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Cheap flights from Chicago Midway Airport to Jamaica from $108

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 5/5. 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.
Frontier Logo
3:07 pm - 12:11 pm
MDW
-
MBJ
21h 04m
2 stops
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
$295Frontier
Tue, May 5 - Tue, May 12
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
$308Frontier
Tue, May 5 - Fri, May 8
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
$318Southwest
Mon, Jul 20 - Thu, Jul 23
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
Frontier Logo
1:16 pm - 11:09 am
MBJ
-
MDW
21h 53m
1 stop
$324Frontier
Fri, May 8 - Mon, May 11
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
Frontier Logo
1:16 pm - 11:09 am
MBJ
-
MDW
21h 53m
1 stop
$325Frontier
Wed, May 13 - Sun, May 17
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
$328Frontier
Tue, May 5 - Thu, May 7
Frontier Logo
11:59 am - 12:11 pm
MDW
-
MBJ
24h 12m
1 stop
Frontier Logo
1:16 pm - 11:09 am
MBJ
-
MDW
21h 53m
1 stop
$332Frontier
Sat, May 9 - Mon, May 11
Delta Logo
6:05 am - 8:00 pm
MDW
-
KIN
13h 55m
1 stop
Delta Logo
9:00 am - 10:17 pm
KIN
-
MDW
13h 17m
1 stop
$556Delta
Tue, Jun 9 - Fri, Jun 12
Delta Logo
9:17 am - 8:00 pm
MDW
-
KIN
10h 43m
2 stops
Delta Logo
9:00 am - 10:17 pm
KIN
-
MDW
13h 17m
1 stop
$561Delta
Tue, Jun 9 - Fri, Jun 12
Delta Logo
10:41 am - 8:00 pm
MDW
-
KIN
9h 19m
1 stop
Delta Logo
9:00 am - 10:28 pm
KIN
-
MDW
13h 28m
1 stop
$576Delta
Thu, Apr 30 - Sun, May 3

Southwest flights from Chicago Midway Airport to Jamaica

Our best Southwest deals on Chicago Midway Airport to Jamaica flight tickets
Southwest
Jul 20
MDW10:05 amChicago Midway
3h 50m
MBJ1:55 pmMontego Bay Sangster Intl
Jul 23
MBJ1:50 pmMontego Bay Sangster Intl
4h 00m
MDW5:50 pmChicago Midway
$318
Southwest
Apr 28
MDW6:00 amChicago Midway
5h 35m
1 stop
MBJ11:35 amMontego Bay Sangster Intl
May 1
MBJ2:55 pmMontego Bay Sangster Intl
7h 25m
1 stop
MDW10:20 pmChicago Midway
$387
Southwest
Jul 8
MDW10:05 amChicago Midway
3h 50m
MBJ1:55 pmMontego Bay Sangster Intl
Jul 15
MBJ1:50 pmMontego Bay Sangster Intl
4h 00m
MDW5:50 pmChicago Midway
$413

Frontier flights from Chicago Midway Airport to Jamaica

Our best Frontier deals on Chicago Midway Airport to Jamaica flight tickets
Frontier
May 5
MDW3:07 pmChicago Midway
21h 04m
2 stops
MBJ12:11 pmMontego Bay Sangster Intl
May 12
MBJ1:16 pmMontego Bay Sangster Intl
8h 46m
1 stop
MDW10:02 pmChicago Midway
$295
Frontier
May 5
MDW6:00 amChicago Midway
6h 11m
1 stop
MBJ12:11 pmMontego Bay Sangster Intl
May 8
MBJ1:16 pmMontego Bay Sangster Intl
8h 46m
1 stop
MDW10:02 pmChicago Midway
$308
Frontier
May 8
MDW6:00 amChicago Midway
6h 11m
1 stop
MBJ12:11 pmMontego Bay Sangster Intl
May 11
MBJ1:16 pmMontego Bay Sangster Intl
21h 53m
1 stop
MDW11:09 amChicago Midway
$324

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 April 9, 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

Cheapest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 5/5

3:07 pm-12:11 pm

2 stops21h 04m

Montego Bay Sangster Intl

Tue 5/12

1:16 pm-10:02 pm

1 stop8h 46m

$295

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 5/5

6:00 am-12:11 pm

1 stop6h 11m

Montego Bay Sangster Intl

Fri 5/8

1:16 pm-10:02 pm

1 stop8h 46m

$308
Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 7/20

10:05 am-1:55 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Thu 7/23

1:50 pm-5:50 pm

Nonstop4h 00m

$318

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 5/8

6:00 am-12:11 pm

1 stop6h 11m

Montego Bay Sangster Intl

Mon 5/11

1:16 pm-11:09 am

1 stop21h 53m

$324

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 5/13

6:00 am-12:11 pm

1 stop6h 11m

Montego Bay Sangster Intl

Sun 5/17

1:16 pm-11:09 am

1 stop21h 53m

$325

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 5/5

6:00 am-12:11 pm

1 stop6h 11m

Montego Bay Sangster Intl

Thu 5/7

1:16 pm-10:02 pm

1 stop8h 46m

$328

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/9

11:59 am-12:11 pm

1 stop24h 12m

Montego Bay Sangster Intl

Mon 5/11

1:16 pm-11:09 am

1 stop21h 53m

$332

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 6/9

6:05 am-8:00 pm

1 stop13h 55m

Kingston Norman Manley

Fri 6/12

9:00 am-10:17 pm

1 stop13h 17m

$556

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 6/9

9:17 am-8:00 pm

2 stops10h 43m

Kingston Norman Manley

Fri 6/12

9:00 am-10:17 pm

1 stop13h 17m

$561

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 4/30

10:41 am-8:00 pm

1 stop9h 19m

Kingston Norman Manley

Sun 5/3

9:00 am-10:28 pm

1 stop13h 28m

$576

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 $525, 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 April is also cheap. Prices for this month can be found on momondo for an average of $550.

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 $518. 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 $992.

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

Best Price Found

$292

Fastest flight time

3h 50m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

Airports in Jamaica

11 airports
The best one-way flight to Jamaica from Chicago Midway Airport in the past 72 hours is $292. The best round-trip flight deal from Chicago Midway Airport to Jamaica found on momondo in the last 72 hours is $307.
The fastest flight from Chicago Midway Airport to Jamaica takes 3h 50m
Direct flights go from Chicago Midway Airport to Jamaica on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is Southwest.
There are 11 airports in Jamaica. From Chicago Midway Airport there are direct flights to Montego Bay Sangster Intl (MBJ).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Jamaica

  • 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
2,995 reviews
Search Frontier flights
DeltaPriceFrom $395Free CancellationRating
7.9
8,392 reviews
Search Delta flights
SouthwestPriceFrom $518Free CancellationRating
8.0
4,338 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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