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Cheap flights from Chicago Midway Airport to Jamaica from $132

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 2/20. 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
6:45 am - 3:20 pm
MDW
-
MBJ
7h 35m1 stop
Delta Logo
4:45 pm - 10:22 pm
MBJ
-
MDW
6h 37m1 stop
$435Delta
dom., ene. 18 - mié., ene. 21
Delta Logo
6:20 pm - 12:32 pm
MDW
-
MBJ
17h 12m2 stops
Delta Logo
4:44 pm - 12:46 pm
MBJ
-
MDW
21h 02m2 stops
$440Delta
vie., feb. 27 - jue., mar. 5
Frontier Logo
9:04 pm - 9:00 am
MDW
-
MBJ
10h 56m1 stop
Frontier Logo
10:40 am - 9:33 pm
MBJ
-
MDW
11h 53m1 stop
$443Frontier
dom., feb. 15 - sáb., feb. 21
Delta Logo
6:00 am - 8:00 pm
MDW
-
KIN
13h 00m1 stop
Delta Logo
9:00 am - 10:22 pm
KIN
-
MDW
14h 22m1 stop
$445Delta
vie., ene. 23 - sáb., ene. 31
Delta Logo
6:20 pm - 8:00 pm
MDW
-
KIN
24h 40m2 stops
Delta Logo
9:00 am - 8:53 am
KIN
-
MDW
23h 53m2 stops
$450Delta
mar., mar. 3 - lun., mar. 9
Multiple Airlines Logo
6:12 am - 8:59 am
MDW
-
MBJ
25h 47m1 stop
Multiple Airlines Logo
12:57 pm - 10:27 pm
MBJ
-
MDW
34h 30m2 stops
$456Multiple Airlines
jue., ene. 1 - vie., ene. 9
Southwest Logo
6:50 am - 2:10 pm
MDW
-
MBJ
6h 20m1 stop
Southwest Logo
2:00 pm - 9:00 pm
MBJ
-
MDW
8h 00m1 stop
$463Southwest
mié., feb. 18 - mié., feb. 25
Southwest Logo
6:50 am - 2:10 pm
MDW
-
MBJ
6h 20m1 stop
Southwest Logo
2:00 pm - 10:05 pm
MBJ
-
MDW
9h 05m2 stops
$468Southwest
mié., feb. 18 - mié., feb. 25
Southwest Logo
7:55 pm - 1:00 pm
MDW
-
MBJ
16h 05m2 stops
Southwest Logo
2:00 pm - 9:00 pm
MBJ
-
MDW
8h 00m1 stop
$478Southwest
mar., ene. 20 - mar., ene. 27
Multiple Airlines Logo
9:04 pm - 12:15 pm
MDW
-
KIN
14h 11m2 stops
Multiple Airlines Logo
3:30 pm - 2:20 pm
KIN
-
MDW
23h 50m1 stop
$593Multiple Airlines
dom., mar. 1 - sáb., mar. 7

Southwest flights from Chicago Midway Airport to Jamaica

Our best Southwest deals on Chicago Midway Airport to Jamaica flight tickets
Southwest
Feb 18
MDW6:50 amChicago Midway
6h 20m
1 stop
MBJ2:10 pmMontego Bay Sangster Intl
Feb 25
MBJ2:00 pmMontego Bay Sangster Intl
8h 00m
1 stop
MDW9:00 pmChicago Midway
$463
Find similar
Southwest
Feb 18
MDW6:50 amChicago Midway
6h 20m
1 stop
MBJ2:10 pmMontego Bay Sangster Intl
Feb 25
MBJ2:00 pmMontego Bay Sangster Intl
9h 05m
2 stops
MDW10:05 pmChicago Midway
$468
Find similar
Southwest
Apr 6
MDW9:40 pmChicago Midway
13h 55m
2 stops
MBJ11:35 amMontego Bay Sangster Intl
Apr 10
MBJ2:25 pmMontego Bay Sangster Intl
9h 15m
1 stop
MDW11:40 pmChicago Midway
$471
Find similar

Delta flights from Chicago Midway Airport to Jamaica

Our best Delta deals on Chicago Midway Airport to Jamaica flight tickets
Delta
Jan 27
MDW6:00 amChicago Midway
8h 20m
1 stop
MBJ3:20 pmMontego Bay Sangster Intl
Jan 31
MBJ4:45 pmMontego Bay Sangster Intl
6h 37m
1 stop
MDW10:22 pmChicago Midway
$435
Find similar
Delta
Feb 27
MDW6:00 amChicago Midway
8h 19m
1 stop
MBJ3:19 pmMontego Bay Sangster Intl
Mar 5
MBJ4:44 pmMontego Bay Sangster Intl
21h 02m
2 stops
MDW12:46 pmChicago Midway
$440
Find similar
Delta
Jan 23
MDW6:00 amChicago Midway
13h 00m
1 stop
KIN8:00 pmKingston Norman Manley
Jan 31
KIN9:00 amKingston Norman Manley
14h 22m
1 stop
MDW10:22 pmChicago Midway
$445
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 diciembre 23, 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

dom. 1/18

6:45 am-3:20 pm

1 stop7h 35m

Montego Bay Sangster Intl

mié. 1/21

4:45 pm-10:22 pm

1 stop6h 37m

$435

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

vie. 2/27

6:20 pm-12:32 pm

2 stops17h 12m

Montego Bay Sangster Intl

jue. 3/5

4:44 pm-12:46 pm

2 stops21h 02m

$440

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 2/15

9:04 pm-9:00 am

1 stop10h 56m

Montego Bay Sangster Intl

sáb. 2/21

10:40 am-9:33 pm

1 stop11h 53m

$443

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

vie. 1/23

6:00 am-8:00 pm

1 stop13h 00m

Kingston Norman Manley

sáb. 1/31

9:00 am-10:22 pm

1 stop14h 22m

$445

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

mar. 3/3

6:20 pm-8:00 pm

2 stops24h 40m

Kingston Norman Manley

lun. 3/9

9:00 am-8:53 am

2 stops23h 53m

$450

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

jue. 1/1

6:12 am-8:59 am

1 stop25h 47m

Montego Bay Sangster Intl

vie. 1/9

12:57 pm-10:27 pm

2 stops34h 30m

$456

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mié. 2/18

6:50 am-2:10 pm

1 stop6h 20m

Montego Bay Sangster Intl

mié. 2/25

2:00 pm-9:00 pm

1 stop8h 00m

$463

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mié. 2/18

6:50 am-2:10 pm

1 stop6h 20m

Montego Bay Sangster Intl

mié. 2/25

2:00 pm-10:05 pm

2 stops9h 05m

$468

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar. 1/20

7:55 pm-1:00 pm

2 stops16h 05m

Montego Bay Sangster Intl

mar. 1/27

2:00 pm-9:00 pm

1 stop8h 00m

$478

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

dom. 3/1

9:04 pm-12:15 pm

2 stops14h 11m

Kingston Norman Manley

sáb. 3/7

3:30 pm-2:20 pm

1 stop23h 50m

$593

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 July is also cheap. Prices for this month can be found on momondo for an average of $622.

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 $724 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?

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

Best Price Found

$459

Fastest flight time

3h 50m

Direct flights

Mon, Wed and Sun

Airports in Jamaica

11 airports
The best flight deal from Chicago Midway Airport to Jamaica found on momondo in the last 72 hours is $459
The fastest flight from Chicago Midway Airport to Jamaica takes 3h 50m
Direct flights go from Chicago Midway Airport to Jamaica on Monday, Wednesday 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
5.8
3,075 reviews
Search Frontier flights
DeltaPriceFrom $395Free CancellationRating
7.9
8,014 reviews
Search Delta flights
SouthwestPriceFrom $549Free CancellationRating
8.0
4,253 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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