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Jamaica

$132+ 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 2/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
feb. 7 — feb. 141
sáb. 2/7
sáb. 2/14
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 enero 8, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$396
(Delta)

One-way from

$132
(Trip.com)

Popular in

June

Cheapest in

January

Average price

$532

Good round-trip deal

$459 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
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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. 5% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Chicago Midway to Jamaica.
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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 enero 8, 2026.

This Delta deal was found by Cheapflights users on 1/8. 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.
mar. 2/176:40 pmMDW - MBJ
1 stop15h 30mDelta
vie. 2/2712:20 pmMBJ - MDW
1 stop6h 25mDelta
Deal found 1/8$396
This Priceline deal was found by Cheapflights users on 1/7. 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.
jue. 2/126:25 amMDW - MBJ
1 stop6h 28mFrontier
lun. 2/1610:05 amMBJ - MDW
1 stop10h 42mFrontier
Deal found 1/7$399
This Priceline deal was found by Cheapflights users on 1/7. 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.
sáb. 3/146:00 amMDW - MBJ
1 stop8h 17mFrontier
sáb. 3/213:32 pmMBJ - MDW
2 stops21h 30mFrontier
Deal found 1/7$409
This Delta deal was found by Cheapflights users on 1/8. 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.
lun. 1/266:00 amMDW - MBJ
1 stop5h 54mDelta
vie. 2/64:45 pmMBJ - MDW
1 stop6h 37mDelta
Deal found 1/8$416
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
vie. 1/235:01 pmMDW - MBJ
1 stop19h 29mMultiple Airlines
lun. 1/2612:57 pmMBJ - MDW
2 stops10h 22mMultiple Airlines
Deal found 1/6$417
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
vie. 1/305:01 pmMDW - MBJ
1 stop19h 29mMultiple Airlines
vie. 2/612:57 pmMBJ - MDW
2 stops10h 22mMultiple Airlines
Deal found 1/6$420
This Delta deal was found by Cheapflights users on 1/8. 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.
vie. 2/206:00 amMDW - MBJ
1 stop8h 19mDelta
jue. 2/264:44 pmMBJ - MDW
1 stop6h 47mDelta
Deal found 1/8$421
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
vie. 2/61:00 pmMDW - MBJ
2 stops22h 02mMultiple Airlines
vie. 2/1310:05 amMBJ - MDW
1 stop8h 48mMultiple Airlines
Deal found 1/7$425
This Frontier deal was found by Cheapflights users on 1/6. 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.
dom. 2/159:04 pmMDW - MBJ
1 stop10h 56mFrontier
sáb. 2/2110:40 amMBJ - MDW
1 stop11h 53mFrontier
Deal found 1/6$426
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
vie. 2/136:48 pmMDW - MBJ
1 stop14h 51mMultiple Airlines
lun. 2/161:00 pmMBJ - MDW
2 stops31h 07mMultiple Airlines
Deal found 1/6$428
This Frontier deal was found by Cheapflights users on 1/7. 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.
vie. 4/36:00 amMDW - MBJ
1 stop8h 46mFrontier
sáb. 4/114:06 pmMBJ - MDW
1 stop7h 36mFrontier
Deal found 1/7$429
This Delta deal was found by Cheapflights users on 1/7. 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.
sáb. 2/216:00 amMDW - KIN
1 stop13h 00mDelta
sáb. 2/289:00 amKIN - MDW
1 stop14h 31mDelta
Deal found 1/7$446

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 enero 8, 2026.
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

lun. 3/2

6:00 am-12:53 pm

1 stop5h 53m

Montego Bay Sangster Intl

mié. 3/4

12:20 pm-5:45 pm

1 stop6h 25m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mié. 2/25

6:00 am-12:53 pm

1 stop5h 53m

Montego Bay Sangster Intl

mié. 3/4

4:44 pm-10:31 pm

1 stop6h 47m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 2/23

6:40 pm-11:10 am

1 stop15h 30m

Montego Bay Sangster Intl

mar. 3/3

4:44 pm-10:33 pm

1 stop6h 49m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 2/23

6:00 am-3:19 pm

1 stop8h 19m

Montego Bay Sangster Intl

mié. 2/25

4:44 pm-10:31 pm

1 stop6h 47m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mié. 2/18

6:00 am-3:19 pm

1 stop8h 19m

Montego Bay Sangster Intl

mar. 3/3

2:19 pm-10:33 pm

1 stop9h 14m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar. 2/17

6:40 pm-11:10 am

1 stop15h 30m

Montego Bay Sangster Intl

vie. 2/27

12:20 pm-5:45 pm

1 stop6h 25m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 3/1

6:00 am-12:53 pm

1 stop5h 53m

Montego Bay Sangster Intl

jue. 3/5

12:20 pm-5:45 pm

1 stop6h 25m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mié. 2/18

7:20 pm-2:40 pm

1 stop18h 20m

Montego Bay Sangster Intl

mié. 2/25

4:44 pm-10:31 pm

1 stop6h 47m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 2/22

7:20 pm-2:40 pm

1 stop18h 20m

Montego Bay Sangster Intl

mar. 3/3

2:19 pm-10:33 pm

1 stop9h 14m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 1/26

6:00 am-12:54 pm

1 stop5h 54m

Montego Bay Sangster Intl

vie. 2/6

4:45 pm-10:22 pm

1 stop6h 37m

$416

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 36 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 $595). 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 enero 8, 2026.

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 enero 8, 2026.
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
4,250 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

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
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

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
8,026 reviews
Southwest
8.0
Very good
4,250 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

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
5.7
Fair
3,061 reviews
Southwest
8.0
Very good
4,250 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

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 5h 53m. 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 flights from Chicago Midway Airport to Jamaica?

    On average you can expect to pay $486 for a flight from Chicago Midway Airport to Jamaica. The cheapest flight overall is $420 while the most popular route, (Chicago Midway - Montego Bay Sangster Intl) is currently priced at $359.

  • 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 $595). 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 Castries flights
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O'Hare Intl to Kingstown 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 enero 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$341Average$446FlexibilityNo cancel feeOn-time62%
DeltaCheapest$395Average$630FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$549Average$724FlexibilityNo cancel feeOn-time63%

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