$171+ Cheap flights from Jamaica to Midway (MDW)
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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MDW
Mar 4 — Mar 111
1 adult, Economy
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Find cheap flights from Jamaica to Midway 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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Jamaica to Midway
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Best
Last-minute
One-way
Cheapest flights from Jamaica to MidwayExplore the most affordable flight options available from Jamaica to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.
Explore the most affordable flight options available from Jamaica to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.
This Delta deal was found by Cheapflights users on 1/30. 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 3/54:05 pm
MBJ
- MDW
1 stop18h 01m
Delta
Wed 3/116:00 am
MDW
- MBJ
1 stop9h 28m
Delta
Deal found 1/30![Delta logo]()
$306
This Delta deal was found by Cheapflights users on 1/30. 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.
Tue 3/1711:15 am
MBJ
- MDW
1 stop11h 16m
Delta
Tue 3/246:00 am
MDW
- MBJ
1 stop6h 12m
Delta
Deal found 1/30![Delta logo]()
$351
This Southwest deal was found by Cheapflights users on 1/31. 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.
Thu 2/193:10 pm
MBJ
- MDW
1 stop7h 15m
Southwest
Sun 3/87:35 am
MDW
- MBJ
1 stop6h 25m
Southwest
Deal found 1/31![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 1/30. 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.
Thu 3/51:55 pm
MBJ
- MDW
2 stops11h 10m
Southwest
Wed 3/116:30 am
MDW
- MBJ
1 stop8h 00m
Southwest
Deal found 1/30![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 1/30. 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.
Tue 3/171:00 pm
MBJ
- MDW
2 stops9h 50m
Southwest
Tue 3/246:30 am
MDW
- MBJ
1 stop8h 00m
Southwest
Deal found 1/30![Southwest logo]()
$470
This WestJet deal was found by Cheapflights users on 1/30. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/177:25 pm
MBJ
- MDW
2 stops22h 29m
WestJet
Tue 3/249:35 am
MDW
- MBJ
2 stops27h 14m
WestJet
Deal found 1/30![WestJet logo]()
$1,355
This WestJet deal was found by Cheapflights users on 1/31. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/192:55 pm
MBJ
- MDW
2 stops27h 42m
WestJet
Sun 3/89:35 am
MDW
- MBJ
2 stops27h 14m
WestJet
Deal found 1/31![WestJet logo]()
$1,850
Best flights from Jamaica to MidwayDiscover carefully curated flight deals from Jamaica to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 2, 2026.
Discover carefully curated flight deals from Jamaica to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 2, 2026.
This Delta deal was found by Cheapflights users on 1/30. 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 3/54:05 pm
MBJ
- MDW
1 stop18h 01m
Delta
Wed 3/116:00 am
MDW
- MBJ
1 stop9h 28m
Delta
Deal found 1/30![Delta logo]()
$306
This Southwest deal was found by Cheapflights users on 1/31. 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.
Thu 2/193:10 pm
MBJ
- MDW
1 stop7h 15m
Southwest
Sun 3/87:35 am
MDW
- MBJ
1 stop6h 25m
Southwest
Deal found 1/31![Southwest logo]()
$371
This Delta deal was found by Cheapflights users on 1/30. 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.
Tue 3/1711:15 am
MBJ
- MDW
1 stop11h 16m
Delta
Tue 3/246:00 am
MDW
- MBJ
1 stop6h 12m
Delta
Deal found 1/30![Delta logo]()
$351
This Southwest deal was found by Cheapflights users on 1/30. 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.
Thu 3/51:55 pm
MBJ
- MDW
2 stops11h 10m
Southwest
Wed 3/116:30 am
MDW
- MBJ
1 stop8h 00m
Southwest
Deal found 1/30![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 1/30. 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.
Tue 3/171:00 pm
MBJ
- MDW
2 stops9h 50m
Southwest
Tue 3/246:30 am
MDW
- MBJ
1 stop8h 00m
Southwest
Deal found 1/30![Southwest logo]()
$470
This WestJet deal was found by Cheapflights users on 1/30. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/177:25 pm
MBJ
- MDW
2 stops22h 29m
WestJet
Tue 3/249:35 am
MDW
- MBJ
2 stops27h 14m
WestJet
Deal found 1/30![WestJet logo]()
$1,355
This WestJet deal was found by Cheapflights users on 1/31. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/192:55 pm
MBJ
- MDW
2 stops27h 42m
WestJet
Sun 3/89:35 am
MDW
- MBJ
2 stops27h 14m
WestJet
Deal found 1/31![WestJet logo]()
$1,850
Last-minute flights from Jamaica to MidwayDiscover last-minute flight deals from Jamaica to Midway. Data last updated February 2, 2026 and is based on user searches.
Discover last-minute flight deals from Jamaica to Midway. Data last updated February 2, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 1/31. 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.
Thu 2/193:10 pm
MBJ
- MDW
1 stop7h 15m
Southwest
Sun 3/87:35 am
MDW
- MBJ
1 stop6h 25m
Southwest
Deal found 1/31![Southwest logo]()
$371
This WestJet deal was found by Cheapflights users on 1/31. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/192:55 pm
MBJ
- MDW
2 stops27h 42m
WestJet
Sun 3/89:35 am
MDW
- MBJ
2 stops27h 14m
WestJet
Deal found 1/31![WestJet logo]()
$1,850
One-way flights from Jamaica to MidwaySearch for one-way flight options from Jamaica to Midway. Find affordable one-way fares based on user searches. Data last updated February 2, 2026.
Search for one-way flight options from Jamaica to Midway. Find affordable one-way fares based on user searches. Data last updated February 2, 2026.
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/193:08 pm
MBJ
- MDW
1 stop8h 29m
Frontier
Deal found 2/2![Frontier logo]()
$171
This Super.com deal was found by Cheapflights users on 2/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2110:40 am
MBJ
- MDW
1 stop11h 53m
Frontier
Deal found 2/1![Frontier logo]()
$177
This Priceline deal was found by Cheapflights users on 2/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2812:40 pm
MBJ
- MDW
1 stop9h 59m
Frontier
Deal found 2/2![Frontier logo]()
$180
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/119:01 am
MBJ
- MDW
1 stop11h 06m
Frontier
Deal found 2/2![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2010:05 am
MBJ
- MDW
1 stop13h 20m
Frontier
Deal found 2/2![Frontier logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/251:22 pm
MBJ
- MDW
1 stop8h 57m
Frontier
Deal found 2/2![Frontier logo]()
$192
This Trip.com deal was found by Cheapflights users on 1/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:22 pm
MBJ
- MDW
1 stop8h 57m
Frontier
Deal found 1/31![Frontier logo]()
$194
This Delta deal was found by Cheapflights users on 2/2. 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 4/164:32 pm
MBJ
- MDW
2 stops16h 15m
Delta
Deal found 2/2![Delta logo]()
$200
This Delta deal was found by Cheapflights users on 2/2. 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 2/264:44 pm
MBJ
- MDW
1 stop6h 47m
Delta
Deal found 2/2![Delta logo]()
$201
Find flight deals from Jamaica to Midway
Keep the following information in mind while searching for Jamaica to Midway flight deals. Data was last updated February 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $306 (Delta) |
One-way from | $171 (Trip.com) |
Popular in | June |
Cheapest in | November |
Average price | $479 |
Cheapflights Fare Finder
Customize your flight search to find flights from Jamaica to Midway 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 February 2, 2026.
Use the filters below to find and compare flights from Jamaica to Chicago Midway Airport that are best for you.
Fly from
Jamaica
Fly to
Midway
Route
Depart
Return
Price
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Thu 3/5
4:05 pm-9:06 am
1 stop18h 01m
Chicago Midway
Wed 3/11
6:00 am-3:28 pm
1 stop9h 28m
$306
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Tue 3/17
11:15 am-10:31 pm
1 stop11h 16m
Chicago Midway
Tue 3/24
6:00 am-12:12 pm
1 stop6h 12m
$351
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Thu 2/19
3:10 pm-9:25 pm
1 stop7h 15m
Chicago Midway
Sun 3/8
7:35 am-2:00 pm
1 stop6h 25m
$371
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Thu 3/5
1:55 pm-12:05 am
2 stops11h 10m
Chicago Midway
Wed 3/11
6:30 am-2:30 pm
1 stop8h 00m
$386
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Tue 3/17
1:00 pm-10:50 pm
2 stops9h 50m
Chicago Midway
Tue 3/24
6:30 am-2:30 pm
1 stop8h 00m
$470
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Tue 3/17
7:25 pm-5:54 pm
2 stops22h 29m
Chicago Midway
Tue 3/24
9:35 am-12:49 pm
2 stops27h 14m
$1,355
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Thu 2/19
2:55 pm-5:37 pm
2 stops27h 42m
Chicago Midway
Sun 3/8
9:35 am-12:49 pm
2 stops27h 14m
$1,850
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Thu 4/30
4:32 pm-8:47 am
2 stops16h 15m
$200
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Wed 5/6
2:09 pm-10:28 pm
1 stop8h 19m
$200
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Tue 5/5
12:44 pm-10:28 pm
1 stop9h 44m
$200
Showing 1-10 of 17 results
Best time to book a flight from Jamaica to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Jamaica with our price prediction graph.
MBJ-MDW
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 Jamaica to Chicago Midway Airport
JM0-MDW
MBJ-MDW
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated February 2, 2026.
Peruse reviews from past customers who have flown with Southwest from Jamaica to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Jamaica to Midway. 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 Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Jamaica to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Top airline flying from Jamaica to Midway
Discover the top airline that operate flights from Jamaica to Midway. 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 February 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$392 | Average$536 | FlexibilityNo cancel fee | On-time63% |