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$177+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MDW
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap 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 December 15, 2025.

This Frontier deal was found by Cheapflights users on 12/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/273:34 pmMBJ - MDW
1 stop7h 38mFrontier
Sat 1/36:12 amMDW - MBJ
1 stop7h 17mFrontier
Deal found 12/13$351
This Southwest deal was found by Cheapflights users on 12/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/271:55 pmMBJ - MDW
Nonstop4h 10mSouthwest
Sat 1/310:25 amMDW - MBJ
Nonstop3h 55mSouthwest
Deal found 12/13$493
This Delta deal was found by Cheapflights users on 12/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/278:00 amMBJ - MDW
2 stops10h 26mDelta
Sat 1/39:29 amMDW - MBJ
2 stops10h 12mDelta
Deal found 12/13$744

Find flight deals from Jamaica to Midway

Keep the following information in mind while searching for Jamaica to Midway flight deals. Data was last updated December 15, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$346
(Delta)

One-way from

$177
(Trip.com)

Popular in

February

Cheapest in

November

Average price

$441
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.
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From Jamaica to Chicago Midway
Search Deals
One-way flight from Jamaica to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 15, 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

Tue 1/27

12:38 pm-10:22 pm

1 stop10h 44m

Chicago Midway

Tue 2/3

6:00 am-12:54 pm

1 stop5h 54m

$346

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 3/1

4:44 pm-10:42 pm

1 stop6h 58m

Chicago Midway

Wed 3/4

6:00 am-3:19 pm

1 stop8h 19m

$416

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 12/27

1:55 pm-5:05 pm

Nonstop4h 10m

Chicago Midway

Sat 1/3

10:25 am-3:20 pm

Nonstop3h 55m

$493

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 3/1

1:30 pm-12:55 am

2 stops12h 25m

Chicago Midway

Wed 3/4

6:50 am-2:10 pm

1 stop6h 20m

$632

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 12/27

8:00 am-5:26 pm

2 stops10h 26m

Chicago Midway

Sat 1/3

9:29 am-8:41 pm

2 stops10h 12m

$744

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 3/1

1:25 pm-5:37 pm

2 stops29h 12m

Chicago Midway

Wed 3/4

9:50 am-1:49 pm

2 stops26h 59m

$1,318

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 2/28

10:05 am-9:18 pm

1 stop12h 13m

$196

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 1/22

2:19 pm-10:22 pm

1 stop9h 03m

$219

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 1/16

12:38 pm-10:07 pm

1 stop10h 29m

$219

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 1/23

12:38 pm-10:22 pm

1 stop10h 44m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 16 results
1
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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 December 15, 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
7.9
Good
4,250 reviews

Entertainment

7.5

Comfort

8.0

Overall

7.9

Boarding

8.1

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Comfort

8.0

Overall

7.9

Boarding

8.1

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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. Delta provides one of the quickest options available for as low as $493. Airlines will cover a distance of 1709 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$392Average$536FlexibilityNo cancel feeOn-time63%

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