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$118+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Jun 3 — Jun 101
Wed 6/3
Wed 6/10
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 May 4, 2026.

This Frontier deal was found by Cheapflights users on 4/29. 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 5/266:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Tue 6/21:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Deal found 4/29$338
This Frontier deal was found by Cheapflights users on 4/29. 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.
Wed 5/136:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Sun 5/171:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Deal found 4/29$348
This Frontier deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Thu 5/211:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Deal found 5/3$358
This Priceline deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Sat 6/61:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Deal found 5/1$372
This Frontier deal was found by Cheapflights users on 4/30. 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 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
Sat 7/251:32 pm
MBJ
-
MDW
1 stop8h 36m
Frontier
Deal found 4/30$406
This Priceline deal was found by Cheapflights users on 5/2. 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.
Mon 6/16:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Sat 6/61:16 pm
MBJ
-
MDW
1 stop21h 56m
Frontier
Deal found 5/2$410
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier 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
Fri 7/311:32 pm
MBJ
-
MDW
1 stop8h 36m
Frontier
Deal found 4/30$412
This Frontier deal was found by Cheapflights users on 4/29. 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 5/106:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Thu 5/141:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Deal found 4/29$413
This Frontier deal was found by Cheapflights users on 4/29. 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 5/266:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Wed 6/101:26 pm
MBJ
-
MDW
1 stop8h 45m
Frontier
Deal found 4/29$422
This Priceline deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:11 pm
MDW
-
MBJ
1 stop24h 16m
Frontier
Thu 8/201:26 pm
MBJ
-
MDW
1 stop8h 45m
Frontier
Deal found 5/1$424
This Delta deal was found by Cheapflights users on 4/30. 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.
Sat 5/236:23 am
MDW
-
KIN
1 stop13h 37m
Delta
Sat 5/309:00 am
KIN
-
MDW
1 stop12h 09m
Delta
Deal found 4/30$576
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:35 am
MDW
-
KIN
1 stop9h 29m
Delta
Sun 9/139:00 am
KIN
-
MDW
1 stop12h 46m
Delta
Deal found 4/29$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 May 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$338
(Frontier)

One-way from

$118
(Priceline)

Popular in

June

Cheapest in

January

Average price

$545

Good round-trip deal

$497 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. 4% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 4, 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

Fri 6/5

6:00 am-12:11 pm

1 stop6h 11m

Montego Bay Sangster Intl

Fri 6/12

1:26 pm-10:11 pm

1 stop8h 45m

$432

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 7/22

6:00 am-2:55 pm

1 stop8h 55m

Montego Bay Sangster Intl

Wed 7/29

1:50 pm-5:50 pm

Nonstop4h 00m

$447

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 6/2

6:00 am-11:35 am

1 stop5h 35m

Montego Bay Sangster Intl

Sat 6/6

2:30 pm-6:35 pm

Nonstop4h 05m

$470
Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 7/19

7:50 am-11:45 am

Nonstop3h 55m

Montego Bay Sangster Intl

Sun 7/26

2:30 pm-6:35 pm

Nonstop4h 05m

$471

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/9

9:55 am-1:45 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Wed 5/13

12:15 pm-7:45 pm

1 stop7h 30m

$478

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 7/21

10:05 am-1:55 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Sun 7/26

3:55 pm-11:40 pm

1 stop7h 45m

$501

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 7/24

6:00 am-3:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

Wed 7/29

2:31 pm-10:15 pm

1 stop7h 44m

$507

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/9

6:23 am-3:34 pm

1 stop9h 11m

Montego Bay Sangster Intl

Wed 5/13

1:18 pm-9:09 pm

1 stop7h 51m

$513

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 5/23

6:23 am-8:00 pm

1 stop13h 37m

Kingston Norman Manley

Sat 5/30

9:00 am-9:09 pm

1 stop12h 09m

$576

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 7/19

5:05 am-12:35 pm

1 stop7h 30m

Montego Bay Sangster Intl

Sat 7/25

11:55 am-6:20 pm

1 stop6h 25m

$610

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 39 resultsSorted by cheapest first
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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 May 4, 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
7.9
Good
4,308 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

7.9

Boarding

8.1

Entertainment

7.5

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
7.9
Good
4,308 reviews
Southwest
7.9
Good
4,308 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

7.9

Boarding

8.1

Entertainment

7.5

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
8,461 reviews
Southwest
7.9
Good
4,308 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

7.9

Boarding

8.1

Entertainment

7.5

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
5.6
Fair
2,966 reviews
Southwest
7.9
Good
4,308 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

7.9

Boarding

8.1

Entertainment

7.5

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 6h 11m. Fly via Frontier, 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 $520 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 $416.

  • 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 May 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$172Average$472FlexibilityNo cancel feeOn-time62%
DeltaCheapest$395Average$564FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$468Average$646FlexibilityNo cancel feeOn-time63%

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