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$172+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MDW
févr. 25 — mars 41
mar. 2/25
mar. 3/4
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 février 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$414
(Delta)

One-way from

$172
(Kiwi.com)

Popular in

January

Cheapest in

April

Average price

$480

Good round-trip deal

$568 or less

Good one-way deal

$396 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. 12% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in February 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 février 20, 2025.

This Delta deal was found by Cheapflights users on 2/19. 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.
mer. 3/197:00 amMBJ - MDW
2 stops11h 02mDelta
mer. 3/266:00 amMDW - MBJ
1 stop9h 23mDelta
Deal found 2/19$414
This Southwest deal was found by Cheapflights users on 2/19. 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.
mer. 3/193:00 pmMBJ - MDW
1 stop8h 00mSouthwest
mer. 3/266:30 amMDW - MBJ
1 stop7h 30mSouthwest
Deal found 2/19$544

Find flights from Jamaica to Midway within your budget

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 février 20, 2025.

Fly from

Jamaica

Fly to

Midway

Route

Depart

Return

Price

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

mer. 3/19

7:00 am-6:02 pm

2 stops11h 02m

Chicago Midway

mer. 3/26

6:00 am-3:23 pm

1 stop9h 23m

$414

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

mer. 3/19

3:00 pm-11:00 pm

1 stop8h 00m

Chicago Midway

mer. 3/26

6:30 am-2:00 pm

1 stop7h 30m

$544

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

jeu. 5/8

2:21 pm-11:39 pm

1 stop9h 18m

$172

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

mar. 3/18

12:07 pm-4:55 pm

2 stops28h 48m

$178

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

mer. 3/19

7:00 am-6:02 pm

2 stops11h 02m

$248

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

jeu. 4/3

2:50 pm-1:10 am

1 stop10h 20m

$273

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

mar. 3/25

7:25 pm-6:18 pm

3 stops22h 53m

$406

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

Travel insights for flights from Jamaica to Midway

Get recent, data-driven insights about flights from Jamaica to Midway including ideal travel times, pricing trends, and more.

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 février 20, 2025.

It’s typically best to fly out from Jamaica to Chicago Midway Airport in the morning. Doing so could potentially save you 22% 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 février 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

WestJet
7.2
Good
2,801 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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?

    $172 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Delta and Southwest, with prices starting from $248 and $273, 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 $547, our data shows the cheapest flight currently is $335. When looking at the most popular route, (Montego Bay Sangster Intl - Chicago Midway), you can expect to pay $355 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top airline flying from Jamaica to Midway

Discover the top airline 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 février 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$332Average$332FlexibilityNo cancel feeOn-timeN/A
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