$197+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Sep 4 — Sep 111
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 August 5, 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 5, 2026.
This Southwest deal was found by Cheapflights users on 7/31. 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.
Tue 9/226:30 am -
1 stop6h 25m
Tue 9/2912:55 pm -
1 stop8h 30m
Deal found 7/31![Southwest logo]()
$442
This Southwest deal was found by Cheapflights users on 7/31. 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.
Mon 9/145:55 am -
2 stops7h 20m
Wed 9/1612:55 pm -
1 stop8h 05m
Deal found 7/31![Southwest logo]()
$447
This Southwest deal was found by Cheapflights users on 7/31. 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.
Tue 9/226:30 am -
1 stop6h 25m
Fri 10/3012:50 pm -
1 stop9h 10m
Deal found 7/31![Southwest logo]()
$480
This Frontier deal was found by Cheapflights users on 7/31. 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.
Mon 9/146:25 am -
1 stop8h 02m
Mon 9/213:42 pm -
1 stop8h 02m
Deal found 7/31![Frontier logo]()
$481
This FlightHub deal was found by Cheapflights users on 7/31. 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.
Wed 11/1112:03 pm -
1 stop25h 21m
Sat 11/143:39 pm -
1 stop7h 14m
Deal found 7/31![Frontier logo]()
$483
This Frontier deal was found by Cheapflights users on 7/31. 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.
Mon 10/266:40 am -
1 stop6h 51m
Fri 10/302:39 pm -
1 stop7h 14m
Deal found 7/31![Frontier logo]()
$492
This FlightHub deal was found by Cheapflights users on 8/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:25 am -
1 stop8h 02m
Sun 10/43:42 pm -
1 stop8h 02m
Deal found 8/1![Frontier logo]()
$495
This Delta deal was found by Cheapflights users on 8/4. 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.
Mon 8/316:05 am -
1 stop6h 56m
Thu 9/101:14 pm -
2 stops19h 53m
Deal found 8/4![Delta logo]()
$500
This FlightHub deal was found by Cheapflights users on 7/31. 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.
Thu 9/176:46 pm -
1 stop19h 41m
Mon 9/213:42 pm -
1 stop8h 02m
Deal found 7/31![Frontier logo]()
$504
This Delta deal was found by Cheapflights users on 7/31. 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 10/246:04 am -
1 stop5h 47m
Wed 10/282:26 pm -
1 stop8h 07m
Deal found 7/31![Delta logo]()
$508
This FlightHub deal was found by Cheapflights users on 8/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:03 pm -
1 stop25h 21m
Mon 11/163:39 pm -
1 stop7h 14m
Deal found 8/1![Frontier logo]()
$509
This Billigflug deal was found by Cheapflights users on 8/2. 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 Billigflug is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:29 am -
2 stops10h 41m
Wed 9/309:10 am -
2 stops9h 23m
Deal found 8/2![Air France logo]()
$547
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 5, 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 5, 2026.
This Southwest deal was found by Cheapflights users on 8/3. 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 9/226:30 am -
1 stop6h 25m
Tue 9/291:55 pm -
1 stop6h 55m
Deal found 8/3![Southwest logo]()
$442
This Frontier deal was found by Cheapflights users on 8/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:40 am -
1 stop6h 51m
Thu 10/292:39 pm -
1 stop7h 14m
Deal found 8/4![Frontier logo]()
$492
This Delta deal was found by Cheapflights users on 8/3. 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.
Sat 10/316:04 am -
1 stop6h 56m
Wed 11/43:26 pm -
1 stop8h 07m
Deal found 8/3![Delta logo]()
$495
This Southwest deal was found by Cheapflights users on 8/2. 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.
Sat 9/195:55 am -
1 stop6h 30m
Wed 9/231:55 pm -
1 stop6h 55m
Deal found 8/2![Southwest logo]()
$495
This Delta deal was found by Cheapflights users on 8/3. 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 9/256:05 am -
1 stop14h 05m
Mon 9/289:10 am -
1 stop7h 05m
Deal found 8/3![Delta logo]()
$556
This Delta deal was found by Cheapflights users on 8/2. 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.
Wed 9/1610:48 am -
1 stop9h 22m
Wed 9/239:10 am -
1 stop7h 05m
Deal found 8/2![Delta logo]()
$556
This Delta deal was found by Cheapflights users on 8/4. 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.
Sat 9/1911:35 am -
1 stop8h 35m
Mon 9/219:10 am -
1 stop13h 34m
Deal found 8/4![Delta logo]()
$556
This Delta deal was found by Cheapflights users on 8/2. 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.
Thu 9/246:05 am -
1 stop14h 05m
Wed 9/309:10 am -
1 stop13h 34m
Deal found 8/2![Delta logo]()
$556
This Southwest deal was found by Cheapflights users on 8/4. 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.
Sat 10/175:00 am -
1 stop8h 05m
Sat 10/2411:55 am -
2 stops19h 30m
Deal found 8/4![Southwest logo]()
$690
This Delta deal was found by Cheapflights users on 8/4. 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.
Wed 10/76:04 am -
1 stop14h 11m
Sat 10/179:15 am -
2 stops8h 45m
Deal found 8/4![Delta logo]()
$561
This Southwest deal was found by Cheapflights users on 8/3. 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.
Fri 8/287:50 pm -
2 stops16h 35m
Mon 8/312:15 pm -
2 stops8h 05m
Deal found 8/3![Southwest logo]()
$690
This Delta deal was found by Cheapflights users on 7/31. 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 9/276:05 am -
1 stop14h 05m
Sat 10/39:10 am -
1 stop13h 34m
Deal found 7/31![Delta logo]()
$564
This Delta deal was found by Cheapflights users on 8/1. 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 10/106:04 am -
1 stop6h 56m
Wed 10/141:16 pm -
1 stop9h 17m
Deal found 8/1![Delta logo]()
$600
This Delta deal was found by Cheapflights users on 8/4. 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.
Mon 8/315:45 pm -
2 stops17h 59m
Thu 9/102:26 pm -
2 stops18h 41m
Deal found 8/4![Delta logo]()
$637
This Delta deal was found by Cheapflights users on 8/4. 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 9/16:05 am -
1 stop5h 39m
Sat 9/52:26 pm -
2 stops18h 51m
Deal found 8/4![Delta logo]()
$637
This Delta deal was found by Cheapflights users on 8/4. 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.
Mon 8/316:05 am -
1 stop6h 56m
Fri 9/42:26 pm -
1 stop8h 10m
Deal found 8/4![Delta logo]()
$685
This Delta deal was found by Cheapflights users on 7/31. 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.
Mon 8/246:05 am -
1 stop9h 29m
Thu 8/271:09 pm -
1 stop9h 27m
Deal found 7/31![Delta logo]()
$761
Last-minute flights from Midway to JamaicaDiscover last-minute flight deals from Midway to Jamaica. Data last updated August 5, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jamaica. Data last updated August 5, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 8/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:45 am -
1 stop24h 32m
Sat 9/51:32 pm -
1 stop9h 15m
Deal found 8/1![Frontier logo]()
$511
This Delta deal was found by Cheapflights users on 8/4. 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.
Mon 8/316:05 am -
1 stop6h 56m
Thu 9/101:14 pm -
2 stops19h 53m
Deal found 8/4![Delta logo]()
$500
This Southwest deal was found by Cheapflights users on 7/31. 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.
Tue 9/86:30 am -
1 stop6h 25m
Sat 9/121:50 pm -
1 stop7h 10m
Deal found 7/31![Southwest logo]()
$512
This Orbitz deal was found by Cheapflights users on 8/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:25 am -
1 stop8h 02m
Mon 9/143:42 pm -
1 stop8h 02m
Deal found 8/2![Frontier logo]()
$492
This Southwest deal was found by Cheapflights users on 7/31. 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.
Mon 9/145:55 am -
2 stops7h 20m
Wed 9/1612:55 pm -
1 stop8h 05m
Deal found 7/31![Southwest logo]()
$447
This Frontier deal was found by Cheapflights users on 7/31. 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.
Mon 9/146:25 am -
1 stop8h 02m
Mon 9/213:42 pm -
1 stop8h 02m
Deal found 7/31![Frontier logo]()
$481
This FlightHub deal was found by Cheapflights users on 7/31. 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.
Thu 9/176:46 pm -
1 stop19h 41m
Mon 9/213:42 pm -
1 stop8h 02m
Deal found 7/31![Frontier logo]()
$504
This Southwest deal was found by Cheapflights users on 8/2. 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.
Sat 9/195:55 am -
1 stop6h 30m
Wed 9/2312:55 pm -
2 stops9h 30m
Deal found 8/2![Southwest logo]()
$510
This Southwest deal was found by Cheapflights users on 7/31. 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.
Tue 9/226:30 am -
1 stop6h 25m
Tue 9/2912:55 pm -
1 stop8h 30m
Deal found 7/31![Southwest logo]()
$442
This Southwest deal was found by Cheapflights users on 7/31. 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.
Tue 9/226:30 am -
1 stop6h 25m
Fri 10/3012:50 pm -
1 stop9h 10m
Deal found 7/31![Southwest logo]()
$480
This Billigflug deal was found by Cheapflights users on 8/2. 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 Billigflug is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:29 am -
2 stops10h 41m
Wed 9/309:10 am -
2 stops9h 23m
Deal found 8/2![Air France logo]()
$547
This FlightHub deal was found by Cheapflights users on 8/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:25 am -
1 stop8h 02m
Sun 10/43:42 pm -
1 stop8h 02m
Deal found 8/1![Frontier logo]()
$495
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 5, 2026.
Search for one-way flight options from Midway to Jamaica. Find affordable one-way fares based on user searches. Data last updated August 5, 2026.
This Delta deal was found by Cheapflights users on 7/31. 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 9/295:11 pm -
2 stops18h 22m
Deal found 7/31![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 8/4. 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.
Fri 10/21:00 pm -
2 stops22h 33m
Deal found 8/4![Delta logo]()
$203
This Frontier deal was found by Cheapflights users on 8/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:25 am -
1 stop8h 02m
Deal found 8/4![Frontier logo]()
$218
This Frontier deal was found by Cheapflights users on 7/31. 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.
Fri 10/26:25 am -
1 stop8h 02m
Deal found 7/31![Frontier logo]()
$222
This FlightHub deal was found by Cheapflights users on 8/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:25 am -
1 stop8h 02m
Deal found 8/4![Frontier logo]()
$224
This Delta deal was found by Cheapflights users on 8/3. 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.
Sun 9/136:05 am -
1 stop14h 05m
Deal found 8/3![Delta logo]()
$233
This Delta deal was found by Cheapflights users on 8/1. 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 10/15:10 pm -
2 stops18h 23m
Deal found 8/1![Delta logo]()
$235
This Delta deal was found by Cheapflights users on 7/31. 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.
Mon 9/146:05 am -
1 stop14h 05m
Deal found 7/31![Delta logo]()
$237
This FlightHub deal was found by Cheapflights users on 8/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:45 am -
1 stop24h 32m
Deal found 8/1![Frontier logo]()
$238
This Delta deal was found by Cheapflights users on 7/31. 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.
Fri 8/286:42 pm -
2 stops20h 52m
Deal found 7/31![Delta logo]()
$241
This Super.com deal was found by Cheapflights users on 7/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:05 am -
1 stop6h 22m
Deal found 7/31![Frontier logo]()
$243
This Delta deal was found by Cheapflights users on 8/4. 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.
Mon 8/316:05 am -
1 stop6h 56m
Deal found 8/4![Delta logo]()
$250
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 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $442 (Southwest) |
One-way from | $197 (Delta) |
Popular in | December |
Cheapest in | September |
Average price | $534 |
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 August 5, 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
Quickest round-trip
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Tue 9/22
6:30 am-12:55 pm
1 stop6h 25m
Montego Bay Sangster Intl
Tue 9/29
1:55 pm-8:50 pm
1 stop6h 55m
$442
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 10/26
6:40 am-1:31 pm
1 stop6h 51m
Montego Bay Sangster Intl
Thu 10/29
2:39 pm-9:53 pm
1 stop7h 14m
$492
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 10/31
6:04 am-1:00 pm
1 stop6h 56m
Montego Bay Sangster Intl
Wed 11/4
3:26 pm-10:33 pm
1 stop8h 07m
$495
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 9/19
5:55 am-12:25 pm
1 stop6h 30m
Montego Bay Sangster Intl
Wed 9/23
1:55 pm-8:50 pm
1 stop6h 55m
$495
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Fri 9/25
6:05 am-8:10 pm
1 stop14h 05m
Kingston Norman Manley
Mon 9/28
9:10 am-4:15 pm
1 stop7h 05m
$556
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Wed 9/16
10:48 am-8:10 pm
1 stop9h 22m
Kingston Norman Manley
Wed 9/23
9:10 am-4:15 pm
1 stop7h 05m
$556
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Sat 9/19
11:35 am-8:10 pm
1 stop8h 35m
Kingston Norman Manley
Mon 9/21
9:10 am-10:44 pm
1 stop13h 34m
$556
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Thu 9/24
6:05 am-8:10 pm
1 stop14h 05m
Kingston Norman Manley
Wed 9/30
9:10 am-10:44 pm
1 stop13h 34m
$556
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Wed 10/7
6:04 am-8:15 pm
1 stop14h 11m
Kingston Norman Manley
Sat 10/17
9:15 am-6:00 pm
2 stops8h 45m
$561
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Sun 9/27
6:05 am-8:10 pm
1 stop14h 05m
Kingston Norman Manley
Sat 10/3
9:10 am-10:44 pm
1 stop13h 34m
$564
Showing 1-10 of 32 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 5, 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
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
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
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 5, 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 August 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$172 | Average$493 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$395 | Average$647 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$467 | Average$653 | FlexibilityNo cancel fee | On-time63% |