explore the most affordable flight options available from Midway to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 29, 2026.
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 8/156:05 am
MDW
- MBJ
1 stop6h 56m
Delta
Fri 8/212:26 pm
MBJ
- MDW
1 stop8h 10m
Delta
Deal found 5/27![Delta logo]()
$352
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 8/156:05 am
MDW
- MBJ
1 stop5h 39m
Delta
Wed 8/264:59 pm
MBJ
- MDW
2 stops16h 18m
Delta
Deal found 5/27![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 9/86:00 am
MDW
- MBJ
1 stop7h 04m
Delta
Sat 9/121:25 pm
MBJ
- MDW
1 stop8h 21m
Delta
Deal found 5/28![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 11/116:00 am
MDW
- MBJ
1 stop9h 35m
Delta
Wed 11/183:40 pm
MBJ
- MDW
1 stop7h 05m
Delta
Deal found 5/28![Delta logo]()
$420
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:05 am
MDW
- MBJ
1 stop9h 29m
Delta
Sat 9/261:25 pm
MBJ
- MDW
1 stop9h 00m
Delta
Deal found 5/28![Delta logo]()
$433
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 11/186:00 am
MDW
- MBJ
1 stop9h 35m
Delta
Wed 11/253:40 pm
MBJ
- MDW
1 stop7h 05m
Delta
Deal found 5/28![Delta logo]()
$440
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 8/96:05 am
MDW
- MBJ
1 stop9h 29m
Delta
Sat 8/152:26 pm
MBJ
- MDW
1 stop8h 10m
Delta
Deal found 5/28![Delta logo]()
$443
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:15 am
MDW
- MBJ
1 stop6h 00m
Southwest
Tue 8/1812:55 pm
MBJ
- MDW
2 stops10h 15m
Southwest
Deal found 5/27![Southwest logo]()
$445
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 10/186:00 am
MDW
- MBJ
1 stop9h 34m
Delta
Fri 10/231:32 pm
MBJ
- MDW
1 stop8h 13m
Delta
Deal found 5/27![Delta logo]()
$446
This Delta deal was found by Cheapflights users on 5/24. 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.
Wed 12/26:00 am
MDW
- MBJ
1 stop9h 35m
Delta
Sun 12/136:00 pm
MBJ
- MDW
1 stop16h 52m
Delta
Deal found 5/24![Delta logo]()
$452
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:10 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Sat 7/112:30 pm
MBJ
- MDW
1 stop8h 45m
Southwest
Deal found 5/27![Southwest logo]()
$456
This Delta deal was found by Cheapflights users on 5/24. 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 12/56:45 pm
MDW
- MBJ
2 stops20h 50m
Delta
Tue 12/86:00 pm
MBJ
- MDW
2 stops15h 45m
Delta
Deal found 5/24![Delta logo]()
$457
Best flights from Midway to JamaicaDiscover carefully curated flight deals from Midway to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 29, 2026.
Discover carefully curated flight deals from Midway to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 29, 2026.
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:05 am
MDW
- MBJ
1 stop5h 39m
Delta
Fri 8/282:26 pm
MBJ
- MDW
1 stop8h 10m
Delta
Deal found 5/27![Delta logo]()
$352
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:10 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Sat 7/112:30 pm
MBJ
- MDW
1 stop8h 45m
Southwest
Deal found 5/27![Southwest logo]()
$456
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 stop6h 00m
Delta
Sat 9/192:35 pm
MBJ
- MDW
1 stop7h 50m
Delta
Deal found 5/27![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:05 am
MDW
- MBJ
1 stop9h 29m
Delta
Sat 9/261:25 pm
MBJ
- MDW
1 stop9h 00m
Delta
Deal found 5/28![Delta logo]()
$433
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 11/186:00 am
MDW
- MBJ
1 stop9h 35m
Delta
Wed 11/253:40 pm
MBJ
- MDW
1 stop7h 05m
Delta
Deal found 5/27![Delta logo]()
$440
This Southwest deal was found by Cheapflights users on 5/24. 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.
Mon 8/247:50 pm
MDW
- MBJ
2 stops17h 05m
Southwest
Tue 9/111:50 am
MBJ
- MDW
2 stops10h 30m
Southwest
Deal found 5/24![Southwest logo]()
$533
This Delta deal was found by Cheapflights users on 5/24. 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.
Tue 8/186:05 am
MDW
- MBJ
1 stop5h 39m
Delta
Tue 8/252:26 pm
MBJ
- MDW
1 stop8h 10m
Delta
Deal found 5/24![Delta logo]()
$452
This Delta deal was found by Cheapflights users on 5/24. 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.
Fri 8/146:05 am
MDW
- MBJ
1 stop9h 29m
Delta
Tue 8/252:26 pm
MBJ
- MDW
1 stop8h 10m
Delta
Deal found 5/24![Delta logo]()
$452
This Delta deal was found by Cheapflights users on 5/24. 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 8/156:05 am
MDW
- MBJ
1 stop6h 56m
Delta
Thu 8/274:59 pm
MBJ
- MDW
2 stops16h 18m
Delta
Deal found 5/24![Delta logo]()
$457
This Delta deal was found by Cheapflights users on 5/24. 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.
Sun 8/166:05 am
MDW
- MBJ
1 stop5h 39m
Delta
Wed 8/264:59 pm
MBJ
- MDW
2 stops16h 18m
Delta
Deal found 5/24![Delta logo]()
$457
This Delta deal was found by Cheapflights users on 5/24. 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.
Mon 8/176:05 am
MDW
- MBJ
1 stop5h 39m
Delta
Wed 8/264:59 pm
MBJ
- MDW
2 stops16h 18m
Delta
Deal found 5/24![Delta logo]()
$457
This Delta deal was found by Cheapflights users on 5/24. 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.
Sun 10/186:00 am
MDW
- MBJ
1 stop9h 34m
Delta
Fri 10/231:32 pm
MBJ
- MDW
1 stop8h 13m
Delta
Deal found 5/24![Delta logo]()
$490
This Delta deal was found by Cheapflights users on 5/26. 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.
Tue 9/16:05 am
MDW
- KIN
1 stop14h 08m
Delta
Thu 9/179:00 am
KIN
- MDW
1 stop7h 11m
Delta
Deal found 5/26![Delta logo]()
$494
This Delta deal was found by Cheapflights users on 5/26. 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.
Tue 9/16:05 am
MDW
- KIN
1 stop14h 08m
Delta
Tue 9/159:00 am
KIN
- MDW
1 stop13h 25m
Delta
Deal found 5/26![Delta logo]()
$494
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 10/76:00 am
MDW
- KIN
1 stop13h 30m
Delta
Sat 10/179:00 am
KIN
- MDW
1 stop7h 25m
Delta
Deal found 5/29![Delta logo]()
$514
This Delta deal was found by Cheapflights users on 5/25. 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.
Fri 8/712:46 pm
MDW
- KIN
1 stop7h 27m
Delta
Fri 8/149:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 5/25![Delta logo]()
$565
This Delta deal was found by Cheapflights users on 5/26. 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.
Thu 10/11:00 pm
MDW
- KIN
1 stop6h 30m
Delta
Tue 10/69:00 am
KIN
- MDW
1 stop7h 25m
Delta
Deal found 5/26![Delta logo]()
$565
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 stop7h 27m
Delta
Deal found 5/29![Delta logo]()
$575
Last-minute flights from Midway to JamaicaDiscover last-minute flight deals from Midway to Jamaica. Data last updated May 29, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jamaica. Data last updated May 29, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 5/305:15 am
MDW
- MBJ
1 stop5h 55m
Southwest
Sat 6/62:30 pm
MBJ
- MDW
Nonstop4h 05m
Southwest
Deal found 5/27![Southwest logo]()
$472
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 6/26:23 am
MDW
- MBJ
1 stop9h 11m
Delta
Fri 6/52:22 pm
MBJ
- MDW
1 stop6h 47m
Delta
Deal found 5/28![Delta logo]()
$511
This Southwest deal was found by Cheapflights users on 5/24. 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.
Sat 6/610:10 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Tue 6/93:55 pm
MBJ
- MDW
1 stop7h 55m
Southwest
Deal found 5/24![Southwest logo]()
$478
This Southwest deal was found by Cheapflights users on 5/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/610:10 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Thu 6/112:20 pm
MBJ
- MDW
1 stop10h 20m
Southwest
Deal found 5/26![Southwest logo]()
$505
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 6/106:00 am
MDW
- KIN
1 stop14h 00m
Delta
Sat 6/139:00 am
KIN
- MDW
1 stop13h 17m
Delta
Deal found 5/27![Delta logo]()
$590
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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
1 stop7h 16m
Delta
Deal found 5/28![Delta logo]()
$524
This Priceline deal was found by Cheapflights users on 5/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/126:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Tue 6/161:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/26![Frontier logo]()
$492
This Super.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 6/136:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Tue 6/161:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/28![Frontier logo]()
$516
This Expedia deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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.
Sat 6/136:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Fri 6/191:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/28![Frontier logo]()
$532
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 6/147:50 am
MDW
- MBJ
Nonstop3h 55m
Southwest
Thu 6/1811:45 am
MBJ
- MDW
1 stop9h 40m
Southwest
Deal found 5/27![Southwest logo]()
$501
This Frontier deal was found by Cheapflights users on 5/25. 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.
Sat 6/206:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Thu 6/251:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/25![Frontier logo]()
$536
This Priceline deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Sun 7/51:39 pm
MBJ
- MDW
1 stop8h 24m
Frontier
Deal found 5/27![Frontier logo]()
$522
One-way flights from Midway to JamaicaSearch for one-way flight options from Midway to Jamaica. Find affordable one-way fares based on user searches. Data last updated May 29, 2026.
Search for one-way flight options from Midway to Jamaica. Find affordable one-way fares based on user searches. Data last updated May 29, 2026.
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 7/216:00 am
MDW
- MBJ
1 stop9h 34m
Delta
Deal found 5/28![Delta logo]()
$137
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 7/276:58 pm
MDW
- MBJ
2 stops18h 08m
Delta
Deal found 5/28![Delta logo]()
$143
This Southwest deal was found by Cheapflights users on 5/24. 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.
Sat 6/2010:10 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Deal found 5/24![Southwest logo]()
$148
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:05 am
MDW
- MBJ
1 stop5h 39m
Delta
Deal found 5/28![Delta logo]()
$152
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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
- MBJ
2 stops18h 19m
Delta
Deal found 5/28![Delta logo]()
$158
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 11/246:00 am
MDW
- MBJ
1 stop9h 35m
Delta
Deal found 5/29![Delta logo]()
$184
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 7/259:19 am
MDW
- MBJ
2 stops26h 33m
Delta
Deal found 5/28![Delta logo]()
$190
This Super.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 6/236:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Deal found 5/27![Frontier logo]()
$201
This Delta deal was found by Cheapflights users on 5/26. 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.
Sat 7/186:00 am
MDW
- MBJ
1 stop9h 34m
Delta
Deal found 5/26![Delta logo]()
$202
This Delta deal was found by Cheapflights users on 5/24. 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.
Wed 7/811:05 am
MDW
- KIN
1 stop8h 58m
Delta
Deal found 5/24![Delta logo]()
$202
This Frontier deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 7/256:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 5/28![Frontier logo]()
$222
This Delta deal was found by Cheapflights users on 5/24. 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.
Fri 6/56:23 am
MDW
- KIN
1 stop13h 37m
Delta
Deal found 5/24![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 May 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $352 (Delta) |
One-way from | $137 (Delta) |
Popular in | June |
Cheapest in | April |
Average price | $536 |
Good round-trip deal | $497 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Jamaica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 29, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Jamaica that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 8/22
6:05 am-11:44 am
1 stop5h 39m
Montego Bay Sangster Intl
Fri 8/28
2:26 pm-10:36 pm
1 stop8h 10m
$352
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 9/13
6:00 am-12:00 pm
1 stop6h 00m
Montego Bay Sangster Intl
Sat 9/19
2:35 pm-10:25 pm
1 stop7h 50m
$399
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 9/19
6:05 am-3:34 pm
1 stop9h 29m
Montego Bay Sangster Intl
Sat 9/26
1:25 pm-10:25 pm
1 stop9h 00m
$433
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Wed 11/18
6:00 am-4:35 pm
1 stop9h 35m
Montego Bay Sangster Intl
Wed 11/25
3:40 pm-9:45 pm
1 stop7h 05m
$440
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Tue 8/18
6:05 am-11:44 am
1 stop5h 39m
Montego Bay Sangster Intl
Tue 8/25
2:26 pm-10:36 pm
1 stop8h 10m
$452
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Fri 8/14
6:05 am-3:34 pm
1 stop9h 29m
Montego Bay Sangster Intl
Tue 8/25
2:26 pm-10:36 pm
1 stop8h 10m
$452
Quickest round-trip
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 7/4
10:10 am-2:00 pm
Nonstop3h 50m
Montego Bay Sangster Intl
Sat 7/11
2:30 pm-11:15 pm
1 stop8h 45m
$456
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 8/15
6:05 am-1:01 pm
1 stop6h 56m
Montego Bay Sangster Intl
Thu 8/27
4:59 pm-9:17 am
2 stops16h 18m
$457
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 8/16
6:05 am-11:44 am
1 stop5h 39m
Montego Bay Sangster Intl
Wed 8/26
4:59 pm-9:17 am
2 stops16h 18m
$457
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 8/17
6:05 am-11:44 am
1 stop5h 39m
Montego Bay Sangster Intl
Wed 8/26
4:59 pm-9:17 am
2 stops16h 18m
$457
Showing 1-10 of 36 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 November is currently the most expensive (average of $564). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to JM?
Find hourly flight availability from Midway to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 29, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Jamaica as you normally would.
Reviews of airlines servicing Jamaica
Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated May 29, 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
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
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 May 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Midway to Jamaica
Discover the top 3 airlines that operate flights from Midway to Jamaica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$172 | Average$428 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$395 | Average$564 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$468 | Average$646 | FlexibilityNo cancel fee | On-time63% |