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Cheap flights from Chicago Midway Airport to Jamaica from $135

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 2/10. 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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Find the cheapest flights from Chicago Midway Airport to Jamaica

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to Jamaica that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago Midway Airport to Jamaica.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to Jamaica? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Jamaica, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to Jamaica

Find recent round-trip train or bus tickets from Chicago Midway Airport to Jamaica.

All round-trip flight deals to Jamaica

The cheapest plane tickets to Jamaica found on KAYAK recently.
6:44 pm - 11:18 amMDW-MBJ
16h 34m1 stop
12:38 pm - 11:55 pmMBJ-MDW
11h 17m1 stop
$362Frontier
Find Deal
Fri, May 9 - Sat, May 17
7:30 am - 10:38 amMDW-MBJ
26h 08m1 stop
11:44 am - 6:26 pmMBJ-MDW
7h 42m1 stop
$368Frontier
Find Deal
Sat, Jan 25 - Thu, Jan 30
6:48 pm - 1:43 pmMDW-MBJ
17h 55m2 stops
2:48 pm - 7:32 amMBJ-MDW
17h 44m2 stops
Mon, Feb 24 - Mon, Mar 3
6:44 pm - 11:18 amMDW-MBJ
16h 34m1 stop
12:38 pm - 11:55 pmMBJ-MDW
11h 17m1 stop
$371Frontier
Find Deal
Fri, May 2 - Sat, May 10
8:01 pm - 10:34 amMDW-MBJ
13h 33m1 stop
11:48 am - 9:32 pmMBJ-MDW
10h 44m1 stop
$379Frontier
Find Deal
Wed, Feb 5 - Sun, Feb 9
6:00 am - 12:47 pmMDW-MBJ
5h 47m1 stop
8:00 am - 4:20 pmMBJ-MDW
9h 20m1 stop
$383Delta
Find Deal
Tue, Feb 11 - Wed, Feb 26
12:44 pm - 8:52 pmMDW-MBJ
7h 08m1 stop
8:00 am - 6:11 pmMBJ-MDW
11h 11m2 stops
$387Delta
Find Deal
Tue, Feb 25 - Tue, Mar 4
6:44 pm - 11:18 amMDW-MBJ
16h 34m1 stop
12:46 pm - 11:55 pmMBJ-MDW
11h 09m2 stops
Fri, May 2 - Wed, May 7
8:00 am - 12:00 pmMDW-MBJ
4h 00mnonstop
1:00 pm - 5:15 pmMBJ-MDW
4h 15mnonstop
$466Southwest
Find Deal
Tue, Mar 11 - Tue, Mar 18
5:35 am - 12:00 pmMDW-MBJ
6h 25m1 stop
1:00 pm - 5:15 pmMBJ-MDW
4h 15mnonstop
$471Southwest
Find Deal
Tue, Mar 11 - Tue, Mar 18
6:15 am - 12:10 pmMDW-MBJ
28h 55m2 stops
Mon, Feb 10
6:48 pm - 2:53 pmMDW-MBJ
19h 05m1 stop
$149Frontier
Find Deal
Fri, Feb 28
8:47 am - 1:43 pmMDW-MBJ
27h 56m2 stops
Tue, Feb 18
6:44 pm - 11:18 amMDW-MBJ
16h 34m1 stop
$153Frontier
Find Deal
Fri, May 2
9:25 am - 8:37 pmMDW-MBJ
11h 12m2 stops
$168Delta
Find Deal
Tue, Mar 11
5:40 am - 12:20 pmMDW-MBJ
6h 40m1 stop
$217Southwest
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Sun, Apr 6
9:33 am - 8:52 pmMDW-MBJ
10h 19m2 stops
$230Delta
Find Deal
Sat, Mar 8
8:25 am - 1:20 pmMDW-MBJ
3h 55mnonstop
$237Southwest
Find Deal
Sat, Feb 8
10:25 am - 12:48 pmMDW-MBJ
26h 23m3 stops
$385WestJet
Find Deal
Wed, Mar 26
11:22 am - 6:23 pmMDW-MBJ
31h 01m3 stops
$406WestJet
Find Deal
Sat, Mar 15
9:34 am - 8:52 pmMDW-MBJ
10h 18m2 stops
8:00 am - 4:21 pmMBJ-MDW
9h 21m1 stop
$535Delta
Find Deal
Sat, Jan 11 - Tue, Jan 14
8:25 am - 1:20 pmMDW-MBJ
3h 55mnonstop
3:10 pm - 9:25 pmMBJ-MDW
7h 15m1 stop
$629Southwest
Find Deal
Sat, Jan 11 - Tue, Jan 14
5:35 am - 12:45 pmMDW-MBJ
6h 10m1 stop
1:45 pm - 9:45 pmMBJ-MDW
9h 00m1 stop
$649Southwest
Find Deal
Mon, Jan 13 - Wed, Jan 15
5:45 am - 1:30 pmMDW-MBJ
6h 45m1 stop
3:10 pm - 9:25 pmMBJ-MDW
7h 15m1 stop
$672Southwest
Find Deal
Sat, Jan 11 - Tue, Jan 14
6:52 pm - 10:34 amMDW-MBJ
14h 42m1 stop
11:48 am - 9:32 pmMBJ-MDW
10h 44m1 stop
$701Frontier
Find Deal
Wed, Jan 15 - Sun, Jan 19
5:35 am - 12:45 pmMDW-MBJ
6h 10m1 stop
1:45 pm - 10:25 pmMBJ-MDW
9h 40m2 stops
$736Southwest
Find Deal
Mon, Jan 13 - Wed, Jan 15
9:34 am - 8:00 pmMDW-KIN
9h 26m2 stops
9:00 am - 6:14 pmKIN-MDW
10h 14m2 stops
$811Delta
Find Deal
Sat, Jan 11 - Tue, Jan 14
5:35 am - 12:45 pmMDW-MBJ
6h 10m1 stop
3:10 pm - 9:25 pmMBJ-MDW
7h 15m1 stop
$817Southwest
Find Deal
Tue, Jan 14 - Sun, Jan 19
9:34 am - 8:00 pmMDW-KIN
9h 26m2 stops
9:00 am - 4:21 pmKIN-MDW
8h 21m1 stop
$824Delta
Find Deal
Sat, Jan 11 - Tue, Jan 14
5:35 am - 12:45 pmMDW-MBJ
6h 10m1 stop
1:45 pm - 10:25 pmMBJ-MDW
9h 40m2 stops
$861Southwest
Find Deal
Wed, Jan 15 - Sun, Jan 19
8:00 am - 12:00 pmMDW-MBJ
4h 00mnonstop
1:00 pm - 5:15 pmMBJ-MDW
4h 15mnonstop
$466Southwest
Find Deal
Tue, Mar 11 - Tue, Mar 18
8:00 am - 12:00 pmMDW-MBJ
4h 00mnonstop
1:00 pm - 5:15 pmMBJ-MDW
4h 15mnonstop
$549Southwest
Find Deal
Thu, Mar 13 - Thu, Mar 20
8:25 am - 1:20 pmMDW-MBJ
3h 55mnonstop
2:10 pm - 5:25 pmMBJ-MDW
4h 15mnonstop
$561Southwest
Find Deal
Sat, Feb 8 - Sat, Feb 15
8:25 am - 1:20 pmMDW-MBJ
3h 55mnonstop
2:10 pm - 5:25 pmMBJ-MDW
4h 15mnonstop
$677Southwest
Find Deal
Sat, Feb 22 - Sat, Mar 1
8:25 am - 1:20 pmMDW-MBJ
3h 55mnonstop
2:10 pm - 5:25 pmMBJ-MDW
4h 15mnonstop
$822Southwest
Find Deal
Sat, Feb 15 - Sat, Feb 22
8:00 am - 12:00 pmMDW-MBJ
4h 00mnonstop
1:00 pm - 5:15 pmMBJ-MDW
4h 15mnonstop
$865Southwest
Find Deal
Tue, Mar 25 - Sun, Mar 30
9:00 am - 1:00 pmMDW-MBJ
4h 00mnonstop
2:30 pm - 6:35 pmMBJ-MDW
4h 05mnonstop
$1,208Southwest
Find Deal
Thu, Jun 12 - Sun, Jun 15
8:00 am - 12:00 pmMDW-MBJ
4h 00mnonstop
3:25 pm - 7:40 pmMBJ-MDW
4h 15mnonstop
$1,210Southwest
Find Deal
Tue, Mar 25 - Sat, Mar 29
9:00 am - 1:00 pmMDW-MBJ
4h 00mnonstop
2:20 pm - 6:30 pmMBJ-MDW
4h 10mnonstop
$1,298Southwest
Find Deal
Wed, Jun 11 - Tue, Jun 17
9:00 am - 1:00 pmMDW-MBJ
4h 00mnonstop
3:00 pm - 7:10 pmMBJ-MDW
4h 10mnonstop
$1,454Southwest
Find Deal
Tue, Jun 17 - Sat, Jun 21

Southwest flights from Chicago Midway Airport to Jamaica

Our best Southwest deals on Chicago Midway Airport to Jamaica flight tickets
Southwest
Mar 11
MDW8:00 amChicago Midway
4h 00m
MBJ12:00 pmMontego Bay Sangster Intl
Mar 18
MBJ1:00 pmMontego Bay Sangster Intl
4h 15m
MDW5:15 pmChicago Midway
Southwest
Mar 11
MDW5:35 amChicago Midway
6h 25m
1 stop
MBJ12:00 pmMontego Bay Sangster Intl
Mar 18
MBJ1:00 pmMontego Bay Sangster Intl
4h 15m
MDW5:15 pmChicago Midway
Southwest
Mar 10
MDW5:55 amChicago Midway
5h 50m
1 stop
MBJ11:45 amMontego Bay Sangster Intl
Mar 14
MBJ1:00 pmMontego Bay Sangster Intl
10h 15m
1 stop
MDW11:15 pmChicago Midway

Delta flights from Chicago Midway Airport to Jamaica

Our best Delta deals on Chicago Midway Airport to Jamaica flight tickets
Delta
Feb 11
MDW6:00 amChicago Midway
5h 47m
1 stop
MBJ12:47 pmMontego Bay Sangster Intl
Feb 26
MBJ8:00 amMontego Bay Sangster Intl
9h 20m
1 stop
MDW4:20 pmChicago Midway
Delta
Feb 25
MDW12:44 pmChicago Midway
7h 08m
1 stop
MBJ8:52 pmMontego Bay Sangster Intl
Mar 4
MBJ8:00 amMontego Bay Sangster Intl
11h 11m
2 stops
MDW6:11 pmChicago Midway
Delta
Feb 21
MDW12:44 pmChicago Midway
7h 08m
1 stop
MBJ8:52 pmMontego Bay Sangster Intl
Feb 27
MBJ12:36 pmMontego Bay Sangster Intl
10h 44m
1 stop
MDW10:20 pmChicago Midway

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 April. Flight prices, which tend to average around $522, 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 April, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $571.

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 Tuesday when prices can be found for as low as $502. 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 $929.

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 are 1 cabin classes 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.

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

$135

Fastest flight time

3h 55m

Direct flights

Mon, Wed, Thu, Fri and Sun

Airports in Jamaica

2 airports
The best one-way flight to Jamaica from Chicago Midway Airport in the past 72 hours is $135. The best round-trip flight deal from Chicago Midway Airport to Jamaica found on momondo in the last 72 hours is $362.
The fastest flight from Chicago Midway Airport to Jamaica takes 3h 55m
Direct flights go from Chicago Midway Airport to Jamaica on Monday, Wednesday, Thursday, Friday and Sunday. The only airline offering direct flights is Southwest.
There are 2 airports near Jamaica: Kingston Norman Manley (KIN), Montego Bay Sangster Intl (MBJ)

  • 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
DeltaPriceFrom $458Free CancellationRating
8.0
8,501 reviews
Search Delta flights
SouthwestPriceFrom $579Free CancellationRating
8.1
4,650 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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