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Cheap flights from Chicago Midway Airport to Jamaica from $197

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 10/27. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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 - 4:35 pm
MDW
-
MBJ
9h 35m
1 stop
Delta Logo
2:20 pm - 10:56 pm
MBJ
-
MDW
9h 36m
1 stop
$442Delta
Fri, Dec 4 - Wed, Dec 9
Delta Logo
6:00 am - 4:35 pm
MDW
-
MBJ
9h 35m
1 stop
Delta Logo
3:40 pm - 10:56 pm
MBJ
-
MDW
8h 16m
1 stop
$442Delta
Mon, Nov 9 - Fri, Nov 13
Southwest Logo
5:55 am - 12:25 pm
MDW
-
MBJ
6h 30m
1 stop
Southwest Logo
1:55 pm - 8:45 pm
MBJ
-
MDW
6h 50m
1 stop
$442Southwest
Sat, Aug 29 - Wed, Sep 2
Southwest Logo
7:10 am - 2:25 pm
MDW
-
MBJ
7h 15m
1 stop
Southwest Logo
12:55 pm - 9:00 pm
MBJ
-
MDW
8h 05m
1 stop
$442Southwest
Sun, Sep 13 - Wed, Sep 16
Delta Logo
6:00 am - 4:35 pm
MDW
-
MBJ
9h 35m
1 stop
Delta Logo
2:20 pm - 10:56 pm
MBJ
-
MDW
9h 36m
1 stop
$442Delta
Sat, Dec 5 - Thu, Dec 10
Southwest Logo
5:45 am - 11:50 am
MDW
-
MBJ
6h 05m
1 stop
Southwest Logo
1:00 pm - 11:05 pm
MBJ
-
MDW
11h 05m
1 stop
$442Southwest
Wed, Oct 28 - Mon, Nov 2
Frontier Logo
6:25 am - 2:27 pm
MDW
-
MBJ
8h 02m
1 stop
Frontier Logo
3:42 pm - 11:44 pm
MBJ
-
MDW
8h 02m
1 stop
$481Frontier
Mon, Sep 14 - Mon, Sep 21
Frontier Logo
6:25 am - 2:27 pm
MDW
-
MBJ
8h 02m
1 stop
Frontier Logo
3:42 pm - 11:44 pm
MBJ
-
MDW
8h 02m
1 stop
$482Frontier
Sun, Sep 13 - Sun, Sep 20
Air France Logo
9:29 am - 8:10 pm
MDW
-
KIN
10h 41m
2 stops
Air France Logo
9:10 am - 6:33 pm
KIN
-
MDW
9h 23m
2 stops
$547Air France
Thu, Sep 24 - Wed, Sep 30
Air France Logo
9:29 am - 8:10 pm
MDW
-
KIN
10h 41m
2 stops
Air France Logo
9:10 am - 4:15 pm
KIN
-
MDW
7h 05m
1 stop
$549Air France
Thu, Sep 24 - Wed, Sep 30

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Southwest flights from Chicago Midway Airport to Jamaica

Our best Southwest deals on Chicago Midway Airport to Jamaica flight tickets
Southwest
Sep 22
MDW6:30 amChicago Midway
6h 25m
1 stop
MBJ12:55 pmMontego Bay Sangster Intl
Sep 29
MBJ1:55 pmMontego Bay Sangster Intl
6h 55m
1 stop
MDW8:50 pmChicago Midway
$442
Southwest
Sep 19
MDW5:55 amChicago Midway
6h 30m
1 stop
MBJ12:25 pmMontego Bay Sangster Intl
Sep 23
MBJ1:55 pmMontego Bay Sangster Intl
6h 55m
1 stop
MDW8:50 pmChicago Midway
$444
Southwest
Sep 13
MDW7:10 amChicago Midway
7h 15m
1 stop
MBJ2:25 pmMontego Bay Sangster Intl
Sep 20
MBJ12:45 pmMontego Bay Sangster Intl
9h 45m
1 stop
MDW10:30 pmChicago Midway
$480

Delta flights from Chicago Midway Airport to Jamaica

Our best Delta deals on Chicago Midway Airport to Jamaica flight tickets
Delta
Dec 5
MDW6:44 pmChicago Midway
17h 11m
2 stops
MBJ12:55 pmMontego Bay Sangster Intl
Dec 11
MBJ2:20 pmMontego Bay Sangster Intl
9h 36m
1 stop
MDW10:56 pmChicago Midway
$447
Delta
Aug 22
MDW6:11 amChicago Midway
9h 23m
1 stop
MBJ3:34 pmMontego Bay Sangster Intl
Aug 27
MBJ4:59 pmMontego Bay Sangster Intl
16h 18m
2 stops
MDW9:17 amChicago Midway
$485
Delta
Oct 24
MDW6:04 amChicago Midway
5h 47m
1 stop
MBJ11:51 amMontego Bay Sangster Intl
Oct 28
MBJ2:26 pmMontego Bay Sangster Intl
8h 07m
1 stop
MDW10:33 pmChicago Midway
$508

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 August 3, 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

Fri 12/4

6:00 am-4:35 pm

1 stop9h 35m

Montego Bay Sangster Intl

Wed 12/9

2:20 pm-10:56 pm

1 stop9h 36m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 11/9

6:00 am-4:35 pm

1 stop9h 35m

Montego Bay Sangster Intl

Fri 11/13

3:40 pm-10:56 pm

1 stop8h 16m

$442
Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 8/29

5:55 am-12:25 pm

1 stop6h 30m

Montego Bay Sangster Intl

Wed 9/2

1:55 pm-8:45 pm

1 stop6h 50m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 9/13

7:10 am-2:25 pm

1 stop7h 15m

Montego Bay Sangster Intl

Wed 9/16

12:55 pm-9:00 pm

1 stop8h 05m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 12/5

6:00 am-4:35 pm

1 stop9h 35m

Montego Bay Sangster Intl

Thu 12/10

2:20 pm-10:56 pm

1 stop9h 36m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 10/28

5:45 am-11:50 am

1 stop6h 05m

Montego Bay Sangster Intl

Mon 11/2

1:00 pm-11:05 pm

1 stop11h 05m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 9/14

6:25 am-2:27 pm

1 stop8h 02m

Montego Bay Sangster Intl

Mon 9/21

3:42 pm-11:44 pm

1 stop8h 02m

$481

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 9/13

6:25 am-2:27 pm

1 stop8h 02m

Montego Bay Sangster Intl

Sun 9/20

3:42 pm-11:44 pm

1 stop8h 02m

$482

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 9/24

9:29 am-8:10 pm

2 stops10h 41m

Kingston Norman Manley

Wed 9/30

9:10 am-6:33 pm

2 stops9h 23m

$547

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 9/24

9:29 am-8:10 pm

2 stops10h 41m

Kingston Norman Manley

Wed 9/30

9:10 am-4:15 pm

1 stop7h 05m

$549

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 December. Flight prices, which tend to average around $493, 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 December, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $522.

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 Saturday when prices can be found for as low as $556. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday 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 $660.

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 Airport to Jamaica flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport 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 55m

Direct flights

Sun

Airports in Jamaica

11 airports
The fastest flight from Chicago Midway Airport to Jamaica takes 3h 55m
Direct flights go from Chicago Midway Airport to Jamaica on 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

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 $172Free CancellationRating
5.6
2,737 reviews
Search Frontier flights
DeltaPriceFrom $395Free CancellationRating
7.8
8,482 reviews
Search Delta flights
SouthwestPriceFrom $467Free CancellationRating
8.0
4,224 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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