$173+ 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 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Sep 30 — Oct 71
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Jamaica with Cheapflights
1. Tell us where you want to go
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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 August 31, 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 August 31, 2026.
This Frontier deal was found by Cheapflights users on 8/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:25 am -
1 stop7h 03m
Thu 11/124:43 pm -
1 stop8h 04m
Deal found 8/27![Frontier logo]()
$422
This FlightHub deal was found by Cheapflights users on 8/26. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:42 pm -
1 stop19h 47m
Sun 11/14:43 pm -
1 stop8h 04m
Deal found 8/26![Frontier logo]()
$433
This FlightHub deal was found by Cheapflights users on 8/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:46 pm -
1 stop19h 41m
Mon 9/283:42 pm -
1 stop8h 02m
Deal found 8/27![Frontier logo]()
$438
This Frontier deal was found by Cheapflights users on 8/28. 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.
Fri 10/236:15 am -
1 stop8h 18m
Sun 10/253:48 pm -
1 stop7h 55m
Deal found 8/28![Frontier logo]()
$447
This Delta deal was found by Cheapflights users on 8/29. 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.
Sun 8/306:05 am -
1 stop9h 29m
Sat 9/51:09 pm -
1 stop9h 27m
Deal found 8/29![Delta logo]()
$453
This Justfly.com deal was found by Cheapflights users on 8/28. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:40 pm -
1 stop19h 53m
Sun 10/253:48 pm -
1 stop7h 55m
Deal found 8/28![Frontier logo]()
$458
This FlightHub deal was found by Cheapflights users on 8/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:42 pm -
1 stop19h 26m
Sun 11/84:43 pm -
1 stop8h 04m
Deal found 8/27![Frontier logo]()
$459
This FlightHub deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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.
Thu 11/126:42 pm -
1 stop19h 26m
Mon 11/164:23 pm -
1 stop26h 24m
Deal found 8/30![Frontier logo]()
$461
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/316:04 am -
1 stop6h 56m
Tue 11/33:26 pm -
1 stop8h 07m
Deal found 8/30![Delta logo]()
$462
This Justfly.com deal was found by Cheapflights users on 8/27. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:46 pm -
1 stop17h 16m
Mon 9/143:42 pm -
1 stop8h 02m
Deal found 8/27![Frontier logo]()
$464
This Justfly.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Thu 9/176:46 pm -
1 stop19h 41m
Sun 9/203:42 pm -
1 stop8h 02m
Deal found 8/31![Frontier logo]()
$465
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 12/67:00 am -
1 stop6h 45m
Wed 12/91:50 pm -
2 stops8h 40m
Deal found 8/31![Southwest logo]()
$467
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 August 31, 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 August 31, 2026.
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/316:04 am -
1 stop6h 56m
Tue 11/33:26 pm -
1 stop8h 07m
Deal found 8/30![Delta logo]()
$462
This Southwest deal was found by Cheapflights users on 8/26. 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.
Mon 12/76:00 am -
1 stop7h 25m
Thu 12/101:50 pm -
2 stops8h 40m
Deal found 8/26![Southwest logo]()
$467
This Southwest deal was found by Cheapflights users on 8/27. 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.
Wed 11/185:20 am -
1 stop6h 30m
Mon 11/233:25 pm -
1 stop8h 40m
Deal found 8/27![Southwest logo]()
$505
This Delta deal was found by Cheapflights users on 8/28. 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 11/36:04 am -
1 stop6h 56m
Tue 11/102:16 pm -
1 stop9h 38m
Deal found 8/28![Delta logo]()
$642
This Southwest deal was found by Cheapflights users on 8/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/305:25 am -
1 stop6h 25m
Sun 12/131:50 pm -
1 stop7h 45m
Deal found 8/28![Southwest logo]()
$597
This Southwest deal was found by Cheapflights users on 8/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/125:00 am -
1 stop6h 50m
Mon 10/1912:50 pm -
1 stop7h 05m
Deal found 8/28![Southwest logo]()
$650
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 1/116:25 am -
1 stop6h 45m
Sun 1/172:00 pm -
1 stop9h 50m
Deal found 8/30![Southwest logo]()
$668
This Delta deal was found by Cheapflights users on 8/28. 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 11/96:00 am -
1 stop13h 00m
Fri 11/139:00 am -
1 stop8h 18m
Deal found 8/28![Delta logo]()
$824
This Southwest deal was found by Cheapflights users on 8/26. 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.
Sun 1/35:25 am -
1 stop8h 20m
Fri 1/81:10 pm -
1 stop9h 10m
Deal found 8/26![Southwest logo]()
$671
This Delta deal was found by Cheapflights users on 8/29. 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 12/111:28 am -
1 stop7h 32m
Tue 12/89:00 am -
1 stop8h 17m
Deal found 8/29![Delta logo]()
$824
This Delta deal was found by Cheapflights users on 8/28. 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 9/276:05 am -
1 stop14h 05m
Sun 10/49:10 am -
1 stop7h 05m
Deal found 8/28![Delta logo]()
$824
This Southwest deal was found by Cheapflights users on 8/27. 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 10/119:20 pm -
2 stops14h 30m
Sun 10/1812:55 pm -
1 stop10h 45m
Deal found 8/27![Southwest logo]()
$715
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/199:29 am -
2 stops10h 41m
Sat 9/269:10 am -
2 stops9h 12m
Deal found 8/31![Delta logo]()
$829
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 1/48:10 am -
1 stop5h 35m
Sat 1/91:25 pm -
Nonstop4h 05m
Deal found 8/30![Southwest logo]()
$718
This Delta deal was found by Cheapflights users on 8/29. 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 10/79:29 am -
2 stops10h 46m
Sat 10/179:15 am -
1 stop13h 18m
Deal found 8/29![Delta logo]()
$889
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/149:29 am -
2 stops10h 46m
Wed 10/219:15 am -
1 stop13h 18m
Deal found 8/30![Delta logo]()
$889
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/126:05 am -
1 stop14h 05m
Sat 9/199:10 am -
1 stop13h 34m
Deal found 8/31![Delta logo]()
$933
This Delta deal was found by Cheapflights users on 8/28. 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 9/259:29 am -
2 stops10h 41m
Fri 10/29:10 am -
1 stop7h 05m
Deal found 8/28![Delta logo]()
$994
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/1310:48 am -
1 stop9h 22m
Sat 9/199:10 am -
1 stop13h 34m
Deal found 8/31![Delta logo]()
$1,042
Last-minute flights from Midway to JamaicaDiscover last-minute flight deals from Midway to Jamaica. Data last updated August 31, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jamaica. Data last updated August 31, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/29. 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.
Sun 8/306:05 am -
1 stop9h 29m
Sat 9/51:09 pm -
1 stop9h 27m
Deal found 8/29![Delta logo]()
$453
This FlightHub deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/411:50 am -
1 stop24h 27m
Sun 9/61:32 pm -
1 stop9h 15m
Deal found 8/31![Frontier logo]()
$504
This CheapOair deal was found by Cheapflights users on 8/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:45 am -
1 stop24h 32m
Sat 9/121:17 pm -
1 stop28h 29m
Deal found 8/29![Frontier logo]()
$525
This Justfly.com deal was found by Cheapflights users on 8/27. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:46 pm -
1 stop17h 16m
Mon 9/143:42 pm -
1 stop8h 02m
Deal found 8/27![Frontier logo]()
$464
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/126:05 am -
1 stop14h 05m
Sat 9/199:10 am -
1 stop13h 34m
Deal found 8/31![Delta logo]()
$933
This Justfly.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Thu 9/176:46 pm -
1 stop19h 41m
Sun 9/203:42 pm -
1 stop8h 02m
Deal found 8/31![Frontier logo]()
$465
This FlightHub deal was found by Cheapflights users on 8/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/191:06 pm -
2 stops25h 21m
Sat 9/261:17 pm -
1 stop28h 29m
Deal found 8/28![Frontier logo]()
$534
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 -
1 stop14h 05m
Sat 9/269:10 am -
1 stop13h 34m
Deal found 8/31![Delta logo]()
$824
This Southwest deal was found by Cheapflights users on 8/26. 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.
Mon 9/215:55 am -
2 stops7h 20m
Sun 9/272:00 pm -
1 stop8h 30m
Deal found 8/26![Southwest logo]()
$540
This FlightHub deal was found by Cheapflights users on 8/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:46 pm -
1 stop19h 41m
Mon 9/283:42 pm -
1 stop8h 02m
Deal found 8/27![Frontier logo]()
$438
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/241:00 pm -
1 stop7h 10m
Mon 9/289:10 am -
2 stops9h 23m
Deal found 8/30![Delta logo]()
$994
This Southwest deal was found by Cheapflights users on 8/27. 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.
Tue 9/296:15 am -
1 stop5h 40m
Sat 10/312:55 pm -
1 stop9h 20m
Deal found 8/27![Southwest logo]()
$462
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 August 31, 2026.
Search for one-way flight options from Midway to Jamaica. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
This Frontier deal was found by Cheapflights users on 8/28. 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.
Mon 10/126:15 am -
1 stop8h 18m
Deal found 8/28![Frontier logo]()
$173
This Frontier deal was found by Cheapflights users on 8/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:24 am -
1 stop8h 09m
Deal found 8/27![Frontier logo]()
$174
This Super.com deal was found by Cheapflights users on 8/27. 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.
Sat 10/246:15 am -
1 stop8h 18m
Deal found 8/27![Frontier logo]()
$175
This Frontier deal was found by Cheapflights users on 8/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:25 am -
1 stop8h 02m
Deal found 8/27![Frontier logo]()
$177
This FlightHub deal was found by Cheapflights users on 8/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:25 am -
1 stop8h 02m
Deal found 8/28![Frontier logo]()
$179
This FlightHub deal was found by Cheapflights users on 8/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:42 pm -
1 stop19h 47m
Deal found 8/28![Frontier logo]()
$192
This Priceline deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/116:46 pm -
1 stop17h 16m
Deal found 8/31![Frontier logo]()
$196
This Frontier deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/16:16 am -
1 stop8h 13m
Deal found 8/31![Frontier logo]()
$197
This Frontier deal was found by Cheapflights users on 8/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:25 am -
1 stop8h 02m
Deal found 8/27![Frontier logo]()
$202
This Southwest deal was found by Cheapflights users on 8/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/287:45 am -
Nonstop3h 55m
Deal found 8/28![Southwest logo]()
$203
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:49 pm -
2 stops22h 41m
Deal found 8/31![Delta logo]()
$207
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/296:44 pm -
2 stops20h 43m
Deal found 8/31![Delta logo]()
$213
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 August 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $422 (Frontier) |
One-way from | $173 (Frontier) |
Popular in | March |
Cheapest in | September |
Average price | $531 |
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 7,457,451 searches. Data last updated August 31, 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 Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Sat 10/31
6:04 am-1:00 pm
1 stop6h 56m
Montego Bay Sangster Intl
Tue 11/3
3:26 pm-10:33 pm
1 stop8h 07m
$462
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Mon 12/7
6:00 am-2:25 pm
1 stop7h 25m
Montego Bay Sangster Intl
Thu 12/10
1:50 pm-9:30 pm
2 stops8h 40m
$467
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Wed 11/18
5:20 am-12:50 pm
1 stop6h 30m
Montego Bay Sangster Intl
Mon 11/23
3:25 pm-11:05 pm
1 stop8h 40m
$505
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Mon 11/30
5:25 am-12:50 pm
1 stop6h 25m
Montego Bay Sangster Intl
Sun 12/13
1:50 pm-8:35 pm
1 stop7h 45m
$597
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Tue 11/3
6:04 am-2:00 pm
1 stop6h 56m
Montego Bay Sangster Intl
Tue 11/10
2:16 pm-10:54 pm
1 stop9h 38m
$642
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Mon 10/12
5:00 am-11:50 am
1 stop6h 50m
Montego Bay Sangster Intl
Mon 10/19
12:50 pm-7:55 pm
1 stop7h 05m
$650
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Mon 1/11
6:25 am-2:10 pm
1 stop6h 45m
Montego Bay Sangster Intl
Sun 1/17
2:00 pm-10:50 pm
1 stop9h 50m
$668
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Sun 1/3
5:25 am-2:45 pm
1 stop8h 20m
Montego Bay Sangster Intl
Fri 1/8
1:10 pm-9:20 pm
1 stop9h 10m
$671
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Sun 10/11
9:20 pm-11:50 am
2 stops14h 30m
Montego Bay Sangster Intl
Sun 10/18
12:55 pm-11:40 pm
1 stop10h 45m
$715
Quickest round-trip
ChicagoMontego Bay
MDW Chicago Midway - MBJ Montego Bay Sangster Intl
MDWMBJ
Chicago Midway
Mon 1/4
8:10 am-2:45 pm
1 stop5h 35m
Montego Bay Sangster Intl
Sat 1/9
1:25 pm-4:30 pm
Nonstop4h 05m
$718
Showing 1-10 of 38 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, December is the cheapest month in which you can book a flight from Chicago Midway Airport to Jamaica (average of $493). Flying from Chicago Midway Airport to Jamaica in March is currently the most expensive (average of $1,144). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Jamaica
Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated August 31, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andFrontier from Chicago Midway Airport to Jamaica to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
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
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Jamaica by adding a car rental and/or hotel reservation to your travel itinerary.
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 August 31, 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 7,457,451 searches. Data last updated August 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$172 | Average$552 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$395 | Average$648 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$467 | Average$653 | FlexibilityNo cancel fee | On-time63% |