Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Jamaica from $134

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 1/31. 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

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

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.
7:15 am - 10:38 amMDW-MBJ
26h 23m1 stop
2:20 pm - 11:29 pmMBJ-MDW
10h 09m1 stop
$336Frontier
Find Deal
Sat, Jan 11 - Sat, Jan 18
8:01 pm - 10:34 amMDW-MBJ
13h 33m1 stop
11:48 am - 9:32 pmMBJ-MDW
10h 44m1 stop
$360Frontier
Find Deal
Wed, Jan 22 - Sun, Jan 26
10:58 am - 1:33 pmMDW-MBJ
25h 35m2 stops
2:17 pm - 11:42 amMBJ-MDW
22h 25m1 stop
Sun, Dec 8 - Tue, Dec 10
10:58 am - 1:33 pmMDW-MBJ
25h 35m2 stops
10:04 am - 5:18 pmMBJ-MDW
8h 14m1 stop
Sun, Dec 8 - Thu, Dec 12
6:00 am - 1:03 pmMDW-MBJ
6h 03m1 stop
4:49 pm - 10:20 pmMBJ-MDW
6h 31m1 stop
$469Delta
Find Deal
Tue, Dec 31 - Wed, Jan 22
12:10 pm - 8:51 pmMDW-MBJ
7h 41m1 stop
8:00 am - 6:14 pmMBJ-MDW
11h 14m2 stops
$474Delta
Find Deal
Sun, Jan 5 - Fri, Jan 10
8:25 am - 1:20 pmMDW-MBJ
3h 55mnonstop
2:10 pm - 5:25 pmMBJ-MDW
4h 15mnonstop
$505Southwest
Find Deal
Sat, Jan 11 - Sat, Jan 18
6:35 am - 2:50 pmMDW-MBJ
7h 15m1 stop
2:10 pm - 5:25 pmMBJ-MDW
4h 15mnonstop
$532Southwest
Find Deal
Sat, Jan 11 - Sat, Jan 18
7:14 pm - 3:41 pmMDW-KIN
43h 27m2 stops
4:35 pm - 1:31 pmKIN-MDW
21h 56m2 stops
$3,568WestJet
Find Deal
Sat, Dec 7 - Tue, Dec 10
12:10 pm - 3:41 pmMDW-KIN
50h 31m2 stops
4:35 pm - 5:11 pmKIN-MDW
25h 36m2 stops
$3,928WestJet
Find Deal
Sat, Dec 21 - Mon, Dec 30
12:51 pm - 1:10 pmMDW-MBJ
23h 19m1 stop
$134Frontier
Find Deal
Fri, Jan 31
7:35 am - 10:38 amMDW-MBJ
26h 03m1 stop
$136Frontier
Find Deal
Sat, Jan 11
4:35 pm - 1:37 pmMDW-MBJ
20h 02m3 stops
Mon, Jan 13
4:01 pm - 1:45 pmMDW-MBJ
20h 44m2 stops
Fri, Jan 3
6:00 am - 3:24 pmMDW-MBJ
8h 24m1 stop
$211Delta
Find Deal
Sun, Jan 19
8:35 pm - 12:45 pmMDW-MBJ
15h 10m2 stops
$217Southwest
Find Deal
Mon, Feb 17
8:25 am - 1:20 pmMDW-MBJ
3h 55mnonstop
$232Southwest
Find Deal
Sat, Jan 11
6:00 am - 2:48 pmMDW-MBJ
7h 48m1 stop
$236Delta
Find Deal
Sat, Jan 4
10:19 am - 1:48 pmMDW-MBJ
26h 29m3 stops
$429WestJet
Find Deal
Tue, Feb 18
10:19 am - 1:48 pmMDW-MBJ
26h 29m3 stops
$430WestJet
Find Deal
Tue, Feb 18
7:55 pm - 12:45 pmMDW-MBJ
15h 50m2 stops
1:45 pm - 11:40 pmMBJ-MDW
10h 55m2 stops
$702Southwest
Find Deal
Mon, Nov 25 - Wed, Nov 27
5:10 am - 12:45 pmMDW-MBJ
6h 35m1 stop
2:00 pm - 11:15 pmMBJ-MDW
10h 15m1 stop
$743Southwest
Find Deal
Mon, Nov 25 - Wed, Nov 27
6:05 am - 4:30 pmMDW-MBJ
9h 25m1 stop
2:17 pm - 11:42 amMBJ-MDW
22h 25m1 stop
$745Frontier
Find Deal
Tue, Nov 26 - Tue, Dec 3
7:55 pm - 12:45 pmMDW-MBJ
15h 50m2 stops
1:45 pm - 10:20 pmMBJ-MDW
9h 35m2 stops
$775Southwest
Find Deal
Mon, Nov 25 - Fri, Nov 29
6:30 am - 2:50 pmMDW-MBJ
7h 20m1 stop
2:00 pm - 9:15 pmMBJ-MDW
8h 15m1 stop
$816Southwest
Find Deal
Mon, Nov 25 - Fri, Nov 29
9:00 am - 1:33 pmMDW-MBJ
27h 33m2 stops
1:22 pm - 11:58 pmMBJ-MDW
11h 36m1 stop
Sun, Nov 24 - Sun, Dec 1
6:00 am - 2:07 pmMDW-MBJ
7h 07m1 stop
3:32 pm - 9:46 pmMBJ-MDW
7h 14m1 stop
$962Delta
Find Deal
Fri, Nov 22 - Mon, Dec 2
11:15 am - 1:45 pmMDW-MBJ
25h 30m2 stops
2:45 pm - 1:37 pmMBJ-MDW
23h 52m3 stops
$1,253
Find Deal
Sun, Nov 24 - Fri, Nov 29
6:00 am - 4:33 pmMDW-MBJ
9h 33m1 stop
2:06 pm - 9:46 pmMBJ-MDW
8h 40m1 stop
$1,982Delta
Find Deal
Sun, Nov 24 - Sun, Dec 1
7:17 pm - 1:53 pmMDW-MBJ
41h 36m2 stops
2:55 pm - 1:35 pmMBJ-MDW
23h 40m2 stops
$3,577WestJet
Find Deal
Tue, Nov 26 - Tue, Dec 3
8:25 am - 1:20 pmMDW-MBJ
3h 55mnonstop
2:10 pm - 5:25 pmMBJ-MDW
4h 15mnonstop
$505Southwest
Find Deal
Sat, Jan 11 - Sat, Jan 18
9:40 am - 1:40 pmMDW-MBJ
4h 00mnonstop
2:40 pm - 6:55 pmMBJ-MDW
4h 15mnonstop
$621Southwest
Find Deal
Sat, Apr 12 - Sat, Apr 19
9:30 am - 1:30 pmMDW-MBJ
4h 00mnonstop
2:40 pm - 6:55 pmMBJ-MDW
4h 15mnonstop
$641Southwest
Find Deal
Sat, Apr 5 - Sat, Apr 12
9:30 am - 2:30 pmMDW-MBJ
4h 00mnonstop
3:25 pm - 7:40 pmMBJ-MDW
4h 15mnonstop
$801Southwest
Find Deal
Sat, Mar 8 - Sat, Mar 15
9:30 am - 2:30 pmMDW-MBJ
4h 00mnonstop
3:25 pm - 7:40 pmMBJ-MDW
4h 15mnonstop
$927Southwest
Find Deal
Sat, Mar 8 - Sat, Mar 15
8:00 am - 12:00 pmMDW-MBJ
4h 00mnonstop
3:25 pm - 7:40 pmMBJ-MDW
4h 15mnonstop
$1,006Southwest
Find Deal
Tue, Mar 18 - Sat, Mar 22

Frontier flights from Chicago Midway Airport to Jamaica

Our best Frontier deals on Chicago Midway Airport to Jamaica flight tickets
Frontier
Jan 11
MDW7:15 amChicago Midway
26h 23m
1 stop
MBJ10:38 amMontego Bay Sangster Intl
Jan 18
MBJ2:20 pmMontego Bay Sangster Intl
10h 09m
1 stop
MDW11:29 pmChicago Midway
Frontier
Jan 22
MDW8:01 pmChicago Midway
13h 33m
1 stop
MBJ10:34 amMontego Bay Sangster Intl
Jan 26
MBJ11:48 amMontego Bay Sangster Intl
10h 44m
1 stop
MDW9:32 pmChicago Midway
Frontier
Jan 8
MDW6:52 pmChicago Midway
14h 42m
1 stop
MBJ10:34 amMontego Bay Sangster Intl
Jan 12
MBJ11:48 amMontego Bay Sangster Intl
28h 45m
1 stop
MDW3:33 pmChicago Midway

Delta flights from Chicago Midway Airport to Jamaica

Our best Delta deals on Chicago Midway Airport to Jamaica flight tickets
Delta
Dec 31
MDW6:00 amChicago Midway
6h 03m
1 stop
MBJ1:03 pmMontego Bay Sangster Intl
Jan 22
MBJ4:49 pmMontego Bay Sangster Intl
6h 31m
1 stop
MDW10:20 pmChicago Midway
Delta
Jan 5
MDW12:10 pmChicago Midway
7h 41m
1 stop
MBJ8:51 pmMontego Bay Sangster Intl
Jan 10
MBJ8:00 amMontego Bay Sangster Intl
11h 14m
2 stops
MDW6:14 pmChicago Midway
Delta
Jan 19
MDW9:34 amChicago Midway
10h 18m
2 stops
MBJ8:52 pmMontego Bay Sangster Intl
Jan 24
MBJ8:00 amMontego Bay Sangster Intl
11h 14m
2 stops
MDW6:14 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 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 $487. This is often the case because there is less demand to fly during this day of the week. On the other hand, Thursday 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 $800.

Can stopping save me money on Chicago Midway Airport to Jamaica flights?

You could potentially save up to 41% 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

$134

Fastest flight time

3h 55m

Direct flights

Mon, Wed, 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 $134. The best round-trip flight deal from Chicago Midway Airport to Jamaica found on momondo in the last 72 hours is $336.
The fastest flight from Chicago Midway Airport to Jamaica takes 3h 55m
Direct flights go from Chicago Midway Airport to Jamaica on Monday, Wednesday, 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
FrontierPriceFrom $242Free CancellationRating
6.1
3,536 reviews
Search Frontier flights
DeltaPriceFrom $375Free CancellationRating
8.0
8,755 reviews
Search Delta flights
SouthwestPriceFrom $598Free CancellationRating
8.1
5,005 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.


An easier way to manage your Jamaica trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Tue 11/26
Tue 12/3
Email me momondo's favorite deals

Find better results for your trip to Jamaica

Popular cities in Jamaica

Popular flights according to clicks in the last 7 days on momondo