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Cheap flights from Chicago Midway Airport to Jamaica from $118

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 4/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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.
Southwest Logo
9:55 am - 1:45 pm
MDW
-
MBJ
3h 50mnonstop
Southwest Logo
12:10 pm - 10:35 pm
MBJ
-
MDW
10h 25m
2 stops
$316Southwest
Sat, Apr 11 - Sat, Apr 18
Southwest Logo
6:00 am - 11:55 am
MDW
-
MBJ
5h 55m
1 stop
Southwest Logo
12:55 pm - 7:45 am
MBJ
-
MDW
18h 50m
2 stops
$353Southwest
Tue, Mar 17 - Tue, Mar 24
Delta Logo
6:00 am - 3:17 pm
MDW
-
MBJ
9h 17m
1 stop
Delta Logo
2:10 pm - 10:28 pm
MBJ
-
MDW
8h 18m
1 stop
$372Delta
Wed, Apr 29 - Sat, May 2
Delta Logo
6:36 pm - 1:16 pm
MDW
-
MBJ
18h 40m
2 stops
Delta Logo
12:55 pm - 9:09 pm
MBJ
-
MDW
8h 14m
1 stop
$377Delta
Mon, May 18 - Sat, May 23
Delta Logo
6:00 am - 3:19 pm
MDW
-
MBJ
8h 19m
1 stop
Delta Logo
11:15 am - 10:31 pm
MBJ
-
MDW
11h 16m
1 stop
$382Delta
Sun, Mar 1 - Wed, Mar 11
Southwest Logo
11:10 am - 2:55 pm
MDW
-
MBJ
3h 45mnonstop
Southwest Logo
12:55 pm - 10:40 pm
MBJ
-
MDW
9h 45m
1 stop
$384Southwest
Sun, Mar 8 - Wed, Mar 11
Delta Logo
6:00 am - 3:17 pm
MDW
-
MBJ
9h 17m
1 stop
Delta Logo
2:10 pm - 10:28 pm
MBJ
-
MDW
8h 18m
1 stop
$388Delta
Fri, May 1 - Tue, May 5
Frontier Logo
6:00 am - 9:17 am
MDW
-
MBJ
26h 17m
1 stop
Frontier Logo
12:40 pm - 9:39 pm
MBJ
-
MDW
9h 59m
1 stop
$392Frontier
Sat, Feb 21 - Sat, Feb 28
Delta Logo
6:00 am - 3:19 pm
MDW
-
MBJ
8h 19m
1 stop
Delta Logo
11:15 am - 10:31 pm
MBJ
-
MDW
11h 16m
1 stop
$402Delta
Sun, Mar 1 - Wed, Mar 11
Frontier Logo
6:00 am - 2:23 pm
MDW
-
MBJ
8h 23m
1 stop
Frontier Logo
1:57 pm - 8:07 pm
MBJ
-
MDW
30h 10m
1 stop
$405Frontier
Thu, Apr 2 - Mon, Apr 6

Southwest flights from Chicago Midway Airport to Jamaica

Our best Southwest deals on Chicago Midway Airport to Jamaica flight tickets
Southwest
Apr 11
MDW9:55 amChicago Midway
3h 50m
MBJ1:45 pmMontego Bay Sangster Intl
Apr 18
MBJ12:10 pmMontego Bay Sangster Intl
10h 25m
2 stops
MDW10:35 pmChicago Midway
$316
Southwest
Apr 24
MDW7:10 amChicago Midway
6h 45m
1 stop
MBJ1:55 pmMontego Bay Sangster Intl
Apr 27
MBJ2:25 pmMontego Bay Sangster Intl
9h 15m
1 stop
MDW11:40 pmChicago Midway
$336
Southwest
Mar 17
MDW6:00 amChicago Midway
5h 55m
1 stop
MBJ11:55 amMontego Bay Sangster Intl
Mar 24
MBJ12:55 pmMontego Bay Sangster Intl
18h 50m
2 stops
MDW7:45 amChicago Midway
$353

Frontier flights from Chicago Midway Airport to Jamaica

Our best Frontier deals on Chicago Midway Airport to Jamaica flight tickets
Frontier
Apr 2
MDW6:00 amChicago Midway
8h 23m
1 stop
MBJ2:23 pmMontego Bay Sangster Intl
Apr 6
MBJ1:57 pmMontego Bay Sangster Intl
30h 10m
1 stop
MDW8:07 pmChicago Midway
$405
Frontier
Apr 2
MDW6:00 amChicago Midway
8h 23m
1 stop
MBJ2:23 pmMontego Bay Sangster Intl
Apr 6
MBJ1:57 pmMontego Bay Sangster Intl
8h 22m
1 stop
MDW10:19 pmChicago Midway
$406
Frontier
Apr 2
MDW6:00 amChicago Midway
8h 23m
1 stop
MBJ2:23 pmMontego Bay Sangster Intl
Apr 11
MBJ9:01 amMontego Bay Sangster Intl
11h 06m
1 stop
MDW8:07 pmChicago Midway
$426

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 February 19, 2026.
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

Sat 4/11

9:55 am-1:45 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Sat 4/18

12:10 pm-10:35 pm

2 stops10h 25m

$316

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 3/17

6:00 am-11:55 am

1 stop5h 55m

Montego Bay Sangster Intl

Tue 3/24

12:55 pm-7:45 am

2 stops18h 50m

$353

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 4/29

6:00 am-3:17 pm

1 stop9h 17m

Montego Bay Sangster Intl

Sat 5/2

2:10 pm-10:28 pm

1 stop8h 18m

$372

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 5/18

6:36 pm-1:16 pm

2 stops18h 40m

Montego Bay Sangster Intl

Sat 5/23

12:55 pm-9:09 pm

1 stop8h 14m

$377

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 3/1

6:00 am-3:19 pm

1 stop8h 19m

Montego Bay Sangster Intl

Wed 3/11

11:15 am-10:31 pm

1 stop11h 16m

$382

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 3/8

11:10 am-2:55 pm

Nonstop3h 45m

Montego Bay Sangster Intl

Wed 3/11

12:55 pm-10:40 pm

1 stop9h 45m

$384

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 5/1

6:00 am-3:17 pm

1 stop9h 17m

Montego Bay Sangster Intl

Tue 5/5

2:10 pm-10:28 pm

1 stop8h 18m

$388

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 2/21

6:00 am-9:17 am

1 stop26h 17m

Montego Bay Sangster Intl

Sat 2/28

12:40 pm-9:39 pm

1 stop9h 59m

$392

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 3/1

6:00 am-3:19 pm

1 stop8h 19m

Montego Bay Sangster Intl

Wed 3/11

11:15 am-10:31 pm

1 stop11h 16m

$402

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 4/2

6:00 am-2:23 pm

1 stop8h 23m

Montego Bay Sangster Intl

Mon 4/6

1:57 pm-8:07 pm

1 stop30h 10m

$405

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 September. Flight prices, which tend to average around $568, 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 September, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $582.

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 Sunday when prices can be found for as low as $523. This is often the case because there is less demand to fly during this day of the week. On the other hand, Thursday 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 $862.

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?

You could potentially save up to 15% on your flight if you consider stops on a Chicago Midway Airport to Jamaica flight.

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 45m

Direct flights

Mon, Tue, Fri, Sat and Sun

Airports in Jamaica

11 airports
The fastest flight from Chicago Midway Airport to Jamaica takes 3h 45m
Direct flights go from Chicago Midway Airport to Jamaica on Monday, Tuesday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There are 11 airports in Jamaica. From Chicago Midway Airport there are direct flights to 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 $341Free CancellationRating
5.7
3,048 reviews
Search Frontier flights
DeltaPriceFrom $395Free CancellationRating
7.9
8,212 reviews
Search Delta flights
SouthwestPriceFrom $518Free CancellationRating
8.0
4,295 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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