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Jamaica

$117+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MBJ
mar 11 — mar 181
mer 3/11
mer 3/18
1 adult, Economy
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Cheap 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 febbraio 9, 2026.

This Delta deal was found by Cheapflights users on 2/7. 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.
dom 3/16:00 am
MDW
-
MBJ
1 stop8h 19m
Delta
gio 4/92:42 pm
MBJ
-
MDW
1 stop18h 08m
Delta
Deal found 2/7$378
This Delta deal was found by Cheapflights users on 2/7. 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.
dom 3/19:34 am
MDW
-
MBJ
2 stops25h 58m
Delta
mar 4/72:42 pm
MBJ
-
MDW
1 stop18h 08m
Delta
Deal found 2/7$383
This Kiwi.com deal was found by Cheapflights users on 2/5. 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.
ven 2/206:48 pm
MDW
-
MBJ
1 stop13h 37m
Multiple Airlines
mar 2/241:00 pm
MBJ
-
MDW
2 stops31h 07m
Multiple Airlines
Deal found 2/5$386
This Delta deal was found by Cheapflights users on 2/8. 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.
gio 4/166:00 am
MDW
-
MBJ
1 stop9h 17m
Delta
mer 4/222:09 pm
MBJ
-
MDW
1 stop8h 19m
Delta
Deal found 2/8$389
This Southwest deal was found by Cheapflights users on 2/5. 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.
sab 2/288:20 am
MDW
-
MBJ
Nonstop3h 55m
Southwest
mer 3/42:00 pm
MBJ
-
MDW
2 stops18h 50m
Southwest
Deal found 2/5$391
This CheapOair deal was found by Cheapflights users on 2/8. 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.
sab 2/216:00 am
MDW
-
MBJ
1 stop26h 17m
Frontier
sab 2/2812:40 pm
MBJ
-
MDW
1 stop9h 59m
Frontier
Deal found 2/8$392
This Delta deal was found by Cheapflights users on 2/6. 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.
mar 2/176:00 am
MDW
-
MBJ
1 stop8h 19m
Delta
gio 2/264:44 pm
MBJ
-
MDW
1 stop6h 47m
Delta
Deal found 2/6$394
This Frontier deal was found by Cheapflights users on 2/7. 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.
dom 2/159:04 pm
MDW
-
MBJ
1 stop10h 56m
Frontier
sab 2/2110:40 am
MBJ
-
MDW
1 stop11h 53m
Frontier
Deal found 2/7$397
This Southwest deal was found by Cheapflights users on 2/8. 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.
mer 3/46:50 am
MDW
-
MBJ
1 stop6h 20m
Southwest
dom 3/812:30 pm
MBJ
-
MDW
Nonstop4h 20m
Southwest
Deal found 2/8$399
This Delta deal was found by Cheapflights users on 2/8. 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.
mer 3/116:00 am
MDW
-
MBJ
1 stop9h 28m
Delta
lun 3/1611:15 am
MBJ
-
MDW
1 stop11h 16m
Delta
Deal found 2/8$408
This Delta deal was found by Cheapflights users on 2/7. 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.
ven 3/66:00 am
MDW
-
KIN
1 stop13h 00m
Delta
mer 3/119:00 am
KIN
-
MDW
1 stop8h 22m
Delta
Deal found 2/7$466
This Delta deal was found by Cheapflights users on 2/5. 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.
mar 3/39:34 am
MDW
-
KIN
2 stops9h 26m
Delta
mar 3/109:00 am
KIN
-
MDW
1 stop8h 22m
Delta
Deal found 2/5$471

Find flight deals from Midway to Jamaica

Keep the following information in mind while searching for Midway to Jamaica flight deals. Data was last updated febbraio 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$378
(Delta)

One-way from

$117
(Trip.com)

Popular in

June

Cheapest in

January

Average price

$546

Good round-trip deal

$509 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. 7% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Jamaica.
Search Deals

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 febbraio 9, 2026.
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

dom 3/1

6:40 pm-11:10 am

1 stop15h 30m

Montego Bay Sangster Intl

mer 4/8

2:42 pm-8:50 am

1 stop18h 08m

$378

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar 3/3

6:00 am-3:19 pm

1 stop8h 19m

Montego Bay Sangster Intl

mer 4/8

2:42 pm-8:50 am

1 stop18h 08m

$378

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun 3/2

6:40 pm-11:10 am

1 stop15h 30m

Montego Bay Sangster Intl

mar 4/7

2:42 pm-8:50 am

1 stop18h 08m

$378

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun 3/2

6:40 pm-11:10 am

1 stop15h 30m

Montego Bay Sangster Intl

gio 4/9

2:42 pm-8:50 am

1 stop18h 08m

$378

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar 3/3

7:20 pm-2:40 pm

1 stop18h 20m

Montego Bay Sangster Intl

mar 4/7

2:42 pm-8:50 am

1 stop18h 08m

$378

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom 3/1

6:40 pm-11:10 am

1 stop15h 30m

Montego Bay Sangster Intl

gio 4/9

2:25 pm-5:54 pm

2 stops27h 29m

$383

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom 3/1

9:34 am-12:32 pm

2 stops25h 58m

Montego Bay Sangster Intl

mar 4/7

2:42 pm-8:50 am

1 stop18h 08m

$383

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mer 4/29

6:00 am-12:54 pm

1 stop6h 54m

Montego Bay Sangster Intl

sab 5/2

2:09 pm-10:28 pm

1 stop8h 19m

$389

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

gio 4/16

6:00 am-11:29 am

1 stop5h 29m

Montego Bay Sangster Intl

mar 4/21

2:09 pm-10:28 pm

1 stop8h 19m

$389

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

sab 4/25

6:00 am-12:54 pm

1 stop6h 54m

Montego Bay Sangster Intl

mer 4/29

12:44 pm-10:28 pm

1 stop9h 44m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/7

Showing 1-10 of 31 results
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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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Jamaica (average of $367). Flying from Chicago Midway Airport to Jamaica in March is currently the most expensive (average of $793). 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.

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 febbraio 9, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and Frontier 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
4,281 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

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
8.0
Very good
4,281 reviews
Southwest
8.0
Very good
4,281 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

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
Delta
7.9
Good
8,174 reviews
Southwest
8.0
Very good
4,281 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

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
Frontier
5.7
Fair
3,051 reviews
Southwest
8.0
Very good
4,281 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

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 Midway to Jamaica. 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 Chicago Midway Airport to Jamaica?

    There are many flights that can get you from Chicago Midway Airport to Jamaica in 15h 30m. Fly via Delta to get the fastest option. Chicago Midway Airport and Jamaica are separated by a distance of 1709 mi.

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

    On average you can expect to pay $735 for a flight from Chicago Midway Airport to Jamaica. The cheapest flight overall is $488 while the most popular route, (Chicago Midway - Montego Bay Sangster Intl) is currently priced at $352.

  • 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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Jamaica (average of $367). Flying from Chicago Midway Airport to Jamaica in March is currently the most expensive (average of $793). 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

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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
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Nassau flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Montego Bay flights
Midway to Punta Cana flights
O'Hare Intl to Providenciales flights
O'Hare Intl to George Town flights
O'Hare Intl to Simpson Bay flights
Midway to Oranjestad flights
O'Hare Intl to Santo Domingo flights
Midway to Nassau flights
Midway to Montego Bay flights
O'Hare Intl to Castries flights
Midway to Saint Thomas Island flights
O'Hare Intl to St. John's flights
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Midway to Providenciales flights
Midway to Simpson Bay flights
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Midway to Castries flights
O'Hare Intl to Basseterre flights
Midway to Kingston flights
O'Hare Intl to Castries flights
O'Hare Intl to Freeport flights
Midway to Georgetown flights
Midway to St. John's flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Gustavia 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 febbraio 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$341Average$446FlexibilityNo cancel feeOn-time62%
DeltaCheapest$395Average$606FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$518Average$719FlexibilityNo cancel feeOn-time63%

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