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$225+ 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 6/25. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MDW
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$412
(Booking.com)

One-way from

$225
(Kiwi.com)

Popular in

January

Cheapest in

May

Average price

$406

Good round-trip deal

$532 or less

Good one-way deal

$287 or less
Provider with most accurate pricing for Montego Bay Sangster Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-Chicago (CHI) flights.
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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. 8% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 29, 2025.

This Booking.com deal was found by Cheapflights users on 4/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/39:08 amMBJ - MDW
1 stop13h 36mFrontier
Tue 6/105:36 pmMDW - MBJ
1 stop19h 01mFrontier
Deal found 4/29$412
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 5/3111:31 amMBJ - MDW
1 stop9h 42mDelta
Sun 6/86:00 amMDW - MBJ
1 stop9h 25mDelta
Deal found 4/29$462
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/39:08 amMBJ - MDW
1 stop13h 36mMultiple Airlines
Tue 6/105:36 pmMDW - MBJ
2 stops17h 26mMultiple Airlines
Deal found 4/29$476
This Southwest deal was found by Cheapflights users on 4/28. 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 6/92:55 pmMBJ - MDW
2 stops10h 00mSouthwest
Thu 6/129:45 pmMDW - MBJ
2 stops15h 35mSouthwest
Deal found 4/28$717
This WestJet deal was found by Cheapflights users on 4/29. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/37:25 pmMBJ - MDW
2 stops26h 57mWestJet
Thu 7/3112:38 pmMDW - MBJ
2 stops20h 49mWestJet
Deal found 4/29$2,046

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 April 29, 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

Tue 6/3

9:08 am-10:44 pm

1 stop13h 36m

Chicago Midway

Tue 6/10

5:36 pm-12:37 pm

1 stop19h 01m

$412

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 5/31

11:31 am-9:13 pm

1 stop9h 42m

Chicago Midway

Sun 6/8

6:00 am-3:25 pm

1 stop9h 25m

$462

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 6/3

9:08 am-10:44 pm

1 stop13h 36m

Chicago Midway

Tue 6/10

5:36 pm-11:02 am

2 stops17h 26m

$476

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Mon 6/9

2:55 pm-12:55 am

2 stops10h 00m

Chicago Midway

Thu 6/12

9:45 pm-1:20 pm

2 stops15h 35m

$717

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 6/25

12:07 pm-8:17 pm

2 stops32h 10m

$225

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 5/30

9:05 am-10:14 pm

1 stop13h 09m

$246

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 7/9

2:20 pm-6:30 pm

Nonstop4h 10m

$249

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 8/20

1:15 pm-9:47 pm

1 stop8h 32m

$254

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 6/20

12:45 pm-5:12 pm

3 stops28h 27m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 April 29, 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 29, 2025.
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,929 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,823 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,284 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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?

    $246 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $249 and $254, 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 $455, our data shows the cheapest flight currently is $277. When looking at the most popular route, (Montego Bay Sangster Intl - Chicago Midway), you can expect to pay $455 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 Jamaica?

Book flights to Jamaica if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$332Average$332FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$451Average$657FlexibilityNo cancel feeOn-time63%

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