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$215+ Cheap flights from Jamaica to Midway (MDW)

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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MDW
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Jamaica to Midway

Keep the following information in mind while searching for Jamaica to Midway flight deals. Data was last updated July 31, 2025.

Round-trip from

$339
(Delta)

One-way from

$215
(Delta)

Popular in

January

Cheapest in

September

Average price

$508

Good round-trip deal

$460 or less

Good one-way deal

$312 or less
From Jamaica to Chicago Midway
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One-way flight from Jamaica to Chicago Midway
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Highest demand for flights based on searches. 9% potential increase in price ($48 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 July 2025
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Price to beat on a round-trip flight from Jamaica to Chicago Midway.
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Price to beat on a one-way flight from Jamaica to Chicago Midway.
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Find flight deals from Jamaica to Midway

Cheapest flights from Jamaica to Midway
Explore the most affordable flight options available from Jamaica to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This Delta deal was found by Cheapflights users on 7/29. 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.
Thu 10/22:35 pmMBJ - MDW
1 stop7h 01mDelta
Mon 10/66:00 amMDW - MBJ
1 stop9h 34mDelta
Deal found 7/29$339
This Southwest deal was found by Cheapflights users on 7/29. 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.
Thu 10/212:50 pmMBJ - MDW
2 stops7h 50mSouthwest
Mon 10/65:00 amMDW - MBJ
1 stop8h 55mSouthwest
Deal found 7/29$348
This Frontier deal was found by Cheapflights users on 7/31. 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 9/142:12 pmMBJ - MDW
1 stop9h 08mFrontier
Sun 9/216:20 amMDW - MBJ
1 stop6h 21mFrontier
Deal found 7/31$352
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 8/79:10 amMBJ - MDW
1 stop14h 07mMultiple Airlines
Mon 8/116:20 amMDW - MBJ
2 stops28h 45mMultiple Airlines
Deal found 7/30$550

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jamaica to Midway 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 July 31, 2025.
Use the filters below to find and compare flights from Jamaica to Chicago Midway Airport that are best for you.

Fly from

Jamaica

Fly to

Midway

Route

Depart

Return

Price

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 10/2

2:35 pm-9:36 pm

1 stop7h 01m

Chicago Midway

Mon 10/6

6:00 am-3:34 pm

1 stop9h 34m

$339

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 10/2

12:50 pm-8:40 pm

2 stops7h 50m

Chicago Midway

Mon 10/6

5:00 am-1:55 pm

1 stop8h 55m

$348

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 9/14

2:12 pm-11:20 pm

1 stop9h 08m

Chicago Midway

Sun 9/21

6:20 am-12:41 pm

1 stop6h 21m

$352

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 9/14

12:45 pm-1:03 pm

2 stops24h 18m

Chicago Midway

Sun 9/21

12:43 pm-9:26 am

2 stops20h 43m

$1,242

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 9/4

1:20 pm-9:26 pm

1 stop8h 06m

$215

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 8/30

9:58 am-11:08 pm

1 stop13h 10m

$216

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 10/9

12:20 pm-10:20 pm

1 stop10h 00m

$220

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 9/6

12:10 pm-9:18 am

2 stops21h 08m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Best time to book a flight from Jamaica to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Jamaica 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 Jamaica to Chicago Midway Airport

What is the cheapest time of day to fly from JM to MDW?

Find hourly flight availability from Jamaica to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

It’s typically best to fly out from Jamaica to Chicago Midway Airport in the morning. Doing so could potentially save you 26% on the flight price compared to flying at noon, which is usually more expensive.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated July 31, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and WestJet from Jamaica to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

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
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

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
2,978 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

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
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

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 Jamaica to Midway. 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 airlines to fly from Jamaica to Chicago Midway Airport one-way?

    $215 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Frontier and Southwest, with prices starting from $216 and $220, respectively.

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

    While on average a flight from Jamaica to Chicago Midway Airport is generally $586, our data shows the cheapest flight currently is $236. When looking at the most popular route, (Montego Bay Sangster Intl - Chicago Midway), you can expect to pay $339 for that flight.

  • Can I find deals for flights from Jamaica to Midway that include hotel bookings?

    Yes. In addition to deals on Jamaica to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Jamaica to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Jamaica to Midway.

  • Can I find deals for business class flights from Jamaica to Midway?

    Yes. Cheapflights offers flight deals from Jamaica to Midway 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 Jamaica to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Jamaica to Chicago Midway Airport (average of $160). Flying from Jamaica to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Alternative routes for Jamaica to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Jamaica to Midway

Discover the top 2 airlines that operate flights from Jamaica to Midway. 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$332Average$332FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$392Average$550FlexibilityNo cancel feeOn-time63%

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