HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Jamaica

$136+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
Nov 19 — Nov 261
1 adult
Tue 11/19
Tue 11/26
We work with more than 300 partners to bring you better travel deals

...and more

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

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 November 14, 2024.

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 November 14, 2024.

This Delta deal was found by Cheapflights users on 11/14. 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.
Tue 12/106:00 amMDW - MBJ
1 stop9h 26mDelta
Thu 12/123:29 pmMBJ - MDW
1 stop7h 37mDelta
Deal found 11/14$458
This Kiwi.com deal was found by Cheapflights users on 11/14. 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.
Thu 12/192:31 pmMDW - MBJ
1 stop17h 23mFrontier
Mon 12/2310:14 amMBJ - MDW
1 stop14h 00mFrontier
Deal found 11/14$566
This Kiwi.com deal was found by Cheapflights users on 11/14. 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.
Thu 12/126:15 pmMDW - MBJ
2 stops18h 18mMultiple Airlines
Sun 12/1510:04 amMBJ - MDW
1 stop7h 52mMultiple Airlines
Deal found 11/14$575
This Southwest deal was found by Cheapflights users on 11/14. 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.
Fri 12/68:35 pmMDW - MBJ
2 stops16h 30mSouthwest
Tue 12/101:45 pmMBJ - MDW
2 stops9h 35mSouthwest
Deal found 11/14$624
This Delta deal was found by Cheapflights users on 11/14. 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 12/712:44 pmMDW - KIN
1 stop7h 26mDelta
Tue 12/1010:10 amKIN - MDW
1 stop7h 02mDelta
Deal found 11/14$733
This Mytrip deal was found by Cheapflights users on 11/14. 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.
Fri 12/2011:48 amMDW - MBJ
3 stops25h 05mWestJet
Mon 12/236:50 pmMBJ - MDW
2 stops17h 18mWestJet
Deal found 11/14$2,478
This CheapOair deal was found by Cheapflights users on 11/13. 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.
Sat 12/77:14 pmMDW - KIN
2 stops43h 27mWestJet
Tue 12/104:35 pmKIN - MDW
2 stops21h 56mWestJet
Deal found 11/13$3,455

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 2,752,363 searches. Data last updated November 14, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/17

9:44 pm-7:57 am

1 stop9h 13m

Montego Bay Sangster Intl

Fri 2/28

9:07 am-8:08 pm

2 stops12h 01m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 12/10

6:00 am-4:26 pm

1 stop9h 26m

Montego Bay Sangster Intl

Thu 12/12

3:29 pm-10:06 pm

1 stop7h 37m

$458

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 1/20

5:55 am-3:00 pm

2 stops8h 05m

Montego Bay Sangster Intl

Sat 1/25

2:10 pm-5:25 pm

Nonstop4h 15m

$479

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 1/16

7:21 pm-1:37 pm

2 stops17h 16m

Montego Bay Sangster Intl

Sun 1/19

11:48 am-9:32 pm

1 stop10h 44m

$482

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 12/10

10:38 am-9:10 pm

1 stop9h 32m

Kingston Norman Manley

Tue 12/17

10:10 am-4:12 pm

1 stop7h 02m

$728

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 1/1

11:48 am-1:35 pm

3 stops24h 47m

Kingston Norman Manley

Fri 1/3

4:35 pm-5:44 pm

2 stops26h 09m

$2,186

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 12/7

7:14 pm-3:41 pm

2 stops43h 27m

Kingston Norman Manley

Tue 12/10

4:35 pm-1:31 pm

2 stops21h 56m

$3,455

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 1/11

7:15 am-10:38 am

1 stop26h 23m

$136

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 12/31

7:45 am-1:45 pm

2 stops29h 00m

$148

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 1/1

6:00 am-1:03 pm

1 stop6h 03m

$206

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

Showing 1-10 of 14 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.

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 $401). 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 November 14, 2024.

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 November 14, 2024.
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
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,045 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,788 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,804 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Frontier
6.1
Okay
3,551 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $136 on Frontier. Other airlines that offer cheap prices include Delta from $206 and Southwest from $227 one-way.

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

    On average you can expect to pay $620 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 $353.

  • 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 $401). 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 Nassau flights
O'Hare Intl to Oranjestad flights
Midway to Punta Cana flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to George Town flights
Midway to Montego Bay flights
O'Hare Intl to Providenciales flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to Castries flights
Midway to Oranjestad flights
O'Hare Intl to Willemstad flights
Midway to Nassau flights
O'Hare Intl to Santo Domingo flights
Midway to Saint Thomas Island flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Puerto Plata flights
Midway to Santo Domingo flights
Midway to Providenciales flights
O'Hare Intl to Kingston flights
Midway to Castries flights
O'Hare Intl to Basseterre flights
Midway to George Town flights
Midway to Simpson Bay flights
O'Hare Intl to St. John's flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Freeport flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to St. George's flights
O'Hare Intl to Road Town flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Castries flights
Midway to Kingston flights
O'Hare Intl to Port Au Prince flights
O'Hare Intl to The Valley flights
O'Hare Intl to Havana flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Marsh Harbour flights
Midway to Georgetown flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Pointe-à-Pitre flights
O'Hare Intl to Fort-de-France 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 2,752,363 searches. Data last updated November 14, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$242Average$338FlexibilityNo cancel feeOn-time62%
DeltaCheapest$375Average$683FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$598Average$715FlexibilityNo 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.
View all available airlines