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Cheap flights from Chicago Midway Airport to Jamaica from $175

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.
Frontier Logo
6:40 pm - 2:33 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
19h 53m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
3:48 pm - 11:43 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
7h 55m1 stop Atlanta Hartsfield-Jackson
$433Frontier
Thu, Oct 22 - Mon, Oct 26
Frontier Logo
6:40 pm - 2:33 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
19h 53m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
3:48 pm - 11:43 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
7h 55m1 stop Atlanta Hartsfield-Jackson
$433Frontier
Thu, Oct 22 - Sat, Oct 24
Frontier Logo
3:50 pm - 1:17 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
20h 27m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
2:22 pm - 11:33 amMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
22h 11m1 stop Atlanta Hartsfield-Jackson
$441Frontier
Thu, Dec 10 - Mon, Dec 14
Southwest Logo
5:20 am - 12:50 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
6h 30m1 stop Orlando
Southwest Logo
3:25 pm - 9:25 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
7h 00m1 stop Baltimore/Washington
$482Southwest
Tue, Dec 8 - Tue, Dec 15
Southwest Logo
5:45 am - 11:50 amMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
6h 05m1 stop Orlando
Southwest Logo
3:25 pm - 9:25 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
7h 00m1 stop Baltimore/Washington
$482Southwest
Tue, Oct 27 - Tue, Nov 3
Delta Logo
6:00 am - 4:57 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
9h 57m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:28 pm - 10:54 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 26m1 stop Atlanta Hartsfield-Jackson
$482Delta
Tue, Nov 10 - Fri, Nov 13
Delta Logo
6:00 am - 4:57 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
9h 57m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:16 pm - 10:54 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
9h 38m1 stop Atlanta Hartsfield-Jackson
$482Delta
Tue, Nov 10 - Thu, Nov 12
Southwest Logo
5:20 am - 2:45 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 25m1 stop Orlando
Southwest Logo
1:50 pm - 10:40 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
9h 50m2 stops Orlando Nashville Intl
$487Southwest
Tue, Dec 8 - Tue, Dec 15
Multiple Airlines Logo
5:20 pm - 1:08 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
18h 48m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
1:45 pm - 11:46 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
35h 01m2 stops Tampa Atlanta Hartsfield-Jackson
$625Multiple Airlines
Sat, Jan 2 - Sat, Jan 9
Multiple Airlines Logo
1:18 pm - 12:45 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
22h 27m2 stops Atlanta Hartsfield-Jackson Tampa
Multiple Airlines Logo
2:01 pm - 11:46 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
10h 45m1 stop Atlanta Hartsfield-Jackson
$666Multiple Airlines
Tue, Jan 5 - Sat, Jan 9

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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
Dec 1
MDW6:00 amChicago Midway
7h 25m
1 stop
MBJ2:25 pmMontego Bay Sangster Intl
Dec 8
MBJ3:45 pmMontego Bay Sangster Intl
6h 30m
1 stop
MDW9:15 pmChicago Midway
$503
Southwest
Nov 15
MDW5:05 amChicago Midway
8h 20m
1 stop
MBJ2:25 pmMontego Bay Sangster Intl
Nov 20
MBJ1:00 pmMontego Bay Sangster Intl
11h 10m
1 stop
MDW11:10 pmChicago Midway
$512
Southwest
Nov 15
MDW6:30 pmChicago Midway
16h 30m
2 stops
MBJ12:00 pmMontego Bay Sangster Intl
Nov 20
MBJ3:45 pmMontego Bay Sangster Intl
8h 15m
1 stop
MDW11:00 pmChicago Midway
$517

Frontier flights from Chicago Midway Airport to Jamaica

Our best Frontier deals on Chicago Midway Airport to Jamaica flight tickets
Frontier
Oct 22
MDW6:40 pmChicago Midway
19h 53m
1 stop
MBJ2:33 pmMontego Bay Sangster Intl
Oct 26
MBJ3:48 pmMontego Bay Sangster Intl
7h 55m
1 stop
MDW11:43 pmChicago Midway
$433
Frontier
Oct 4
MDW6:25 amChicago Midway
8h 02m
1 stop
MBJ2:27 pmMontego Bay Sangster Intl
Oct 11
MBJ3:48 pmMontego Bay Sangster Intl
7h 55m
1 stop
MDW11:43 pmChicago Midway
$435
Frontier
Dec 10
MDW3:50 pmChicago Midway
20h 27m
1 stop
MBJ1:17 pmMontego Bay Sangster Intl
Dec 14
MBJ2:22 pmMontego Bay Sangster Intl
22h 11m
1 stop
MDW11:33 amChicago Midway
$441

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago Midway Airport to Jamaica that are best for you.

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Route

Depart

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Price

Cheapest round-trip

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Thu 10/22

6:40 pm-2:33 pm

1 stop19h 53m

Montego Bay Sangster Intl

Mon 10/26

3:48 pm-11:43 pm

1 stop7h 55m

$433

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Thu 10/22

6:40 pm-2:33 pm

1 stop19h 53m

Montego Bay Sangster Intl

Sat 10/24

3:48 pm-11:43 pm

1 stop7h 55m

$433

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Thu 12/10

3:50 pm-1:17 pm

1 stop20h 27m

Montego Bay Sangster Intl

Mon 12/14

2:22 pm-11:33 am

1 stop22h 11m

$441

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Tue 12/8

5:20 am-12:50 pm

1 stop6h 30m

Montego Bay Sangster Intl

Tue 12/15

3:25 pm-9:25 pm

1 stop7h 00m

$482
Quickest round-trip

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Tue 10/27

5:45 am-11:50 am

1 stop6h 05m

Montego Bay Sangster Intl

Tue 11/3

3:25 pm-9:25 pm

1 stop7h 00m

$482

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Tue 11/10

6:00 am-4:57 pm

1 stop9h 57m

Montego Bay Sangster Intl

Fri 11/13

3:28 pm-10:54 pm

1 stop8h 26m

$482

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Tue 11/10

6:00 am-4:57 pm

1 stop9h 57m

Montego Bay Sangster Intl

Thu 11/12

2:16 pm-10:54 pm

1 stop9h 38m

$482

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Tue 12/8

5:20 am-2:45 pm

1 stop8h 25m

Montego Bay Sangster Intl

Tue 12/15

1:50 pm-10:40 pm

2 stops9h 50m

$487

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Sat 1/2

5:20 pm-1:08 pm

1 stop18h 48m

Montego Bay Sangster Intl

Sat 1/9

1:45 pm-11:46 pm

2 stops35h 01m

$625

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Tue 1/5

1:18 pm-12:45 pm

2 stops22h 27m

Montego Bay Sangster Intl

Sat 1/9

2:01 pm-11:46 pm

1 stop10h 45m

$666

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 $476, 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 May is also cheap. Prices for this month can be found on momondo for an average of $497.

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 $574. 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

Best Price Found

$175

Fastest flight time

3h 55m

Direct flights

Mon and Sun

Airports in Jamaica

11 airports
The best one-way flight to Jamaica from Chicago Midway Airport in the past 72 hours is $175. The best round-trip flight deal from Chicago Midway Airport to Jamaica found on momondo in the last 72 hours is $433.
The fastest flight from Chicago Midway Airport to Jamaica takes 3h 55m
Direct flights go from Chicago Midway Airport to Jamaica on Monday 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

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
2,567 reviews
Search Frontier flights
DeltaPriceFrom $395Free CancellationRating
7.8
8,608 reviews
Search Delta flights
SouthwestPriceFrom $467Free CancellationRating
8.0
4,204 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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