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Jamaica

$108+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
May 23 — May 301
Sat 5/23
Sat 5/30
1 adult, Economy
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Cheap flight deals from Midway to Jamaica

Cheapest flights from Midway to Jamaica
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 April 23, 2026.

This FlightHub deal was found by Cheapflights users on 4/19. 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.
Tue 5/56:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Tue 5/121:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Deal found 4/19$304
This Justfly.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/911:59 am
MDW
-
MBJ
1 stop24h 12m
Frontier
Mon 5/111:16 pm
MBJ
-
MDW
1 stop21h 53m
Frontier
Deal found 4/20$307
This Frontier deal was found by Cheapflights users on 4/20. 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 5/156:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Tue 5/191:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Deal found 4/20$308
This Southwest deal was found by Cheapflights users on 4/20. 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 7/2410:05 am
MDW
-
MBJ
Nonstop3h 50m
Southwest
Thu 7/301:50 pm
MBJ
-
MDW
Nonstop4h 00m
Southwest
Deal found 4/20$318
This Southwest deal was found by Cheapflights users on 4/22. 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 5/185:35 am
MDW
-
MBJ
1 stop6h 00m
Southwest
Sat 5/2311:35 am
MBJ
-
MDW
Nonstop4h 10m
Southwest
Deal found 4/22$322
This Southwest deal was found by Cheapflights users on 4/21. 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 4/267:35 am
MDW
-
MBJ
1 stop6h 05m
Southwest
Thu 4/302:55 pm
MBJ
-
MDW
1 stop7h 25m
Southwest
Deal found 4/21$332
This FlightHub deal was found by Cheapflights users on 4/18. 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 5/911:59 am
MDW
-
MBJ
1 stop24h 12m
Frontier
Thu 5/141:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Deal found 4/18$334
This Priceline deal was found by Cheapflights users on 4/21. 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 5/911:59 am
MDW
-
MBJ
1 stop24h 12m
Frontier
Fri 5/151:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Deal found 4/21$335
This Frontier deal was found by Cheapflights users on 4/18. 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 5/56:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Thu 5/141:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Deal found 4/18$338
This Justfly.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Mon 5/111:16 pm
MBJ
-
MDW
1 stop21h 53m
Frontier
Deal found 4/18$345
This Delta deal was found by Cheapflights users on 4/19. 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 5/296:23 am
MDW
-
KIN
1 stop13h 37m
Delta
Wed 6/39:00 am
KIN
-
MDW
1 stop12h 09m
Delta
Deal found 4/19$576
This Delta deal was found by Cheapflights users on 4/21. 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 5/196:23 am
MDW
-
KIN
1 stop13h 37m
Delta
Tue 5/269:00 am
KIN
-
MDW
1 stop12h 09m
Delta
Deal found 4/21$660

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 April 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$304
(FlightHub)

One-way from

$108
(Frontier)

Popular in

June

Cheapest in

January

Average price

$522

Good round-trip deal

$517 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
Search Deals
From Chicago Midway to Jamaica
Search Deals
One-way flight from Chicago Midway to Jamaica
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Jamaica.
Search Deals

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 April 23, 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

Price

Cheapest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 7/7

10:05 am-1:55 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Sat 7/11

2:30 pm-6:35 pm

Nonstop4h 05m

$318

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 7/5

7:50 am-11:45 am

Nonstop3h 55m

Montego Bay Sangster Intl

Sat 7/11

2:30 pm-6:35 pm

Nonstop4h 05m

$318
Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 7/20

10:05 am-1:55 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Tue 7/28

1:50 pm-5:50 pm

Nonstop4h 00m

$413

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/9

9:55 am-1:45 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Tue 5/12

12:15 pm-7:35 am

2 stops19h 20m

$447

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 8/20

7:15 am-1:15 pm

1 stop6h 00m

Montego Bay Sangster Intl

Mon 8/24

12:15 pm-9:30 pm

1 stop9h 15m

$450

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 5/4

6:38 pm-12:54 pm

2 stops18h 16m

Montego Bay Sangster Intl

Wed 5/13

2:21 pm-9:09 pm

1 stop6h 48m

$457

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 5/4

6:00 am-3:17 pm

1 stop9h 17m

Montego Bay Sangster Intl

Fri 5/15

4:59 pm-8:43 am

2 stops15h 44m

$457

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/2

7:50 am-11:45 am

Nonstop3h 55m

Montego Bay Sangster Intl

Sun 8/9

1:30 pm-9:20 pm

1 stop7h 50m

$538

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/16

5:10 am-1:30 pm

1 stop8h 20m

Montego Bay Sangster Intl

Thu 8/20

12:15 pm-9:55 pm

2 stops9h 40m

$554

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 7/30

11:05 am-8:03 pm

1 stop8h 58m

Kingston Norman Manley

Sun 8/30

9:00 am-9:46 pm

1 stop12h 46m

$576

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/19

Showing 1-10 of 28 resultsSorted by cheapest first
1
2
3

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.
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

What is the cheapest month to book a flight from Chicago Midway Airport to Jamaica?

Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Jamaica (average of $341). Flying from Chicago Midway Airport to Jamaica in May is currently the most expensive (average of $603). 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 April 23, 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.
Southwest
8.0
Very good
4,327 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,327 reviews
Southwest
8.0
Very good
4,327 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,438 reviews
Southwest
8.0
Very good
4,327 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,981 reviews
Southwest
8.0
Very good
4,327 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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.

  • How long is the flight from Chicago Midway Airport to Jamaica?

    There are many flights that can get you from Chicago Midway Airport to Jamaica in 3h 50m. Fly via Southwest or Delta to get the fastest option. Chicago Midway Airport and Jamaica are separated by a distance of 1709 mi. This flight may include one or multiple stops.

  • What are the cheapest flights from Chicago Midway Airport to Jamaica?

    On average you can expect to pay $542 for a flight from Chicago Midway Airport to Jamaica. The cheapest flight overall is $317 while the most popular route, (Chicago Midway - Montego Bay Sangster Intl) is currently priced at $318.

  • Can I find deals for flights from Midway to Jamaica that include hotel bookings?

    Yes. In addition to deals on Midway to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Jamaica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Jamaica.

  • Can I find deals for business class flights from Midway to Jamaica?

    Yes. Cheapflights offers flight deals from Midway to Jamaica by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Jamaica?

    Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Jamaica (average of $341). Flying from Chicago Midway Airport to Jamaica in May is currently the most expensive (average of $603). 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.

See more FAQs

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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 April 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$264Average$472FlexibilityNo cancel feeOn-time62%
DeltaCheapest$395Average$582FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$468Average$653FlexibilityNo cancel feeOn-time63%

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