$148+ Cheap flights from Midway (MDW) to Montego Bay (MBJ)
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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Jun 15 — Jun 221
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Montego Bay with Cheapflights
1. Tell us where you want to go
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 Montego BayExplore the most affordable flight options available from Midway to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 16, 2026.
Explore the most affordable flight options available from Midway to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 16, 2026.
This deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Tue 8/251:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/12![Frontier logo]()
$372
This deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Tue 8/251:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/12![Frontier logo]()
$386
This deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Thu 8/201:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/12![Frontier logo]()
$392
This Priceline deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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.
Mon 6/16:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Wed 6/101:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/12![Frontier logo]()
$402
This deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Sat 8/221:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/12![Frontier logo]()
$406
This Trip.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Sat 7/41:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/11![Frontier logo]()
$407
This Mytrip deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/212:27 pm
MDW
- MBJ
1 stop23h 44m
Frontier
Thu 6/41:16 pm
MBJ
- MDW
1 stop21h 53m
Frontier
Deal found 5/12![Frontier logo]()
$411
This deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Thu 8/201:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/12![Frontier logo]()
$412
This Trip.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Wed 6/171:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/13![Frontier logo]()
$414
This deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Mon 8/241:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/12![Frontier logo]()
$426
This Gotogate deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Sun 8/21:32 pm
MBJ
- MDW
1 stop21h 35m
Frontier
Deal found 5/11![Frontier logo]()
$430
This deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Sun 8/231:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/12![Frontier logo]()
$432
Best flights from Midway to Montego BayDiscover carefully curated flight deals from Midway to Montego Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 16, 2026.
Discover carefully curated flight deals from Midway to Montego Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 16, 2026.
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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
Thu 8/271:09 pm
MBJ
- MDW
1 stop9h 27m
Delta
Deal found 5/15![Delta logo]()
$452
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:10 am
MDW
- MBJ
1 stop8h 20m
Southwest
Wed 8/2611:50 am
MBJ
- MDW
2 stops10h 30m
Southwest
Deal found 5/12![Southwest logo]()
$573
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 stop5h 49m
Delta
Sat 9/121:25 pm
MBJ
- MDW
1 stop8h 21m
Delta
Deal found 5/13![Delta logo]()
$452
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 9/196:00 am
MDW
- MBJ
1 stop9h 34m
Delta
Wed 9/231:25 pm
MBJ
- MDW
1 stop8h 21m
Delta
Deal found 5/12![Delta logo]()
$452
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/18:35 pm
MDW
- MBJ
2 stops17h 20m
Southwest
Wed 6/1012:35 pm
MBJ
- MDW
1 stop9h 00m
Southwest
Deal found 5/12![Southwest logo]()
$619
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 9/156:00 am
MDW
- MBJ
1 stop6h 00m
Delta
Sat 9/192:35 pm
MBJ
- MDW
1 stop7h 11m
Delta
Deal found 5/11![Delta logo]()
$513
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 5/298:35 pm
MDW
- MBJ
2 stops16h 55m
Southwest
Thu 6/42:20 pm
MBJ
- MDW
1 stop10h 20m
Southwest
Deal found 5/14![Southwest logo]()
$619
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:05 am
MDW
- MBJ
1 stop5h 39m
Delta
Mon 8/311:14 pm
MBJ
- MDW
1 stop8h 32m
Delta
Deal found 5/16![Delta logo]()
$572
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/98:05 pm
MDW
- MBJ
2 stops17h 35m
Southwest
Thu 8/132:15 pm
MBJ
- MDW
2 stops8h 05m
Southwest
Deal found 5/14![Southwest logo]()
$638
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 7/136:00 am
MDW
- MBJ
1 stop9h 34m
Delta
Fri 7/172:31 pm
MBJ
- MDW
1 stop7h 44m
Delta
Deal found 5/11![Delta logo]()
$581
Last-minute flights from Midway to Montego BayDiscover last-minute flight deals from Midway to Montego Bay. Data last updated May 16, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Montego Bay. Data last updated May 16, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 5/176:23 am
MDW
- MBJ
1 stop6h 33m
Delta
Fri 5/221:18 pm
MBJ
- MDW
1 stop7h 51m
Delta
Deal found 5/16![Delta logo]()
$452
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 5/309:55 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Sat 6/62:30 pm
MBJ
- MDW
Nonstop4h 05m
Southwest
Deal found 5/15![Southwest logo]()
$468
This Priceline deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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.
Mon 6/16:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Wed 6/101:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/12![Frontier logo]()
$402
This Mytrip deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/212:27 pm
MDW
- MBJ
1 stop23h 44m
Frontier
Thu 6/41:16 pm
MBJ
- MDW
1 stop21h 53m
Frontier
Deal found 5/12![Frontier logo]()
$411
This Priceline deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/96:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Fri 6/121:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/12![Frontier logo]()
$412
This Trip.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Wed 6/171:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/13![Frontier logo]()
$414
This Frontier deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/136:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Wed 6/171:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/14![Frontier logo]()
$460
This Priceline deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/2612:04 pm
MDW
- MBJ
1 stop24h 17m
Frontier
Thu 7/21:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/12![Frontier logo]()
$471
This Frontier deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/276:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Wed 7/11:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/11![Frontier logo]()
$456
This Trip.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Sat 7/41:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 5/11![Frontier logo]()
$407
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/296:30 am
MDW
- MBJ
1 stop6h 50m
Southwest
Sat 7/42:30 pm
MBJ
- MDW
Nonstop4h 05m
Southwest
Deal found 5/11![Southwest logo]()
$447
One-way flights from Midway to Montego BaySearch for one-way flight options from Midway to Montego Bay. Find affordable one-way fares based on user searches. Data last updated May 16, 2026.
Search for one-way flight options from Midway to Montego Bay. Find affordable one-way fares based on user searches. Data last updated May 16, 2026.
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/287:50 am
MDW
- MBJ
Nonstop3h 55m
Southwest
Deal found 5/13![Southwest logo]()
$148
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 8/116:30 am
MDW
- MBJ
1 stop6h 25m
Southwest
Deal found 5/15![Southwest logo]()
$152
This Super.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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.
Wed 6/36:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 5/12![Frontier logo]()
$161
This Frontier deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 7/46:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Deal found 5/12![Frontier logo]()
$176
This Frontier deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 7/186:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Deal found 5/12![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:00 am
MDW
- MBJ
1 stop30h 27m
Frontier
Deal found 5/13![Frontier logo]()
$194
This Priceline deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 11/712:03 pm
MDW
- MBJ
1 stop25h 21m
Frontier
Deal found 5/12![Frontier logo]()
$201
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 11/95:25 pm
MDW
- MBJ
2 stops18h 00m
Delta
Deal found 5/13![Delta logo]()
$202
This Frontier deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Deal found 5/15![Frontier logo]()
$206
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 8/86:42 pm
MDW
- MBJ
2 stops20h 52m
Delta
Deal found 5/12![Delta logo]()
$208
This Frontier deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 7/136:00 am
MDW
- MBJ
1 stop6h 27m
Frontier
Deal found 5/15![Frontier logo]()
$211
Find flight deals from Midway to Montego Bay
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Montego Bay (MBJ). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $372 |
One-way from | $148 (Southwest) |
Popular in | March |
Cheapest in | August |
Average price | $646 |
Good round-trip deal | $317 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Montego Bay 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 16, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Montego Bay that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 8/9
6:05 am-3:34 pm
1 stop9h 29m
Montego Bay Sangster Intl
Thu 8/27
1:09 pm-10:36 pm
1 stop9h 27m
$452
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Tue 9/8
6:00 am-11:49 am
1 stop5h 49m
Montego Bay Sangster Intl
Sat 9/12
1:25 pm-9:46 pm
1 stop8h 21m
$452
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 9/19
6:00 am-3:34 pm
1 stop9h 34m
Montego Bay Sangster Intl
Wed 9/23
1:25 pm-9:46 pm
1 stop8h 21m
$452
Quickest round-trip
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Tue 9/15
6:00 am-12:00 pm
1 stop6h 00m
Montego Bay Sangster Intl
Sat 9/19
2:35 pm-9:46 pm
1 stop7h 11m
$513
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Wed 8/26
6:05 am-11:44 am
1 stop5h 39m
Montego Bay Sangster Intl
Mon 8/31
1:14 pm-9:46 pm
1 stop8h 32m
$572
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 8/23
5:10 am-1:30 pm
1 stop8h 20m
Montego Bay Sangster Intl
Wed 8/26
11:50 am-10:20 pm
2 stops10h 30m
$573
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 7/13
6:00 am-3:34 pm
1 stop9h 34m
Montego Bay Sangster Intl
Fri 7/17
2:31 pm-10:15 pm
1 stop7h 44m
$581
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 6/1
8:35 pm-1:55 pm
2 stops17h 20m
Montego Bay Sangster Intl
Wed 6/10
12:35 pm-9:35 pm
1 stop9h 00m
$619
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Fri 5/29
8:35 pm-1:30 pm
2 stops16h 55m
Montego Bay Sangster Intl
Thu 6/4
2:20 pm-12:40 am
1 stop10h 20m
$619
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 8/9
8:05 pm-1:40 pm
2 stops17h 35m
Montego Bay Sangster Intl
Thu 8/13
2:15 pm-10:20 pm
2 stops8h 05m
$638
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from Midway to Montego Bay
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Montego Bay in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars |
Best time to book a flight from Midway to Montego Bay
Have a flexible travel schedule? Discover the best time to fly to Montego Bay from Midway with our price prediction graph.
MDW-MBJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Montego Bay
Reviews of airlines servicing Montego Bay
Get insights into the airlines that provide service to Montego Bay. 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 Montego Bay. Reviews last updated May 16, 2026.
Read reviews from past customers who have flown Southwest,Delta, andFrontier from Chicago Midway Airport to Montego Bay. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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Other flights to Montego Bay
Explore flights to Montego Bay departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 16, 2026.
Midway and Montego Bay flights
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Top 3 airlines flying from Midway to Montego Bay
Discover the top 3 airlines that operate flights from Midway to Montego Bay. 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 16, 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% |