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$209+ Cheap flights from Jamaica to Midway (MDW)

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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MDW
nov. 15 — nov. 221
sáb. 11/15
sáb. 11/22
1 adult, Economy
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Find flight deals from Jamaica to Midway

Cheapest flights from Jamaica to Midway
Explore the most affordable flight options available from Jamaica to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 16, 2025.

This Southwest deal was found by Cheapflights users on 10/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/201:55 pmMBJ - MDW
Nonstop4h 10mSouthwest
sáb. 1/39:10 amMDW - MBJ
Nonstop3h 55mSouthwest
Deal found 10/15$370
This Southwest deal was found by Cheapflights users on 10/16. 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.
sáb. 11/151:10 pmMBJ - MDW
1 stop6h 40mSouthwest
mié. 11/196:40 amMDW - MBJ
1 stop6h 45mSouthwest
Deal found 10/16$392
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/154:30 pmMBJ - MDW
2 stops18h 56mFrontier
mié. 11/191:56 pmMDW - MBJ
1 stop22h 32mFrontier
Deal found 10/16$427
This Southwest deal was found by Cheapflights users on 10/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/2512:45 pmMBJ - MDW
1 stop8h 15mSouthwest
mié. 11/56:40 amMDW - MBJ
1 stop6h 45mSouthwest
Deal found 10/15$531
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/2512:09 pmMBJ - MDW
2 stops10h 38mMultiple Airlines
mié. 11/52:06 pmMDW - MBJ
1 stop24h 09mMultiple Airlines
Deal found 10/15$634
This Mytrip deal was found by Cheapflights users on 10/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/157:25 pmMBJ - MDW
2 stops15h 40mMultiple Airlines
mié. 11/197:02 pmMDW - MBJ
3 stops23h 21mMultiple Airlines
Deal found 10/16$928
This Mytrip deal was found by Cheapflights users on 10/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/157:25 pmMBJ - MDW
2 stops18h 42mWestJet
mié. 11/197:02 pmMDW - MBJ
3 stops23h 21mWestJet
Deal found 10/16$965

Cheap flight deals from Jamaica to Midway

Keep the following information in mind while searching for Jamaica to Midway flight deals. Data was last updated octubre 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$370
(Southwest)

One-way from

$209
(Delta)

Popular in

January

Cheapest in

September
Provider with most accurate pricing for Montego Bay Sangster Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-Chicago (CHI) flights.
Search Deals
From Jamaica to Chicago Midway
Search Deals
One-way flight from Jamaica to Chicago Midway
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($75 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jamaica to Midway 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 octubre 16, 2025.
Use the filters below to find and compare flights from Jamaica to Chicago Midway Airport that are best for you.

Fly from

Jamaica

Fly to

Midway

Route

Depart

Return

Price

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sáb. 12/20

1:55 pm-5:05 pm

Nonstop4h 10m

Chicago Midway

sáb. 1/3

9:10 am-2:05 pm

Nonstop3h 55m

$370

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sáb. 11/15

1:10 pm-6:50 pm

1 stop6h 40m

Chicago Midway

mié. 11/19

6:40 am-2:25 pm

1 stop6h 45m

$392

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sáb. 11/15

4:30 pm-10:26 am

2 stops18h 56m

Chicago Midway

mié. 11/19

1:56 pm-1:28 pm

1 stop22h 32m

$427

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

vie. 2/6

3:10 pm-9:25 pm

1 stop7h 15m

Chicago Midway

mié. 2/11

6:50 am-2:10 pm

1 stop6h 20m

$468

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

vie. 2/6

8:25 pm-1:08 pm

2 stops17h 43m

Chicago Midway

mié. 2/11

11:00 am-6:05 pm

3 stops30h 05m

$815

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sáb. 11/15

7:25 pm-10:05 am

2 stops15h 40m

Chicago Midway

mié. 11/19

7:02 pm-7:23 pm

3 stops23h 21m

$928

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

jue. 11/13

2:17 pm-11:40 pm

1 stop10h 23m

$209

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

mié. 2/25

8:00 am-4:25 pm

1 stop9h 25m

$209

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

vie. 11/14

3:36 pm-11:40 pm

1 stop9h 04m

$209

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

jue. 2/5

12:35 pm-9:46 pm

1 stop10h 11m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/15

Showing 1-10 of 16 results
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Best time to book a flight from Jamaica to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Jamaica 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 Jamaica to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated octubre 16, 2025.
Peruse reviews from past customers who have flown with Southwest from Jamaica to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Jamaica to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Jamaica to Chicago Midway Airport?

    A quick flight from Jamaica to Chicago Midway Airport can take about 4h 10m. Southwest provides one of the quickest options available for as low as $370. Airlines will cover a distance of 1709 mi. Most flights are nonstop.

  • Can I find deals for flights from Jamaica to Midway that include hotel bookings?

    Yes. In addition to deals on Jamaica to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Jamaica to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Jamaica to Midway.

  • Can I find deals for business class flights from Jamaica to Midway?

    Yes. Cheapflights offers flight deals from Jamaica to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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Alternative routes for Jamaica to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Jamaica to Midway

Discover the top airline that operate flights from Jamaica to Midway. 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 octubre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$392Average$550FlexibilityNo cancel feeOn-time63%

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