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$159+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$443
(Delta)

One-way from

$159
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$669

Good round-trip deal

$648 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. 4% potential increase in price ($24 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 March 2025
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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 March 28, 2025.

This Delta deal was found by Cheapflights users on 3/27. 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 5/39:52 amMDW - KIN
1 stop10h 08mDelta
Sat 5/109:00 amKIN - MDW
1 stop6h 30mDelta
Deal found 3/27$443
This CheapOair deal was found by Cheapflights users on 3/27. 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.
Thu 5/16:30 pmMDW - MBJ
1 stop18h 38mFrontier
Sun 5/42:28 pmMBJ - MDW
1 stop23h 06mFrontier
Deal found 3/27$463
This Southwest deal was found by Cheapflights users on 3/27. 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 4/285:45 amMDW - MBJ
1 stop8h 50mSouthwest
Wed 5/712:35 pmMBJ - MDW
1 stop9h 30mSouthwest
Deal found 3/27$464
This Delta deal was found by Cheapflights users on 3/27. 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 4/212:51 pmMDW - MBJ
1 stop7h 53mDelta
Wed 4/97:00 amMBJ - MDW
2 stops11h 02mDelta
Deal found 3/27$479
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Sat 4/2611:00 amMDW - MBJ
2 stops23h 55mMultiple Airlines
Sat 5/33:17 pmMBJ - MDW
1 stop22h 17mMultiple Airlines
Deal found 3/27$547
This Mytrip deal was found by Cheapflights users on 3/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/295:20 pmMDW - KIN
1 stop23h 50mMultiple Airlines
Wed 6/46:25 pmKIN - MDW
1 stop14h 20mMultiple Airlines
Deal found 3/27$552

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 March 28, 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

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 5/3

9:52 am-8:00 pm

1 stop10h 08m

Kingston Norman Manley

Sat 5/10

9:00 am-3:30 pm

1 stop6h 30m

$443

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 5/1

6:30 pm-1:08 pm

1 stop18h 38m

Montego Bay Sangster Intl

Sun 5/4

2:28 pm-1:34 pm

1 stop23h 06m

$463

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 4/28

5:45 am-2:35 pm

1 stop8h 50m

Montego Bay Sangster Intl

Wed 5/7

12:35 pm-10:05 pm

1 stop9h 30m

$464

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 4/2

12:51 pm-8:44 pm

1 stop7h 53m

Montego Bay Sangster Intl

Wed 4/9

7:00 am-6:02 pm

2 stops11h 02m

$479

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 4/26

11:00 am-10:55 am

2 stops23h 55m

Montego Bay Sangster Intl

Sat 5/3

3:17 pm-1:34 pm

1 stop22h 17m

$547

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 5/29

5:20 pm-5:10 pm

1 stop23h 50m

Kingston Norman Manley

Wed 6/4

6:25 pm-8:45 am

1 stop14h 20m

$552

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 4/28

1:26 pm-10:55 am

2 stops21h 29m

$159

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 5/27

4:46 pm-7:50 am

1 stop15h 04m

$192

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 4/27

6:04 am-3:31 pm

1 stop9h 27m

$201

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/3

9:40 am-1:40 pm

Nonstop4h 00m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 12 results
1
2

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 March 28, 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 March 28, 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
8.1
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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
7,896 reviews
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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
2,785 reviews
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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
3,271 reviews
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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 $192 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 $859 for a flight from Chicago Midway Airport to Jamaica. The cheapest flight overall is $559 while the most popular route, (Chicago Midway - Montego Bay Sangster Intl) is currently priced at $448.

  • 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.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
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O'Hare Intl to Oranjestad flights
Midway to Montego Bay flights
O'Hare Intl to Nassau flights
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O'Hare Intl to Simpson Bay flights
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Midway to Nassau flights
O'Hare Intl to George Town flights
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Midway to Oranjestad flights
O'Hare Intl to Providenciales flights
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Midway to Providenciales flights
Midway to Simpson Bay flights
O'Hare Intl to St. George's flights
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Midway to Kingston flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Castries flights
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O'Hare Intl to Kralendijk flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Gustavia flights
O'Hare Intl to Havana flights
O'Hare Intl to The Valley flights
Midway to Santiago de los Caballeros flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Culebra flights
Midway to Castries flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Fort-de-France 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$358Average$706FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$579Average$736FlexibilityNo cancel feeOn-time63%
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