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$177+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$460
(Southwest)

One-way from

$177
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$538

Good round-trip deal

$648 or less

Good one-way deal

$285 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
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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. 0% potential increase in price ($3 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 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 Chicago Midway to Jamaica.
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Price to beat on a one-way 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 April 17, 2025.

This Southwest deal was found by Cheapflights users on 4/16. 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.
Tue 5/66:20 amMDW - MBJ
1 stop7h 35mSouthwest
Sat 5/101:50 pmMBJ - MDW
Nonstop4h 15mSouthwest
Deal found 4/16$460
This CheapOair deal was found by Cheapflights users on 4/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/118:30 amMDW - MBJ
1 stop28h 12mFrontier
Fri 5/162:07 pmMBJ - MDW
1 stop19h 26mFrontier
Deal found 4/16$463
This Delta deal was found by Cheapflights users on 4/16. 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 5/36:04 amMDW - MBJ
1 stop9h 27mDelta
Wed 5/71:02 pmMBJ - MDW
1 stop8h 26mDelta
Deal found 4/16$470
This Delta deal was found by Cheapflights users on 4/16. 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.
Wed 6/1810:26 amMDW - KIN
1 stop9h 34mDelta
Mon 6/239:00 amKIN - MDW
1 stop9h 02mDelta
Deal found 4/16$481
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Sun 5/48:30 amMDW - MBJ
1 stop28h 12mMultiple Airlines
Wed 5/712:07 pmMBJ - MDW
2 stops34h 33mMultiple Airlines
Deal found 4/17$519
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Wed 7/169:40 amMDW - KIN
1 stop11h 05mMultiple Airlines
Sat 7/196:25 pmKIN - MDW
1 stop14h 20mMultiple Airlines
Deal found 4/17$634
This KAYAK deal was found by Cheapflights users on 4/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1712:44 pmMDW - KIN
2 stops25h 46mWestJet
Fri 6/273:30 pmKIN - MDW
2 stops26h 10mWestJet
Deal found 4/15$3,126

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 April 17, 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

Tue 5/6

6:20 am-1:55 pm

1 stop7h 35m

Montego Bay Sangster Intl

Sat 5/10

1:50 pm-6:05 pm

Nonstop4h 15m

$460

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 5/11

8:30 am-12:42 pm

1 stop28h 12m

Montego Bay Sangster Intl

Fri 5/16

2:07 pm-9:33 am

1 stop19h 26m

$463

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/3

6:04 am-3:31 pm

1 stop9h 27m

Montego Bay Sangster Intl

Wed 5/7

1:02 pm-9:28 pm

1 stop8h 26m

$470

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 6/18

10:26 am-8:00 pm

1 stop9h 34m

Kingston Norman Manley

Mon 6/23

9:00 am-6:02 pm

1 stop9h 02m

$481

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 5/4

8:30 am-12:42 pm

1 stop28h 12m

Montego Bay Sangster Intl

Wed 5/7

12:07 pm-10:40 pm

2 stops34h 33m

$519

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 7/16

9:40 am-8:45 pm

1 stop11h 05m

Kingston Norman Manley

Sat 7/19

6:25 pm-8:45 am

1 stop14h 20m

$634

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 6/17

12:44 pm-2:30 pm

2 stops25h 46m

Kingston Norman Manley

Fri 6/27

3:30 pm-5:40 pm

2 stops26h 10m

$3,126

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 5/19

1:19 pm-11:02 am

2 stops21h 43m

$177

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 5/23

8:55 pm-11:53 am

1 stop14h 58m

$195

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 5/18

6:00 am-12:58 pm

1 stop6h 58m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 13 results
1
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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 $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 April 17, 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 April 17, 2025.
To help decide which airline to fly from Chicago to Jamaica, see what other customers have to say about Southwest, Delta 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
8.0
Very good
4,280 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
WestJet
7.2
Good
2,809 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,281 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $195 on Frontier. Other airlines that offer cheap prices include Delta from $201 and Southwest from $217 one-way.

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

    On average you can expect to pay $579 for a flight from Chicago Midway Airport to Jamaica. The cheapest flight overall is $217 while the most popular route, (Chicago Midway - Montego Bay Sangster Intl) is currently priced at $457.

  • 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 Castries flights
O'Hare Intl to Pointe-à-Pitre flights
O'Hare Intl to Port Royal 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$358Average$695FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$579Average$748FlexibilityNo cancel feeOn-time63%

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