HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Jamaica

$165+ 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 7/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$448
(Booking.com)

One-way from

$165
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$540

Good round-trip deal

$689 or less

Good one-way deal

$372 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
Search Deals
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 ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Jamaica.
Search Deals
Price to beat on a one-way 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 April 30, 2025.

This Booking.com deal was found by Cheapflights users on 4/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/274:46 pmMDW - MBJ
1 stop15h 04mFrontier
Tue 6/39:08 amMBJ - MDW
1 stop13h 36mFrontier
Deal found 4/29$448
This Delta deal was found by Cheapflights users on 4/29. 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.
Sun 5/116:00 amMDW - MBJ
1 stop9h 30mDelta
Wed 5/141:02 pmMBJ - MDW
1 stop8h 26mDelta
Deal found 4/29$449
This Delta deal was found by Cheapflights users on 4/29. 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.
Fri 6/1312:44 pmMDW - KIN
1 stop7h 16mDelta
Fri 6/209:00 amKIN - MDW
1 stop9h 02mDelta
Deal found 4/29$451
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/59:05 amMDW - MBJ
Nonstop4h 00mSouthwest
Tue 7/82:20 pmMBJ - MDW
Nonstop4h 10mSouthwest
Deal found 4/29$473
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Fri 6/69:12 pmMDW - MBJ
2 stops13h 50mMultiple Airlines
Tue 6/102:02 pmMBJ - MDW
1 stop22h 53mMultiple Airlines
Deal found 4/29$487
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/107:21 pmMDW - MBJ
3 stops23h 05mWestJet
Tue 7/1512:45 pmMBJ - MDW
3 stops28h 54mWestJet
Deal found 4/29$807
This Mytrip deal was found by Cheapflights users on 4/28. 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.
Tue 5/610:20 amMDW - KIN
3 stops23h 40mMultiple Airlines
Tue 5/131:45 pmKIN - MDW
3 stops23h 30mMultiple Airlines
Deal found 4/28$3,176

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 30, 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

Thu 5/29

9:50 am-7:50 am

1 stop22h 00m

Montego Bay Sangster Intl

Sun 6/1

9:38 am-9:32 pm

1 stop11h 54m

$448

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 5/7

6:00 am-11:37 am

1 stop5h 37m

Montego Bay Sangster Intl

Wed 5/14

1:02 pm-9:28 pm

1 stop8h 26m

$449

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 6/13

12:44 pm-8:00 pm

1 stop7h 16m

Kingston Norman Manley

Fri 6/20

9:00 am-6:02 pm

1 stop9h 02m

$451

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/24

9:40 am-1:40 pm

Nonstop4h 00m

Montego Bay Sangster Intl

Thu 5/29

12:00 pm-10:00 pm

1 stop10h 00m

$465

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/24

9:40 am-11:42 am

1 stop26h 02m

Montego Bay Sangster Intl

Thu 5/29

12:07 pm-7:14 pm

2 stops31h 07m

$467

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 7/10

7:21 pm-6:26 pm

3 stops23h 05m

Montego Bay Sangster Intl

Tue 7/15

12:45 pm-5:39 pm

3 stops28h 54m

$807

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 5/6

10:20 am-10:00 am

3 stops23h 40m

Kingston Norman Manley

Tue 5/13

1:45 pm-1:15 pm

3 stops23h 30m

$3,176

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 7/7

9:12 pm-11:02 am

2 stops13h 50m

$165

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 5/28

6:40 am-1:51 pm

1 stop7h 11m

$191

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 6/12

10:26 am-8:00 pm

1 stop9h 34m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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.

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 30, 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 30, 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
4,295 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,826 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $193 on Frontier. Other airlines that offer cheap prices include Delta from $202 and Southwest from $203 one-way.

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

    On average you can expect to pay $582 for a flight from Chicago Midway Airport to Jamaica. The cheapest flight overall is $285 while the most popular route, (Chicago Midway - Montego Bay Sangster Intl) is currently priced at $422.

  • 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
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Montego Bay flights
Midway to Punta Cana flights
O'Hare Intl to Oranjestad flights
Midway to Montego Bay flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
O'Hare Intl to Castries flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Bridgetown flights
Midway to Saint Thomas Island flights
Midway to Oranjestad flights
O'Hare Intl to George Town flights
O'Hare Intl to Providenciales flights
O'Hare Intl to Puerto Plata flights
Midway to Nassau flights
O'Hare Intl to Kingston flights
O'Hare Intl to Santiago de los Caballeros flights
Midway to Providenciales flights
O'Hare Intl to Ponce flights
Midway to Santo Domingo flights
O'Hare Intl to St. John's flights
O'Hare Intl to Road Town flights
Midway to Santiago de los Caballeros flights
Midway to George Town flights
O'Hare Intl to Castries flights
O'Hare Intl to Havana flights
O'Hare Intl to The Valley flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Gustavia flights
Midway to Kingston flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Freeport flights
O'Hare Intl to Basseterre flights
O'Hare Intl to St. George's flights
Midway to Simpson Bay flights
O'Hare Intl to Pointe-à-Pitre flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Port Royal flights
O'Hare Intl to Gregory Town flights
Midway to Castries flights
O'Hare Intl to Georgetown 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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$452Average$821FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$579Average$748FlexibilityNo 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.