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Cheap flights from Jamaica to Chicago from $212

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Jamaica to Chicago departing on 9/4. 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 Jamaica to Chicago

Recent round-trip flight deals from Jamaica to Chicago

Frontier Logo
3:45 pm - 11:17 pmMBJ-MDW
7h 32m1 stop
Frontier Logo
11:39 am - 2:40 pmMDW-MBJ
27h 01m1 stop
$376Frontier
Find Deal
Fri, Aug 8 - Tue, Aug 12
Frontier Logo
9:05 am - 10:40 amMBJ-MDW
25h 35m1 stop
Frontier Logo
11:03 am - 7:55 amMDW-MBJ
20h 52m1 stop
$379Frontier
Find Deal
Mon, Aug 4 - Thu, Aug 21
Frontier Logo
9:05 am - 11:17 pmMBJ-MDW
14h 12m1 stop
Frontier Logo
6:15 am - 8:48 amMDW-MBJ
26h 33m1 stop
$385Frontier
Find Deal
Thu, Aug 14 - Fri, Aug 22
Southwest Logo
12:45 pm - 12:05 amMBJ-MDW
11h 20m2 stops
Southwest Logo
6:35 am - 2:00 pmMDW-MBJ
7h 25m1 stop
$473Southwest
Find Deal
Thu, Aug 14 - Fri, Aug 22
Southwest Logo
12:45 pm - 12:05 amMBJ-MDW
11h 20m2 stops
Southwest Logo
6:15 am - 11:55 amMDW-MBJ
5h 40m1 stop
$478Southwest
Find Deal
Fri, Aug 8 - Tue, Aug 12
Delta Logo
2:30 pm - 9:44 pmMBJ-MDW
7h 14m1 stop
Delta Logo
6:00 am - 11:55 amMDW-MBJ
5h 55m1 stop
$542Delta
Find Deal
Tue, Aug 26 - Sun, Aug 31
Delta Logo
2:30 pm - 9:44 pmMBJ-MDW
7h 14m1 stop
Delta Logo
6:00 am - 11:55 amMDW-MBJ
5h 55m1 stop
$645Delta
Find Deal
Tue, Aug 19 - Tue, Aug 26
Logo
7:25 pm - 10:20 amMBJ-MDW
15h 55m2 stops
Logo
6:00 am - 3:33 pmMDW-MBJ
8h 33m1 stop
$692
Find Deal
Sat, Nov 29 - Sun, Dec 7
Logo
12:45 pm - 1:06 pmMBJ-MDW
24h 21m3 stops
Logo
9:15 am - 11:05 amMDW-MBJ
25h 50m2 stops
$1,532
Find Deal
Fri, Aug 8 - Tue, Aug 12
WestJet Logo
10:30 am - 9:36 amMBJ-MDW
23h 06m2 stops
WestJet Logo
1:43 pm - 9:27 amMDW-MBJ
19h 44m2 stops
$3,136WestJet
Find Deal
Tue, Aug 19 - Tue, Aug 26

Frontier flights from Jamaica to Chicago Midway Airport

Our best Frontier deals on Jamaica to Chicago Midway Airport flight tickets
Frontier
Aug 8
MBJ3:45 pmMontego Bay Sangster Intl
7h 32m
1 stop
MDW11:17 pmChicago Midway
Aug 12
MDW11:39 amChicago Midway
27h 01m
1 stop
MBJ2:40 pmMontego Bay Sangster Intl
$376
Find similar
Frontier
Aug 4
MBJ9:05 amMontego Bay Sangster Intl
25h 35m
1 stop
MDW10:40 amChicago Midway
Aug 21
MDW11:03 amChicago Midway
20h 52m
1 stop
MBJ7:55 amMontego Bay Sangster Intl
$379
Find similar
Frontier
Aug 14
MBJ9:05 amMontego Bay Sangster Intl
14h 12m
1 stop
MDW11:17 pmChicago Midway
Aug 22
MDW6:15 amChicago Midway
26h 33m
1 stop
MBJ8:48 amMontego Bay Sangster Intl
$385
Find similar

Southwest flights from Jamaica to Chicago Midway Airport

Our best Southwest deals on Jamaica to Chicago Midway Airport flight tickets
Southwest
Aug 14
MBJ12:45 pmMontego Bay Sangster Intl
11h 20m
2 stops
MDW12:05 amChicago Midway
Aug 22
MDW6:35 amChicago Midway
7h 25m
1 stop
MBJ2:00 pmMontego Bay Sangster Intl
$473
Find similar
Southwest
Aug 8
MBJ12:45 pmMontego Bay Sangster Intl
11h 20m
2 stops
MDW12:05 amChicago Midway
Aug 12
MDW6:15 amChicago Midway
5h 40m
1 stop
MBJ11:55 amMontego Bay Sangster Intl
$478
Find similar
Southwest
Aug 14
MBJ12:45 pmMontego Bay Sangster Intl
11h 20m
2 stops
MDW12:05 amChicago Midway
Aug 22
MDW6:30 amChicago Midway
7h 30m
2 stops
MBJ2:00 pmMontego Bay Sangster Intl
$564
Find similar

See travel insights to Chicago from

How to get the cheapest flight ticket from Jamaica to Chicago Midway Airport

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 Chicago Midway Airport?

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Jamaica. The lowest ticket price found for a Thursday departure recently was $629. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday is the most expensive day to depart from Jamaica because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $743.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Jamaica at noon is the least expensive time of day to depart. momondo users have found prices as low as $568 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $763. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Jamaica to Chicago Midway flight route?

Fly from Montego Bay Sangster Intl to Chicago Midway for the best Jamaica - Chicago Midway flight prices

What cabin class options are available on Jamaica to Chicago Midway flights?

There are 1 cabin classes available to choose from on Jamaica to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Jamaica to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Jamaica to Chicago Midway Airport

Best Price Found

$212

Fastest flight time

4h 10m

Direct flights

Thu, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from Jamaica in the past 72 hours is $212. The best round-trip flight deal from Jamaica to Chicago Midway Airport found on momondo in the last 72 hours is $376.
The fastest flight from Jamaica to Chicago Midway Airport takes 4h 10m
Direct flights go from Jamaica to Chicago Midway Airport on Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is Southwest.
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  • When did momondo last update prices for flights from Jamaica to Chicago Midway Airport?

    Prices for flights from Jamaica to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Jamaica to Chicago Midway Airport?

  • How old do you have to be to fly from Jamaica to Chicago Midway Airport?

    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 Jamaica to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Jamaica to Chicago Midway Airport?

Best airlines flying from Jamaica to Chicago Midway Airport

Compare and see reviews for airlines that fly from Jamaica to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $332Free CancellationRating
8.0
7,952 reviews
Search Delta flights
SouthwestPriceFrom $509Free CancellationRating
8.0
4,250 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Jamaica to Chicago?

Finding the right flight to Chicago from Jamaica is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Jamaica to Chicago with flexible booking policies on momondo?

Flights from Jamaica to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Jamaica to Chicago?

Once all potential Jamaica to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Jamaica to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Jamaica. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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