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Jamaica

$160+ 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
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
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 October 16, 2025.

This Delta deal was found by Cheapflights users on 10/15. 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.
Mon 11/36:00 amMDW - MBJ
1 stop7h 20mDelta
Wed 11/123:36 pmMBJ - MDW
2 stops18h 18mDelta
Deal found 10/15$362
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:00 amMDW - MBJ
1 stop7h 20mDelta
Fri 10/312:45 pmMBJ - MDW
1 stop7h 29mDelta
Deal found 10/14$371
This Delta deal was found by Cheapflights users on 10/15. 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 12/26:00 amMDW - MBJ
1 stop6h 04mDelta
Sat 12/65:58 pmMBJ - MDW
1 stop6h 51mDelta
Deal found 10/15$396
This Frontier deal was found by Cheapflights users on 10/14. 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
Sat 12/134:53 pmMBJ - MDW
1 stop7h 12mFrontier
Deal found 10/14$399
This Delta deal was found by Cheapflights users on 10/16. 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.
Mon 10/276:00 amMDW - MBJ
1 stop7h 20mDelta
Fri 10/312:45 pmMBJ - MDW
1 stop7h 29mDelta
Deal found 10/16$409
This Southwest deal was found by Cheapflights users on 10/14. 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.
Tue 12/27:10 amMDW - MBJ
1 stop6h 45mSouthwest
Sat 12/61:10 pmMBJ - MDW
1 stop7h 45mSouthwest
Deal found 10/14$421
This Priceline deal was found by Cheapflights users on 10/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/38:00 amMDW - MBJ
1 stop24h 57mFrontier
Sun 12/711:17 amMBJ - MDW
1 stop7h 47mFrontier
Deal found 10/14$427
This Southwest deal was found by Cheapflights users on 10/16. 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 11/116:40 amMDW - MBJ
1 stop6h 45mSouthwest
Sat 11/151:10 pmMBJ - MDW
1 stop6h 40mSouthwest
Deal found 10/16$428
This Southwest deal was found by Cheapflights users on 10/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/295:25 amMDW - MBJ
1 stop8h 20mSouthwest
Wed 11/51:50 pmMBJ - MDW
1 stop6h 40mSouthwest
Deal found 10/15$429
This Southwest deal was found by Cheapflights users on 10/14. 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.
Mon 11/105:05 amMDW - MBJ
2 stops8h 50mSouthwest
Thu 11/131:50 pmMBJ - MDW
1 stop10h 10mSouthwest
Deal found 10/14$433
This Southwest deal was found by Cheapflights users on 10/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/127:10 amMDW - MBJ
1 stop6h 45mSouthwest
Tue 11/181:50 pmMBJ - MDW
2 stops9h 45mSouthwest
Deal found 10/15$436
This Southwest deal was found by Cheapflights users on 10/14. 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.
Sun 11/307:40 amMDW - MBJ
1 stop6h 15mSouthwest
Wed 12/31:00 pmMBJ - MDW
1 stop9h 05mSouthwest
Deal found 10/14$442

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 October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$362
(Delta)

One-way from

$160
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$583
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 ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 16, 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 2/17

6:00 am-3:15 pm

1 stop8h 15m

Montego Bay Sangster Intl

Wed 2/25

12:35 pm-9:46 pm

1 stop10h 11m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 12/10

5:05 am-12:50 pm

1 stop6h 45m

Montego Bay Sangster Intl

Wed 12/17

1:00 pm-9:05 pm

1 stop9h 05m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 10/28

6:00 am-1:20 pm

1 stop7h 20m

Montego Bay Sangster Intl

Fri 10/31

1:32 pm-10:14 pm

1 stop8h 42m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 2/10

6:00 am-3:15 pm

1 stop8h 15m

Montego Bay Sangster Intl

Thu 2/19

8:00 am-6:34 pm

2 stops11h 34m

$376

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/9

6:00 am-3:15 pm

1 stop8h 15m

Montego Bay Sangster Intl

Thu 2/19

8:00 am-6:34 pm

2 stops11h 34m

$376

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 2/8

5:59 pm-12:47 pm

2 stops17h 48m

Montego Bay Sangster Intl

Wed 2/18

8:00 am-8:50 am

2 stops25h 50m

$376

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 12/2

6:00 am-1:04 pm

1 stop6h 04m

Montego Bay Sangster Intl

Sat 12/6

5:58 pm-11:49 pm

1 stop6h 51m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 1/9

6:00 am-8:25 pm

1 stop13h 25m

Montego Bay Sangster Intl

Sun 1/18

8:00 am-9:46 pm

1 stop14h 46m

$421

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 1/10

6:00 am-8:25 pm

1 stop13h 25m

Montego Bay Sangster Intl

Sat 1/17

12:45 pm-6:34 pm

1 stop6h 49m

$421

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 1/7

6:00 am-8:00 pm

1 stop13h 00m

Kingston Norman Manley

Sat 1/10

4:59 pm-6:34 pm

2 stops26h 35m

$506

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/16

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 October 16, 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 October 16, 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
4,241 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

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
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

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
3,137 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

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 6h 45m. Fly via Delta or Southwest 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.

  • 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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$370Average$436FlexibilityNo cancel feeOn-time62%
DeltaCheapest$395Average$630FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$549Average$723FlexibilityNo cancel feeOn-time63%

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