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Cheap flights from Chicago Midway Airport to Jamaica from $147

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Jamaica departing on 1/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to Jamaica

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 2:11 pmMDW-MBJ
7h 11m1 stop
Delta Logo
5:58 pm - 9:54 amMBJ-MDW
16h 56m1 stop
$362Delta
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Mon, Dec 1 - Tue, Dec 9
Frontier Logo
6:00 am - 2:22 pmMDW-MBJ
7h 22m1 stop
Frontier Logo
3:46 pm - 11:25 pmMBJ-MDW
8h 39m1 stop
$363Frontier
Find Deal
Thu, Jan 29 - Sun, Feb 1
Frontier Logo
6:00 am - 2:22 pmMDW-MBJ
7h 22m1 stop
Frontier Logo
3:46 pm - 11:25 pmMBJ-MDW
8h 39m1 stop
$369Frontier
Find Deal
Mon, Feb 2 - Fri, Feb 6
Delta Logo
6:00 am - 12:52 pmMDW-MBJ
5h 52m1 stop
Delta Logo
2:17 pm - 11:40 pmMBJ-MDW
10h 23m1 stop
$371Delta
Find Deal
Thu, Nov 20 - Wed, Nov 26
Frontier Logo
8:42 pm - 3:51 pmMDW-MBJ
18h 09m1 stop
Frontier Logo
4:43 pm - 9:22 pmMBJ-MDW
29h 39m1 stop
$373Frontier
Find Deal
Fri, Dec 5 - Fri, Dec 12
Delta Logo
6:00 am - 4:34 pmMDW-MBJ
9h 34m1 stop
Delta Logo
5:59 pm - 12:34 pmMBJ-MDW
19h 35m2 stops
$376Delta
Find Deal
Thu, Nov 20 - Sun, Nov 23
Multiple Airlines Logo
8:56 pm - 12:05 pmMDW-MBJ
14h 09m2 stops
Multiple Airlines Logo
3:46 pm - 11:25 pmMBJ-MDW
8h 39m1 stop
$384Multiple Airlines
Find Deal
Mon, Feb 2 - Fri, Feb 6
Southwest Logo
7:10 am - 2:55 pmMDW-MBJ
6h 45m1 stop
Southwest Logo
3:55 pm - 11:05 pmMBJ-MDW
8h 10m1 stop
$402Southwest
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Tue, Dec 2 - Fri, Dec 19
Delta Logo
6:00 am - 3:20 pmMDW-MBJ
8h 20m1 stop
Delta Logo
4:45 pm - 10:26 pmMBJ-MDW
6h 41m1 stop
$408Delta
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Tue, Jan 27 - Sat, Jan 31
Southwest Logo
5:05 am - 2:55 pmMDW-MBJ
8h 50m1 stop
Southwest Logo
1:00 pm - 9:15 pmMBJ-MDW
9h 15m2 stops
$479Southwest
Find Deal
Thu, Nov 20 - Wed, Nov 26

Delta flights from Chicago Midway Airport to Jamaica

Our best Delta deals on Chicago Midway Airport to Jamaica flight tickets
Delta
Dec 1
MDW6:00 amChicago Midway
7h 11m
1 stop
MBJ2:11 pmMontego Bay Sangster Intl
Dec 9
MBJ5:58 pmMontego Bay Sangster Intl
16h 56m
1 stop
MDW9:54 amChicago Midway
$362
Find similar
Delta
Nov 20
MDW6:00 amChicago Midway
5h 52m
1 stop
MBJ12:52 pmMontego Bay Sangster Intl
Nov 26
MBJ2:17 pmMontego Bay Sangster Intl
10h 23m
1 stop
MDW11:40 pmChicago Midway
$371
Find similar
Delta
Nov 20
MDW6:00 amChicago Midway
9h 34m
1 stop
MBJ4:34 pmMontego Bay Sangster Intl
Nov 23
MBJ5:59 pmMontego Bay Sangster Intl
19h 35m
2 stops
MDW12:34 pmChicago Midway
$376
Find similar

Southwest flights from Chicago Midway Airport to Jamaica

Our best Southwest deals on Chicago Midway Airport to Jamaica flight tickets
Southwest
Dec 2
MDW7:10 amChicago Midway
6h 45m
1 stop
MBJ2:55 pmMontego Bay Sangster Intl
Dec 19
MBJ3:55 pmMontego Bay Sangster Intl
8h 10m
1 stop
MDW11:05 pmChicago Midway
$402
Find similar
Southwest
Nov 20
MDW5:05 amChicago Midway
8h 50m
1 stop
MBJ2:55 pmMontego Bay Sangster Intl
Nov 26
MBJ1:00 pmMontego Bay Sangster Intl
9h 15m
2 stops
MDW9:15 pmChicago Midway
$479
Find similar
Southwest
Nov 4
MDW5:35 amChicago Midway
8h 20m
2 stops
MBJ2:55 pmMontego Bay Sangster Intl
Nov 6
MBJ3:25 pmMontego Bay Sangster Intl
8h 40m
1 stop
MDW11:05 pmChicago Midway
$484
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated October 30, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 12/1

6:00 am-2:11 pm

1 stop7h 11m

Montego Bay Sangster Intl

Tue 12/9

5:58 pm-9:54 am

1 stop16h 56m

$362

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 1/29

6:00 am-2:22 pm

1 stop7h 22m

Montego Bay Sangster Intl

Sun 2/1

3:46 pm-11:25 pm

1 stop8h 39m

$363

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/2

6:00 am-2:22 pm

1 stop7h 22m

Montego Bay Sangster Intl

Fri 2/6

3:46 pm-11:25 pm

1 stop8h 39m

$369

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 11/20

6:00 am-12:52 pm

1 stop5h 52m

Montego Bay Sangster Intl

Wed 11/26

2:17 pm-11:40 pm

1 stop10h 23m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 12/5

8:42 pm-3:51 pm

1 stop18h 09m

Montego Bay Sangster Intl

Fri 12/12

4:43 pm-9:22 pm

1 stop29h 39m

$373

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 11/20

6:00 am-4:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

Sun 11/23

5:59 pm-12:34 pm

2 stops19h 35m

$376

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/2

8:56 pm-12:05 pm

2 stops14h 09m

Montego Bay Sangster Intl

Fri 2/6

3:46 pm-11:25 pm

1 stop8h 39m

$384

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 12/2

7:10 am-2:55 pm

1 stop6h 45m

Montego Bay Sangster Intl

Fri 12/19

3:55 pm-11:05 pm

1 stop8h 10m

$402

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 1/27

6:00 am-3:20 pm

1 stop8h 20m

Montego Bay Sangster Intl

Sat 1/31

4:45 pm-10:26 pm

1 stop6h 41m

$408

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 11/20

5:05 am-2:55 pm

1 stop8h 50m

Montego Bay Sangster Intl

Wed 11/26

1:00 pm-9:15 pm

2 stops9h 15m

$479

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Jamaica from

How to get the cheapest flight ticket from Chicago Midway Airport to Jamaica

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Jamaica?

The cheapest month to fly to Jamaica from Chicago Midway Airport is in October. Flight prices, which tend to average around $549, are often lower during this time because this is during the off-season. If you aren’t able to travel to Jamaica during the month of October, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $620.

What is the cheapest day to depart on your flight to Jamaica?

The cheapest day to depart on your flight to Jamaica is on a Friday when prices can be found for as low as $579. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $832.

What is the cheapest time of day to depart on your flight to Jamaica?

Our most recent data shows that the best time of day to fly to Jamaica is in the afternoon. Flights from Chicago Midway Airport to Jamaica during this time can be as low as $436. In the morning is when there is more demand to fly to Jamaica, so prices are often more expensive at around $723 per ticket.

What is the cheapest Chicago Midway to Jamaica flight route?

Fly from Chicago Midway to Montego Bay Sangster Intl for the best Chicago Midway - Jamaica flight prices

What cabin class options are available on Chicago Midway to Jamaica flights?

There is only 1 cabin class available to choose from on Chicago Midway to Jamaica flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Jamaica flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Jamaica.

Cheap Chicago Midway Airport to Jamaica flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Jamaica

Fastest flight time

3h 50m

Direct flights

Mon and Sun

Airports in Jamaica

1 airport
The fastest flight from Chicago Midway Airport to Jamaica takes 3h 50m
Direct flights go from Chicago Midway Airport to Jamaica on Monday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Jamaica: Montego Bay Sangster Intl (MBJ)
Search flight deals

  • When did momondo last update prices for flights from Chicago Midway Airport to Jamaica?

    Prices for flights from Chicago Midway Airport to Jamaica were last updated today.

  • How many operators does momondo search for flights from Chicago Midway Airport to Jamaica?

  • How old do you have to be to fly from Chicago Midway Airport to Jamaica?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Jamaica.

  • What documentation or ID do you need to fly to Jamaica?

    The necessary travel and health documents for your Jamaica trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Jamaica?

Best airlines flying from Chicago Midway Airport to Jamaica

Compare and see reviews for airlines that fly from Chicago Midway Airport to Jamaica with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $370Free CancellationRating
5.8
3,123 reviews
Search Frontier flights
DeltaPriceFrom $395Free CancellationRating
7.9
7,993 reviews
Search Delta flights
SouthwestPriceFrom $549Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Jamaica?

It is quick and easy to find Chicago to Jamaica flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Jamaica that suits you.

Can I find flights from Chicago to Jamaica with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Jamaica from Chicago with this policy.

How can momondo help me find flights from Chicago to Jamaica?

momondo helps you find the best flight between Chicago and Jamaica by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Jamaica right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Jamaica flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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