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Jamaica

$124+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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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 November 6, 2025.

This Southwest deal was found by Cheapflights users on 11/5. 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 12/165:05 amMDW - MBJ
1 stop6h 45mSouthwest
Tue 12/233:55 pmMBJ - MDW
1 stop8h 10mSouthwest
Deal found 11/5$371
This Delta deal was found by Cheapflights users on 11/4. 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 12/249:29 amMDW - MBJ
2 stops24h 36mDelta
Sun 12/284:15 pmMBJ - MDW
2 stops17h 34mDelta
Deal found 11/4$376
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/15:47 pmMDW - MBJ
2 stops17h 15mMultiple Airlines
Thu 12/113:26 pmMBJ - MDW
1 stop7h 46mMultiple Airlines
Deal found 11/4$395
This Delta deal was found by Cheapflights users on 11/4. 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.
Sat 12/136:00 amMDW - MBJ
1 stop9h 33mDelta
Tue 12/308:00 amMBJ - MDW
1 stop9h 20mDelta
Deal found 11/4$408
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/128:42 pmMDW - MBJ
1 stop18h 09mMultiple Airlines
Tue 12/161:05 pmMBJ - MDW
2 stops20h 41mMultiple Airlines
Deal found 11/5$416
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/171:37 pmMDW - MBJ
2 stops21h 25mMultiple Airlines
Thu 11/202:43 pmMBJ - MDW
1 stop24h 57mMultiple Airlines
Deal found 11/4$418
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:14 amMDW - MBJ
1 stop7h 15mFrontier
Thu 12/253:47 pmMBJ - MDW
1 stop7h 25mFrontier
Deal found 11/4$422
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/286:05 amMDW - MBJ
1 stop8h 10mMultiple Airlines
Tue 12/21:07 pmMBJ - MDW
2 stops20h 39mMultiple Airlines
Deal found 11/5$423
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:42 pmMDW - MBJ
2 stops14h 28mMultiple Airlines
Mon 1/263:46 pmMBJ - MDW
1 stop8h 39mMultiple Airlines
Deal found 11/4$426
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/156:15 amMDW - MBJ
1 stop8h 00mFrontier
Thu 11/202:43 pmMBJ - MDW
1 stop24h 57mFrontier
Deal found 11/5$431
This Delta deal was found by Cheapflights users on 11/4. 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 12/249:29 amMDW - MBJ
2 stops24h 36mDelta
Fri 12/263:38 pmMBJ - MDW
1 stop7h 44mDelta
Deal found 11/4$436
This CheapOair deal was found by Cheapflights users on 11/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:23 pmMDW - MBJ
1 stop19h 15mFrontier
Mon 12/83:31 pmMBJ - MDW
1 stop7h 41mFrontier
Deal found 11/4$441

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 November 6, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$361
(Kiwi.com)

One-way from

$124
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$570
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. 3% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 6, 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

Sun 2/1

6:00 am-3:20 pm

1 stop8h 20m

Montego Bay Sangster Intl

Fri 2/6

4:45 pm-10:26 pm

1 stop6h 41m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 12/16

5:05 am-12:50 pm

1 stop6h 45m

Montego Bay Sangster Intl

Tue 12/23

3:55 pm-11:05 pm

1 stop8h 10m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 2/6

6:00 am-12:54 pm

1 stop5h 54m

Montego Bay Sangster Intl

Wed 2/11

4:45 pm-10:26 pm

1 stop6h 41m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 1/30

6:00 am-12:54 pm

1 stop5h 54m

Montego Bay Sangster Intl

Tue 2/10

12:38 pm-10:26 pm

1 stop10h 48m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 2/10

6:00 am-3:20 pm

1 stop8h 20m

Montego Bay Sangster Intl

Sun 2/15

8:00 am-3:23 pm

1 stop8h 23m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 1/17

11:21 am-8:36 pm

1 stop8h 15m

Montego Bay Sangster Intl

Wed 1/21

12:38 pm-10:26 pm

1 stop10h 48m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/2

6:00 am-3:20 pm

1 stop8h 20m

Montego Bay Sangster Intl

Sat 2/7

4:45 pm-10:26 pm

1 stop6h 41m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 1/24

6:00 am-8:36 pm

1 stop13h 36m

Montego Bay Sangster Intl

Thu 1/29

4:45 pm-10:26 pm

1 stop6h 41m

$371

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 1/31

6:00 am-8:00 pm

1 stop13h 00m

Kingston Norman Manley

Sat 2/7

9:00 am-3:40 pm

1 stop7h 40m

$445

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sun 11/16

6:26 pm-12:01 pm

2 stops16h 35m

Kingston Norman Manley

Sat 11/22

3:30 pm-10:05 am

1 stop19h 35m

$605

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 35 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 November 6, 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 November 6, 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
4,240 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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
7.9
Good
8,001 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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
3,116 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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 8h 20m. Fly via Delta to get the fastest option. Chicago Midway Airport and Jamaica are separated by a distance of 1709 mi.

  • 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 $145 on Frontier. Other airlines that offer cheap prices include Southwest from $162 and Delta from $162 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, 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

Browse thousands of different options on Cheapflights for your next trip

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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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Midway to St. John's flights
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Midway to Kingston flights

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 November 6, 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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