$187+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Jul 17 — Jul 241
Round-trip
1 adult, Economy
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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 June 17, 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 June 17, 2026.
This Frontier deal was found by Cheapflights users on 6/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Tue 8/251:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 6/16![Frontier logo]()
$472
This CheapOair deal was found by Cheapflights users on 6/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sat 7/181:32 pm
MBJ
- MDW
1 stop21h 35m
Frontier
Deal found 6/16![Frontier logo]()
$491
This Frontier deal was found by Cheapflights users on 6/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/136:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Fri 7/171:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/16![Frontier logo]()
$492
This Trip.com deal was found by Cheapflights users on 6/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:05 am
MDW
- MBJ
1 stop6h 19m
Frontier
Sat 8/81:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/12![Frontier logo]()
$507
This Trip.com deal was found by Cheapflights users on 6/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/56:05 am
MDW
- MBJ
1 stop6h 19m
Frontier
Thu 7/91:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/14![Frontier logo]()
$508
This Priceline deal was found by Cheapflights users on 6/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/116:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sat 7/181:32 pm
MBJ
- MDW
1 stop21h 35m
Frontier
Deal found 6/15![Frontier logo]()
$511
This Frontier deal was found by Cheapflights users on 6/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/126:05 am
MDW
- MBJ
1 stop6h 19m
Frontier
Sat 7/181:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/16![Frontier logo]()
$512
This Frontier deal was found by Cheapflights users on 6/15. 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.
Fri 8/2812:04 pm
MDW
- MBJ
2 stops20h 58m
Frontier
Mon 8/311:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 6/15![Frontier logo]()
$521
This Frontier deal was found by Cheapflights users on 6/12. 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.
Tue 7/286:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Thu 7/301:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/12![Frontier logo]()
$522
This CheapOair deal was found by Cheapflights users on 6/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sun 8/91:39 pm
MBJ
- MDW
2 stops51h 12m
Frontier
Deal found 6/12![Frontier logo]()
$524
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 June 17, 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 June 17, 2026.
This Southwest deal was found by Cheapflights users on 6/12. 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 8/95:00 am
MDW
- MBJ
2 stops8h 30m
Southwest
Wed 8/1912:55 pm
MBJ
- MDW
2 stops10h 15m
Southwest
Deal found 6/12![Southwest logo]()
$533
This Priceline deal was found by Cheapflights users on 6/16. 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 Priceline 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
Fri 7/31:26 pm
MBJ
- MDW
1 stop8h 45m
Frontier
Deal found 6/16![Frontier logo]()
$612
This Southwest deal was found by Cheapflights users on 6/15. 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 7/118:10 pm
MDW
- MBJ
2 stops18h 25m
Southwest
Sat 7/181:40 pm
MBJ
- MDW
1 stop8h 50m
Southwest
Deal found 6/15![Southwest logo]()
$617
This Southwest deal was found by Cheapflights users on 6/13. 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 7/196:10 am
MDW
- MBJ
2 stops8h 45m
Southwest
Sun 7/263:35 pm
MBJ
- MDW
1 stop8h 15m
Southwest
Deal found 6/13![Southwest logo]()
$637
This Southwest deal was found by Cheapflights users on 6/15. 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.
Fri 8/77:55 pm
MDW
- MBJ
2 stops15h 25m
Southwest
Mon 8/1712:15 pm
MBJ
- MDW
2 stops9h 40m
Southwest
Deal found 6/15![Southwest logo]()
$640
This Southwest deal was found by Cheapflights users on 6/12. 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.
Thu 7/308:50 pm
MDW
- MBJ
2 stops16h 30m
Southwest
Thu 8/62:15 pm
MBJ
- MDW
1 stop8h 25m
Southwest
Deal found 6/12![Southwest logo]()
$685
This Southwest deal was found by Cheapflights users on 6/13. 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.
Mon 6/296:35 pm
MDW
- MBJ
2 stops17h 00m
Southwest
Fri 7/1011:45 am
MBJ
- MDW
2 stops10h 15m
Southwest
Deal found 6/13![Southwest logo]()
$707
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:50 pm
MDW
- MBJ
2 stops16h 30m
Southwest
Thu 8/132:15 pm
MBJ
- MDW
2 stops8h 05m
Southwest
Deal found 6/16![Southwest logo]()
$713
This Southwest deal was found by Cheapflights users on 6/12. 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 6/287:50 am
MDW
- MBJ
Nonstop3h 55m
Southwest
Wed 7/13:55 pm
MBJ
- MDW
1 stop7h 55m
Southwest
Deal found 6/12![Southwest logo]()
$723
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/196:10 am
MDW
- MBJ
2 stops8h 45m
Southwest
Thu 7/2311:45 am
MBJ
- MDW
2 stops9h 30m
Southwest
Deal found 6/16![Southwest logo]()
$727
Last-minute flights from Midway to Montego BayDiscover last-minute flight deals from Midway to Montego Bay. Data last updated June 17, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Montego Bay. Data last updated June 17, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 6/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/56:05 am
MDW
- MBJ
1 stop6h 19m
Frontier
Thu 7/91:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/14![Frontier logo]()
$508
This Trip.com deal was found by Cheapflights users on 6/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sat 7/111:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/15![Frontier logo]()
$527
This Priceline deal was found by Cheapflights users on 6/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/116:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sat 7/181:32 pm
MBJ
- MDW
1 stop21h 35m
Frontier
Deal found 6/15![Frontier logo]()
$511
This Frontier deal was found by Cheapflights users on 6/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/126:05 am
MDW
- MBJ
1 stop6h 19m
Frontier
Sat 7/181:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/16![Frontier logo]()
$512
This Frontier deal was found by Cheapflights users on 6/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/136:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Fri 7/171:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/16![Frontier logo]()
$492
This CheapOair deal was found by Cheapflights users on 6/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sat 7/181:32 pm
MBJ
- MDW
1 stop21h 35m
Frontier
Deal found 6/16![Frontier logo]()
$491
This Trip.com deal was found by Cheapflights users on 6/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sat 7/251:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/15![Frontier logo]()
$507
This Frontier deal was found by Cheapflights users on 6/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:11 pm
MDW
- MBJ
2 stops21h 01m
Frontier
Fri 7/241:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/16![Frontier logo]()
$521
This CheapOair deal was found by Cheapflights users on 6/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Sun 8/91:39 pm
MBJ
- MDW
2 stops51h 12m
Frontier
Deal found 6/12![Frontier logo]()
$524
This Expedia deal was found by Cheapflights users on 6/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Mon 8/31:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/12![Frontier logo]()
$472
This Frontier deal was found by Cheapflights users on 6/12. 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.
Tue 7/286:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Thu 7/301:32 pm
MBJ
- MDW
1 stop8h 31m
Frontier
Deal found 6/12![Frontier logo]()
$522
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 June 17, 2026.
Search for one-way flight options from Midway to Montego Bay. Find affordable one-way fares based on user searches. Data last updated June 17, 2026.
This Delta deal was found by Cheapflights users on 6/12. 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.
Mon 8/246:05 am
MDW
- MBJ
1 stop9h 29m
Delta
Deal found 6/12![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 6/12. 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 8/317:50 pm
MDW
- MBJ
2 stops17h 05m
Southwest
Deal found 6/12![Southwest logo]()
$193
This Super.com deal was found by Cheapflights users on 6/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 6/15![Frontier logo]()
$201
This Frontier deal was found by Cheapflights users on 6/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 6/16![Frontier logo]()
$202
This Super.com deal was found by Cheapflights users on 6/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/136:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 6/16![Frontier logo]()
$221
This Frontier deal was found by Cheapflights users on 6/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 6/16![Frontier logo]()
$222
This Trip.com deal was found by Cheapflights users on 6/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/196:05 am
MDW
- MBJ
1 stop6h 19m
Frontier
Deal found 6/16![Frontier logo]()
$227
This Trip.com deal was found by Cheapflights users on 6/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/206:05 am
MDW
- MBJ
1 stop6h 22m
Frontier
Deal found 6/12![Frontier logo]()
$228
This Delta deal was found by Cheapflights users on 6/15. 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.
Wed 9/94:30 pm
MDW
- MBJ
2 stops19h 04m
Delta
Deal found 6/15![Delta logo]()
$240
This Frontier deal was found by Cheapflights users on 6/14. 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.
Sun 6/286:00 am
MDW
- MBJ
1 stop6h 21m
Frontier
Deal found 6/14![Frontier logo]()
$242
This Delta deal was found by Cheapflights users on 6/15. 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.
Mon 8/101:27 pm
MDW
- MBJ
2 stops22h 17m
Delta
Deal found 6/15![Delta logo]()
$246
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 June 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $452 (Frontier) |
One-way from | $187 (Delta) |
Popular in | March |
Cheapest in | April |
Average price | $672 |
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 June 17, 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
5:00 am-1:30 pm
2 stops8h 30m
Montego Bay Sangster Intl
Wed 8/19
12:55 pm-11:10 pm
2 stops10h 15m
$533
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 6/29
6:00 am-12:21 pm
1 stop6h 21m
Montego Bay Sangster Intl
Fri 7/3
1:26 pm-10:11 pm
1 stop8h 45m
$612
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 7/11
8:10 pm-2:35 pm
2 stops18h 25m
Montego Bay Sangster Intl
Sat 7/18
1:40 pm-10:30 pm
1 stop8h 50m
$617
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 7/19
6:10 am-2:55 pm
2 stops8h 45m
Montego Bay Sangster Intl
Sun 7/26
3:35 pm-11:50 pm
1 stop8h 15m
$637
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Fri 8/7
7:55 pm-11:20 am
2 stops15h 25m
Montego Bay Sangster Intl
Mon 8/17
12:15 pm-9:55 pm
2 stops9h 40m
$640
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Thu 7/30
8:50 pm-1:20 pm
2 stops16h 30m
Montego Bay Sangster Intl
Thu 8/6
2:15 pm-10:40 pm
1 stop8h 25m
$685
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 6/29
6:35 pm-11:35 am
2 stops17h 00m
Montego Bay Sangster Intl
Fri 7/10
11:45 am-10:00 pm
2 stops10h 15m
$707
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Thu 7/23
8:50 pm-1:20 pm
2 stops16h 30m
Montego Bay Sangster Intl
Thu 8/13
2:15 pm-10:20 pm
2 stops8h 05m
$713
Quickest round-trip
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 6/28
7:50 am-11:45 am
Nonstop3h 55m
Montego Bay Sangster Intl
Wed 7/1
3:55 pm-11:50 pm
1 stop7h 55m
$723
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 7/19
6:10 am-2:55 pm
2 stops8h 45m
Montego Bay Sangster Intl
Thu 7/23
11:45 am-9:15 pm
2 stops9h 30m
$727
Showing 1-10 of 20 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 June.
| 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 Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Montego Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Montego Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Montego Bay flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Montego Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Montego Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
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
What is the cheapest month to book a flight from Chicago Midway Airport to Montego Bay?
Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Montego Bay (average of $522). Flying from Chicago Midway Airport to Montego Bay 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.
What is the cheapest time of day to fly from MDW to MBJ?
Find hourly flight availability from Midway to Montego Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 17, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Montego Bay as you normally would.
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 June 17, 2026.
Read reviews from past customers who have flown Southwest and Frontier 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.
Overall
7.9
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Overall
7.9
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Overall
7.9
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from Midway to Montego Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Montego Bay?
Book flights to Montego Bay if you plan to visit one of these locationsLucea
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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 June 17, 2026.
Midway and Montego Bay flights
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Top 2 airlines flying from Midway to Montego Bay
Discover the top 2 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 June 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$172 | Average$552 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$467 | Average$653 | FlexibilityNo cancel fee | On-time63% |