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Jamaica

$155+ 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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Aug 12 — Aug 191
Tue 8/12
Tue 8/19
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 August 7, 2025.

Round-trip from

$384
(Frontier)

One-way from

$153
(Trip.com)

Popular in

March

Cheapest in

February

Average price

$568

Good round-trip deal

$536 or less
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 ($16 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 August 2025
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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 August 7, 2025.

This Frontier deal was found by Cheapflights users on 8/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:20 amMDW - MBJ
1 stop6h 25mFrontier
Sun 10/52:12 pmMBJ - MDW
1 stop9h 08mFrontier
Deal found 8/5$384
This FlightHub deal was found by Cheapflights users on 8/5. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/158:00 amMDW - MBJ
1 stop23h 53mFrontier
Sat 10/189:13 amMBJ - MDW
1 stop13h 56mFrontier
Deal found 8/5$385
This FlightHub deal was found by Cheapflights users on 8/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/267:23 pmMDW - MBJ
1 stop12h 30mFrontier
Sun 11/210:13 amMBJ - MDW
1 stop14h 12mFrontier
Deal found 8/6$387
This Delta deal was found by Cheapflights users on 8/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/139:35 amMDW - MBJ
2 stops25h 48mDelta
Wed 10/222:45 pmMBJ - MDW
1 stop7h 29mDelta
Deal found 8/6$389
This Frontier deal was found by Cheapflights users on 8/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/186:20 amMDW - MBJ
1 stop8h 20mFrontier
Sun 9/282:12 pmMBJ - MDW
1 stop9h 08mFrontier
Deal found 8/5$390
This FlightHub deal was found by Cheapflights users on 8/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/316:15 amMDW - MBJ
1 stop25h 40mFrontier
Sat 9/62:05 pmMBJ - MDW
2 stops22h 39mFrontier
Deal found 8/6$391
This FlightHub deal was found by Cheapflights users on 8/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/237:23 pmMDW - MBJ
1 stop12h 30mFrontier
Sun 10/269:13 amMBJ - MDW
1 stop14h 12mFrontier
Deal found 8/6$393
This Frontier deal was found by Cheapflights users on 8/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/186:20 amMDW - MBJ
1 stop8h 20mFrontier
Thu 9/252:12 pmMBJ - MDW
1 stop9h 08mFrontier
Deal found 8/5$394
This Expedia deal was found by Cheapflights users on 8/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2111:03 amMDW - MBJ
1 stop20h 52mFrontier
Thu 9/252:12 pmMBJ - MDW
1 stop25h 48mFrontier
Deal found 8/5$395
This Frontier deal was found by Cheapflights users on 8/6. 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.
Thu 10/97:23 pmMDW - MBJ
1 stop12h 30mFrontier
Mon 10/139:13 amMBJ - MDW
1 stop9h 05mFrontier
Deal found 8/6$396
This FlightHub deal was found by Cheapflights users on 8/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/146:20 amMDW - MBJ
1 stop6h 21mFrontier
Sun 9/282:12 pmMBJ - MDW
1 stop9h 08mFrontier
Deal found 8/6$397
This Frontier deal was found by Cheapflights users on 8/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/196:20 amMDW - MBJ
1 stop6h 25mFrontier
Fri 9/262:12 pmMBJ - MDW
1 stop9h 08mFrontier
Deal found 8/5$399

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 August 7, 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

Thu 10/2

6:20 am-12:45 pm

1 stop6h 25m

Montego Bay Sangster Intl

Sun 10/5

2:12 pm-11:20 pm

1 stop9h 08m

$384

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 10/15

8:00 am-7:53 am

1 stop23h 53m

Montego Bay Sangster Intl

Sat 10/18

9:13 am-11:09 pm

1 stop13h 56m

$385

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 10/26

7:23 pm-7:53 am

1 stop12h 30m

Montego Bay Sangster Intl

Sun 11/2

10:13 am-11:25 pm

1 stop14h 12m

$387

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 10/13

9:35 am-11:23 am

2 stops25h 48m

Montego Bay Sangster Intl

Wed 10/22

2:45 pm-10:14 pm

1 stop7h 29m

$389

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 8/18

6:20 am-2:40 pm

1 stop8h 20m

Montego Bay Sangster Intl

Sun 9/28

2:12 pm-11:20 pm

1 stop9h 08m

$390

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/31

6:15 am-7:55 am

1 stop25h 40m

Montego Bay Sangster Intl

Sat 9/6

2:05 pm-12:44 pm

2 stops22h 39m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 10/23

7:23 pm-7:53 am

1 stop12h 30m

Montego Bay Sangster Intl

Sun 10/26

9:13 am-11:25 pm

1 stop14h 12m

$393

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 8/18

6:20 am-2:40 pm

1 stop8h 20m

Montego Bay Sangster Intl

Thu 9/25

2:12 pm-11:20 pm

1 stop9h 08m

$394

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 8/21

11:03 am-7:55 am

1 stop20h 52m

Montego Bay Sangster Intl

Thu 9/25

2:12 pm-4:00 pm

1 stop25h 48m

$395

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 10/9

7:23 pm-7:53 am

1 stop12h 30m

Montego Bay Sangster Intl

Mon 10/13

9:13 am-6:18 pm

1 stop9h 05m

$396

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/7

Showing 1-10 of 41 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 $561). 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 August 7, 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 August 7, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and WestJet 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
4,247 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,247 reviews
Southwest
8.0
Very good
4,247 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,987 reviews
Southwest
8.0
Very good
4,247 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
WestJet
7.2
Good
3,002 reviews
Southwest
8.0
Very good
4,247 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,230 reviews
Southwest
8.0
Very good
4,247 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • What are the cheapest flights from Chicago Midway Airport to Jamaica?

    On average you can expect to pay $640 for a flight from Chicago Midway Airport to Jamaica. The cheapest flight overall is $518 while the most popular route, (Chicago Midway - Montego Bay Sangster Intl) is currently priced at $364.

  • 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 $561). 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.
O'Hare Intl to Luis Munoz Marin Intl flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
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O'Hare Intl to Saint Thomas Island flights
Midway to Punta Cana flights
O'Hare Intl to Nassau flights
Midway to Montego Bay flights
O'Hare Intl to Providenciales flights
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Midway to Oranjestad flights
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Midway to Saint Thomas Island flights
O'Hare Intl to Bridgetown flights
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Midway to Nassau flights
O'Hare Intl to Christiansted flights
Midway to Providenciales flights
O'Hare Intl to Kingston flights
Midway to Santo Domingo flights
O'Hare Intl to Port of Spain flights
Midway to George Town flights
O'Hare Intl to St. John's flights
Midway to Simpson Bay flights
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Midway to Castries flights
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O'Hare Intl to Gregory Town flights
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Midway to Kingston flights
O'Hare Intl to The Valley flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Fort-de-France flights
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Midway to Santiago de los Caballeros flights

Top 2 airlines flying from Midway to Jamaica

Discover the top 2 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 August 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$458Average$789FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$555Average$724FlexibilityNo cancel feeOn-time63%

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