HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Jamaica

$109+ 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
jul. 6 — jul. 131
dom. 7/6
dom. 7/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Jamaica with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 julio 1, 2025.

Round-trip from

$386
(Delta)

One-way from

$109
(Priceline)

Popular in

March

Cheapest in

January

Average price

$613

Good round-trip deal

$549 or less
From Chicago Midway to Jamaica
Search Deals
One-way flight from Chicago Midway to Jamaica
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Jamaica.
Search Deals

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 julio 1, 2025.

This Delta deal was found by Cheapflights users on 6/29. 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.
jue. 8/1410:31 amMDW - KIN
1 stop9h 54mDelta
mié. 8/209:25 amKIN - MDW
1 stop12h 19mDelta
Deal found 6/29$386
This Priceline deal was found by Cheapflights users on 7/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/206:10 amMDW - MBJ
1 stop6h 35mFrontier
sáb. 9/272:05 pmMBJ - MDW
1 stop8h 28mFrontier
Deal found 7/1$401
This Delta deal was found by Cheapflights users on 7/1. 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.
sáb. 9/206:00 amMDW - MBJ
1 stop9h 34mDelta
jue. 9/252:35 pmMBJ - MDW
1 stop7h 01mDelta
Deal found 7/1$410
This Southwest deal was found by Cheapflights users on 6/30. 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. 9/147:55 pmMDW - MBJ
2 stops17h 35mSouthwest
jue. 9/183:00 pmMBJ - MDW
1 stop7h 25mSouthwest
Deal found 6/30$427
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
sáb. 7/269:12 pmMDW - MBJ
2 stops12h 41mMultiple Airlines
sáb. 8/22:09 pmMBJ - MDW
1 stop24h 57mMultiple Airlines
Deal found 7/1$432
This Kiwi.com deal was found by Cheapflights users on 6/29. 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.
jue. 8/147:40 amMDW - KIN
2 stops25h 02mMultiple Airlines
mié. 8/206:25 pmKIN - MDW
1 stop14h 20mMultiple Airlines
Deal found 6/29$451

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 julio 1, 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

jue. 8/14

10:31 am-8:25 pm

1 stop9h 54m

Kingston Norman Manley

mié. 8/20

9:25 am-9:44 pm

1 stop12h 19m

$386

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

sáb. 9/20

6:10 am-12:45 pm

1 stop6h 35m

Montego Bay Sangster Intl

sáb. 9/27

2:05 pm-10:33 pm

1 stop8h 28m

$401

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

sáb. 9/20

6:00 am-3:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

vie. 9/26

2:35 pm-9:36 pm

1 stop7h 01m

$410

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 9/14

7:55 pm-1:30 pm

2 stops17h 35m

Montego Bay Sangster Intl

jue. 9/18

3:00 pm-10:25 pm

1 stop7h 25m

$427

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

sáb. 7/26

9:12 pm-9:53 am

2 stops12h 41m

Montego Bay Sangster Intl

sáb. 8/2

2:09 pm-3:06 pm

1 stop24h 57m

$432

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

jue. 8/14

7:40 am-8:42 am

2 stops25h 02m

Kingston Norman Manley

mié. 8/20

6:25 pm-8:45 am

1 stop14h 20m

$451

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 9/8

6:20 am-12:45 pm

1 stop6h 25m

$109

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 8/3

9:00 am-1:00 pm

Nonstop4h 00m

$164

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 9/29

9:47 pm-11:10 am

2 stops13h 23m

$165

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 9/1

6:00 am-3:36 pm

1 stop9h 36m

$169

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 13 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 julio 1, 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.

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 julio 1, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and WestJet from Chicago Midway Airport to Jamaica to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,273 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
WestJet
7.2
Good
2,909 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,291 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $109 on Frontier. Other airlines that offer cheap prices include Southwest from $164 and Delta from $169 one-way.

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

    On average you can expect to pay $712 for a flight from Chicago Midway Airport to Jamaica. The cheapest flight overall is $455 while the most popular route, (Chicago Midway - Montego Bay Sangster Intl) is currently priced at $383.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
O'Hare Intl to Montego Bay flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Oranjestad flights
Midway to Montego Bay flights
O'Hare Intl to Saint Thomas Island flights
Midway to Punta Cana flights
O'Hare Intl to Nassau flights
O'Hare Intl to Providenciales flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to Castries flights
O'Hare Intl to Willemstad flights
O'Hare Intl to George Town flights
Midway to Oranjestad flights
Midway to Saint Thomas Island flights
Midway to Nassau flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Kingston flights
O'Hare Intl to Port of Spain flights
Midway to Providenciales flights
Midway to Santo Domingo flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to St. John's flights
O'Hare Intl to Road Town flights
Midway to George Town flights
O'Hare Intl to Castries flights
Midway to Santiago de los Caballeros flights
O'Hare Intl to Basseterre flights
O'Hare Intl to St. George's flights
Midway to Simpson Bay flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Freeport flights
O'Hare Intl to Havana flights
O'Hare Intl to Gustavia flights
O'Hare Intl to The Valley flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Aguadilla flights
Midway to Castries flights
O'Hare Intl to Gregory Town flights
Midway to Kingston flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Culebra flights
O'Hare Intl to Mayagüez flights
Midway to Gregory Town flights

Top 3 airlines flying from Midway to Jamaica

Discover the top 3 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 julio 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$338Average$436FlexibilityNo cancel feeOn-time62%
DeltaCheapest$452Average$790FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$555Average$726FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.