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Jamaica

$123+ 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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
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 December 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:12 amMDW - MBJ
1 stop25h 47mFrontier
Thu 12/253:47 pmMBJ - MDW
1 stop7h 25mFrontier
Deal found 12/3$350
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:12 amMDW - MBJ
1 stop25h 47mMultiple Airlines
Wed 12/243:05 pmMBJ - MDW
1 stop7h 53mMultiple Airlines
Deal found 12/3$354
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:12 amMDW - MBJ
1 stop25h 47mFrontier
Wed 12/243:49 pmMBJ - MDW
1 stop7h 23mFrontier
Deal found 12/3$361
This Priceline deal was found by Cheapflights users on 12/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:15 amMDW - MBJ
1 stop6h 57mFrontier
Mon 12/223:47 pmMBJ - MDW
1 stop7h 25mFrontier
Deal found 12/3$362
This Frontier deal was found by Cheapflights users on 12/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:00 amMDW - MBJ
1 stop8h 51mFrontier
Sat 12/203:34 pmMBJ - MDW
1 stop7h 38mFrontier
Deal found 12/1$363
This Mytrip deal was found by Cheapflights users on 12/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:42 pmMDW - MBJ
1 stop18h 09mFrontier
Sat 1/104:36 pmMBJ - MDW
1 stop19h 55mFrontier
Deal found 12/2$366
This Mytrip deal was found by Cheapflights users on 12/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:12 amMDW - MBJ
1 stop7h 17mFrontier
Tue 12/303:47 pmMBJ - MDW
1 stop22h 34mFrontier
Deal found 12/2$367
This Frontier deal was found by Cheapflights users on 12/3. 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 12/226:12 amMDW - MBJ
1 stop7h 17mFrontier
Fri 12/263:47 pmMBJ - MDW
1 stop7h 25mFrontier
Deal found 12/3$387
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Thu 12/256:12 amMDW - MBJ
1 stop7h 17mFrontier
Wed 12/313:49 pmMBJ - MDW
1 stop7h 23mFrontier
Deal found 12/2$391
This Frontier deal was found by Cheapflights users on 12/3. 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.
Wed 12/246:12 amMDW - MBJ
1 stop7h 17mFrontier
Mon 12/293:47 pmMBJ - MDW
1 stop7h 25mFrontier
Deal found 12/3$393
This Mytrip deal was found by Cheapflights users on 12/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:15 amMDW - MBJ
1 stop6h 57mFrontier
Sun 12/214:16 pmMBJ - MDW
1 stop22h 05mFrontier
Deal found 12/2$407
This Delta deal was found by Cheapflights users on 12/4. 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 12/1012:50 pmMDW - KIN
1 stop6h 16mDelta
Tue 12/169:00 amKIN - MDW
1 stop8h 44mDelta
Deal found 12/4$766

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 December 4, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$350
(Kiwi.com)

One-way from

$123
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$651

Good round-trip deal

$574 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. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 4, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Jamaica that are best for you.

Fly from

Midway

Fly to

Jamaica

Route

Depart

Return

Price

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 1/6

6:50 am-2:10 pm

1 stop6h 20m

Montego Bay Sangster Intl

Sat 1/10

2:15 pm-5:35 pm

Nonstop4h 20m

$411

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 1/27

6:00 am-3:20 pm

1 stop8h 20m

Montego Bay Sangster Intl

Sat 1/31

4:45 pm-10:22 pm

1 stop6h 37m

$421

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 1/22

6:50 am-2:10 pm

1 stop6h 20m

Montego Bay Sangster Intl

Tue 1/27

2:00 pm-9:00 pm

1 stop8h 00m

$421

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 1/30

6:00 am-12:54 pm

1 stop5h 54m

Montego Bay Sangster Intl

Thu 2/5

12:38 pm-10:22 pm

1 stop10h 44m

$421

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 1/22

6:00 am-8:00 pm

1 stop13h 00m

Kingston Norman Manley

Thu 1/29

9:00 am-10:22 pm

1 stop14h 22m

$445

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 1/23

6:00 am-8:00 pm

1 stop13h 00m

Kingston Norman Manley

Sat 1/31

9:00 am-10:22 pm

1 stop14h 22m

$445

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 2/11

6:50 am-2:10 pm

1 stop6h 20m

Montego Bay Sangster Intl

Wed 2/25

2:00 pm-10:05 pm

2 stops9h 05m

$452

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 1/15

5:30 am-1:00 pm

1 stop6h 30m

Montego Bay Sangster Intl

Thu 1/22

2:00 pm-9:00 pm

1 stop8h 00m

$461

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 3/1

6:40 am-2:10 pm

1 stop6h 30m

Montego Bay Sangster Intl

Sun 3/8

12:30 pm-4:50 pm

Nonstop4h 20m

$464

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 2/7

6:40 am-3:00 pm

1 stop7h 20m

Montego Bay Sangster Intl

Sat 2/14

2:15 pm-5:35 pm

Nonstop4h 20m

$465

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 33 results
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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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Jamaica (average of $384). Flying from Chicago Midway Airport to Jamaica in March is currently the most expensive (average of $594). 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 JM?

Find hourly flight availability from Midway to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 4, 2025.

One of the essential ways to save on airfare from Chicago Midway Airport to Jamaica is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 43% on airfare.

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 December 4, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Frontier 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
4,254 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,011 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,092 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 20m. 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 $802 for a flight from Chicago Midway Airport to Jamaica. The cheapest flight overall is $485 while the most popular route, (Chicago Midway - Montego Bay Sangster Intl) is currently priced at $361.

  • 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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Jamaica (average of $384). Flying from Chicago Midway Airport to Jamaica in March is currently the most expensive (average of $594). 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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Alternative routes for Midway to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
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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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$370Average$446FlexibilityNo cancel feeOn-time62%
DeltaCheapest$395Average$630FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$549Average$724FlexibilityNo cancel feeOn-time63%

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