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$144+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
1 adult, Economy
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Cheap flight deals from Midway to Jamaica

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Jamaica (JM0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 21, 2025.

Round-trip from

$436
(Kiwi.com)

One-way from

$144
(Kiwi.com)

Good round-trip deal

$822 or less
From Chicago Midway to Jamaica
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One-way flight from Chicago Midway to Jamaica
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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 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
jue. 5/86:30 pmMDW - MBJ
1 stop18h 31mFrontier
lun. 5/122:21 pmMBJ - MDW
1 stop9h 18mFrontier
Deal found 1/21$403
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/246:48 pmMDW - KIN
2 stops16h 33mMultiple Airlines
mié. 2/263:30 pmKIN - MDW
1 stop21h 40mMultiple Airlines
Deal found 1/19$436
This Southwest deal was found by Cheapflights users on 1/21. 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.
dom. 4/69:05 amMDW - MBJ
Nonstop4h 00mSouthwest
mié. 4/912:00 pmMBJ - MDW
1 stop7h 50mSouthwest
Deal found 1/21$476
This Delta deal was found by Cheapflights users on 1/21. 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.
mié. 3/1912:51 pmMDW - MBJ
1 stop7h 53mDelta
mar. 3/257:00 amMBJ - MDW
1 stop9h 14mDelta
Deal found 1/21$481
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
lun. 3/246:38 pmMDW - MBJ
2 stops16h 24mMultiple Airlines
sáb. 3/2912:57 pmMBJ - MDW
1 stop8h 59mMultiple Airlines
Deal found 1/21$527
This Delta deal was found by Cheapflights users on 1/21. 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. 3/1812:51 pmMDW - KIN
1 stop7h 09mDelta
jue. 3/279:00 amKIN - MDW
1 stop7h 14mDelta
Deal found 1/21$711
This WestJet deal was found by Cheapflights users on 1/19. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/201:05 pmMDW - KIN
2 stops25h 25mWestJet
vie. 6/273:30 pmKIN - MDW
2 stops26h 33mWestJet
Deal found 1/19$3,340

Find flights from Midway to Jamaica within your budget

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 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

jue. 5/8

6:30 pm-1:01 pm

1 stop18h 31m

Montego Bay Sangster Intl

lun. 5/12

2:21 pm-11:39 pm

1 stop9h 18m

$403

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

lun. 2/24

6:48 pm-12:21 pm

2 stops16h 33m

Kingston Norman Manley

mié. 2/26

3:30 pm-12:10 pm

1 stop21h 40m

$436

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 4/6

9:05 am-1:05 pm

Nonstop4h 00m

Montego Bay Sangster Intl

mié. 4/9

12:00 pm-7:50 pm

1 stop7h 50m

$476

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mié. 3/19

12:51 pm-8:44 pm

1 stop7h 53m

Montego Bay Sangster Intl

jue. 3/27

7:00 am-4:14 pm

1 stop9h 14m

$481

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 3/24

6:38 pm-11:02 am

2 stops16h 24m

Montego Bay Sangster Intl

sáb. 3/29

12:57 pm-9:56 pm

1 stop8h 59m

$527

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

mar. 3/25

12:51 pm-8:00 pm

1 stop7h 09m

Kingston Norman Manley

mar. 4/1

9:00 am-4:14 pm

1 stop7h 14m

$711

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

vie. 6/20

1:05 pm-2:30 pm

2 stops25h 25m

Kingston Norman Manley

vie. 6/27

3:30 pm-6:03 pm

2 stops26h 33m

$3,340

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar. 2/25

8:47 am-1:43 pm

2 stops27h 56m

$144

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

vie. 5/2

8:30 am-11:18 am

1 stop26h 48m

$151

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar. 3/11

7:30 am-11:30 am

Nonstop4h 00m

$212

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 13 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.

Travel insights for flights from Midway to Jamaica

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

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 $569). 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 21, 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.

Rainfall in Jamaica by month

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

In terms of precipitation, rainfall in Jamaica ranges from 1.6 - 7.1 inches per month. October is typically the wettest month, when rainfall can reach 7.1 in. February is typically the driest time to visit Jamaica when rainfall is around 1.6 in.

Temperature in Jamaica by month

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

If weather is an important factor for your trip to Jamaica, 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 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 21, 2025.
To help decide which airline to fly from Chicago to Jamaica, see what other customers have to say about Delta, Southwest and WestJet. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Comfort

8.1

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Comfort

8.1

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Comfort

8.1

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

WestJet
7.2
Good
2,829 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Comfort

8.1

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,443 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Comfort

8.1

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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

    One-way options have recently been found by users for as low as $154 on Frontier. Other airlines that offer cheap prices include Southwest from $212 and Delta from $222 one-way.

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

    On average you can expect to pay $867 for a flight from Chicago Midway Airport to Jamaica. The cheapest flight overall is $569 while the most popular route, (Chicago Midway - Montego Bay Sangster Intl) is currently priced at $385.

  • 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 $569). 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

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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 Kingston flights
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O'Hare Intl to Aguadilla flights
Midway to Georgetown 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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$458Average$688FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$579Average$724FlexibilityNo cancel feeOn-time63%
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