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$136+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Midway to Jamaica

Keep the following information in mind while searching for Midway to Jamaica flight deals. Data was last updated September 15, 2025.

Round-trip from

$380
(Kiwi.com)

One-way from

$136
(Trip.com)

Popular in

March

Cheapest in

February

Average price

$540
From Chicago Midway to Jamaica
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One-way flight from Chicago Midway to Jamaica
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Highest demand for flights based on searches. 2% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:20 amMDW - MBJ
1 stop8h 55mFrontier
Thu 11/64:30 pmMBJ - MDW
1 stop27h 09mFrontier
Deal found 9/15$380
This Southwest deal was found by Cheapflights users on 9/13. 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.
Sat 10/186:25 amMDW - MBJ
1 stop7h 10mSouthwest
Wed 10/2212:20 pmMBJ - MDW
1 stop8h 30mSouthwest
Deal found 9/13$385
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/38:45 pmMDW - MBJ
2 stops17h 15mSouthwest
Tue 10/71:00 pmMBJ - MDW
1 stop9h 35mSouthwest
Deal found 9/14$389
This Expedia deal was found by Cheapflights users on 9/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/239:26 pmMDW - MBJ
1 stop17h 10mFrontier
Sun 10/263:51 pmMBJ - MDW
1 stop7h 55mFrontier
Deal found 9/13$390
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 11/186:00 amMDW - MBJ
1 stop5h 52mDelta
Wed 11/193:36 pmMBJ - MDW
1 stop8h 56mDelta
Deal found 9/15$391
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:00 amMDW - MBJ
1 stop8h 33mFrontier
Mon 12/154:53 pmMBJ - MDW
1 stop7h 12mFrontier
Deal found 9/14$392
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:15 amMDW - MBJ
1 stop8h 31mFrontier
Fri 10/173:51 pmMBJ - MDW
1 stop7h 55mFrontier
Deal found 9/15$393
This Southwest deal was found by Cheapflights users on 9/13. 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.
Wed 11/195:35 amMDW - MBJ
2 stops8h 20mSouthwest
Tue 11/251:50 pmMBJ - MDW
2 stops10h 15mSouthwest
Deal found 9/13$395
This Frontier deal was found by Cheapflights users on 9/14. 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.
Sat 12/66:00 amMDW - MBJ
1 stop8h 33mFrontier
Sun 12/1411:17 amMBJ - MDW
1 stop12h 48mFrontier
Deal found 9/14$409
This Frontier deal was found by Cheapflights users on 9/15. 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.
Sun 10/126:20 amMDW - MBJ
1 stop8h 16mFrontier
Sun 10/193:51 pmMBJ - MDW
1 stop7h 55mFrontier
Deal found 9/15$413
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1310:12 amMDW - MBJ
2 stops24h 02mMultiple Airlines
Mon 11/174:30 pmMBJ - MDW
1 stop20h 08mMultiple Airlines
Deal found 9/13$415
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/52:06 pmMDW - MBJ
1 stop24h 09mMultiple Airlines
Sat 11/85:39 pmMBJ - MDW
1 stop17h 47mMultiple Airlines
Deal found 9/14$416

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 September 15, 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

Sat 10/18

6:25 am-1:35 pm

1 stop7h 10m

Montego Bay Sangster Intl

Wed 10/22

12:20 pm-8:50 pm

1 stop8h 30m

$385

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 10/18

6:25 am-1:35 pm

1 stop7h 10m

Montego Bay Sangster Intl

Tue 10/21

1:00 pm-12:05 am

2 stops11h 05m

$389

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 10/3

8:45 pm-2:00 pm

2 stops17h 15m

Montego Bay Sangster Intl

Tue 10/7

1:00 pm-10:35 pm

1 stop9h 35m

$389

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 11/17

6:00 am-2:11 pm

1 stop7h 11m

Montego Bay Sangster Intl

Fri 11/21

5:59 pm-11:32 pm

1 stop6h 33m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 11/16

6:00 am-4:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

Wed 11/19

5:59 pm-11:32 pm

1 stop6h 33m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 11/15

6:00 am-4:31 pm

1 stop9h 31m

Montego Bay Sangster Intl

Wed 11/19

3:36 pm-11:32 pm

1 stop8h 56m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 11/19

6:40 am-2:25 pm

1 stop6h 45m

Montego Bay Sangster Intl

Tue 11/25

1:50 pm-9:55 pm

1 stop9h 05m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 11/11

6:00 am-4:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

Fri 11/21

5:59 pm-11:32 pm

1 stop6h 33m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 11/16

6:00 am-2:11 pm

1 stop7h 11m

Montego Bay Sangster Intl

Fri 11/21

5:59 pm-9:51 am

1 stop16h 52m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 10/11

6:15 am-2:46 pm

1 stop8h 31m

Montego Bay Sangster Intl

Fri 10/17

3:51 pm-11:46 pm

1 stop7h 55m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 31 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Jamaica (average of $403). Flying from Chicago Midway Airport to Jamaica in July is currently the most expensive (average of $560). 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 September 15, 2025.

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 Jamaica as you normally would.

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 September 15, 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
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 7h 10m. 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 airlines to fly from Chicago Midway Airport to Jamaica one-way?

    One-way options have recently been found by users for as low as $140 on Frontier. Other airlines that offer cheap prices include Southwest from $152 and Delta from $262 one-way.

  • 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Jamaica (average of $403). Flying from Chicago Midway Airport to Jamaica in July is currently the most expensive (average of $560). 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$370Average$446FlexibilityNo cancel feeOn-time62%
DeltaCheapest$448Average$645FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$549Average$726FlexibilityNo cancel feeOn-time63%

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