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Cheap flights from Jamaica to Chicago from $180

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 12/31. 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

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Find the cheapest flights from Jamaica to Chicago

Recent round-trip flight deals from Jamaica to Chicago

Enter your travel dates to find the best prices.
Frontier Logo
3:34 pm - 10:12 pm
MBJ
-
MDW
7h 38m1 stop
Frontier Logo
6:12 am - 2:29 pm
MDW
-
MBJ
7h 17m1 stop
$307Frontier
Sat, Dec 20 - Sat, Jan 3
Frontier Logo
3:34 pm - 10:12 pm
MBJ
-
MDW
7h 38m1 stop
Frontier Logo
6:12 am - 2:29 pm
MDW
-
MBJ
7h 17m1 stop
$331Frontier
Sat, Dec 20 - Thu, Dec 25
Frontier Logo
3:34 pm - 10:12 pm
MBJ
-
MDW
7h 38m1 stop
Frontier Logo
6:12 am - 2:29 pm
MDW
-
MBJ
7h 17m1 stop
$351Frontier
Sat, Dec 20 - Sat, Dec 27
Frontier Logo
3:49 pm - 10:12 pm
MBJ
-
MDW
7h 23m1 stop
Frontier Logo
6:14 am - 2:29 pm
MDW
-
MBJ
7h 15m1 stop
$357Frontier
Wed, Dec 24 - Tue, Dec 30
Delta Logo
8:00 am - 5:26 pm
MBJ
-
MDW
10h 26m2 stops
Delta Logo
9:50 am - 8:41 pm
MDW
-
MBJ
9h 51m1 stop
$362Delta
Wed, Dec 24 - Tue, Dec 30
Frontier Logo
3:34 pm - 9:04 pm
MBJ
-
MDW
30h 30m2 stops
Frontier Logo
6:12 am - 2:29 pm
MDW
-
MBJ
7h 17m1 stop
$366Frontier
Sat, Dec 20 - Thu, Dec 25
Frontier Logo
11:12 am - 10:12 pm
MBJ
-
MDW
12h 00m1 stop
Frontier Logo
7:05 am - 2:54 pm
MDW
-
MBJ
30h 49m2 stops
$405Frontier
Sat, Dec 20 - Sat, Jan 3
Frontier Logo
11:12 am - 10:12 pm
MBJ
-
MDW
12h 00m1 stop
Frontier Logo
7:05 am - 2:54 pm
MDW
-
MBJ
30h 49m2 stops
$406Frontier
Sat, Dec 20 - Sat, Jan 3
Southwest Logo
1:55 pm - 5:05 pm
MBJ
-
MDW
4h 10mnonstop
Southwest Logo
5:30 am - 1:50 pm
MDW
-
MBJ
7h 20m1 stop
$421Southwest
Sat, Dec 20 - Sat, Jan 3
Delta Logo
8:00 am - 4:20 pm
MBJ
-
MDW
9h 20m1 stop
Delta Logo
6:00 am - 8:41 pm
MDW
-
MBJ
13h 41m1 stop
$434Delta
Sun, Dec 21 - Sun, Jan 4

Delta flights from Jamaica to Chicago Midway Airport

Our best Delta deals on Jamaica to Chicago Midway Airport flight tickets
Delta
Dec 24
MBJ8:00 amMontego Bay Sangster Intl
10h 26m
2 stops
MDW5:26 pmChicago Midway
Dec 30
MDW9:50 amChicago Midway
9h 51m
1 stop
MBJ8:41 pmMontego Bay Sangster Intl
$362
Find similar
Delta
Dec 21
MBJ8:00 amMontego Bay Sangster Intl
9h 20m
1 stop
MDW4:20 pmChicago Midway
Jan 4
MDW6:00 amChicago Midway
13h 41m
1 stop
MBJ8:41 pmMontego Bay Sangster Intl
$434
Find similar
Delta
Apr 9
MBJ11:35 amMontego Bay Sangster Intl
10h 54m
1 stop
MDW10:29 pmChicago Midway
Apr 16
MDW6:00 amChicago Midway
9h 29m
1 stop
MBJ3:29 pmMontego Bay Sangster Intl
$580
Find similar

Frontier flights from Jamaica to Chicago Midway Airport

Our best Frontier deals on Jamaica to Chicago Midway Airport flight tickets
Frontier
Dec 20
MBJ3:34 pmMontego Bay Sangster Intl
7h 38m
1 stop
MDW10:12 pmChicago Midway
Jan 3
MDW6:12 amChicago Midway
7h 17m
1 stop
MBJ2:29 pmMontego Bay Sangster Intl
$307
Find similar
Frontier
Dec 20
MBJ3:34 pmMontego Bay Sangster Intl
7h 38m
1 stop
MDW10:12 pmChicago Midway
Dec 25
MDW6:12 amChicago Midway
7h 17m
1 stop
MBJ2:29 pmMontego Bay Sangster Intl
$331
Find similar
Frontier
Dec 20
MBJ3:34 pmMontego Bay Sangster Intl
7h 38m
1 stop
MDW10:12 pmChicago Midway
Dec 27
MDW6:12 amChicago Midway
7h 17m
1 stop
MBJ2:29 pmMontego Bay Sangster Intl
$351
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Jamaica to Chicago Midway Airport 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 December 6, 2025.
Use the filters below to find and compare flights from Jamaica to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 12/20

3:34 pm-10:12 pm

1 stop7h 38m

Chicago Midway

Sat 1/3

6:12 am-2:29 pm

1 stop7h 17m

$307

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 12/20

3:34 pm-10:12 pm

1 stop7h 38m

Chicago Midway

Thu 12/25

6:12 am-2:29 pm

1 stop7h 17m

$331

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 12/20

3:34 pm-10:12 pm

1 stop7h 38m

Chicago Midway

Sat 12/27

6:12 am-2:29 pm

1 stop7h 17m

$351

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 12/24

3:49 pm-10:12 pm

1 stop7h 23m

Chicago Midway

Tue 12/30

6:14 am-2:29 pm

1 stop7h 15m

$357

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 12/24

8:00 am-5:26 pm

2 stops10h 26m

Chicago Midway

Tue 12/30

9:50 am-8:41 pm

1 stop9h 51m

$362

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 12/20

3:34 pm-9:04 pm

2 stops30h 30m

Chicago Midway

Thu 12/25

6:12 am-2:29 pm

1 stop7h 17m

$366

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 12/20

11:12 am-10:12 pm

1 stop12h 00m

Chicago Midway

Sat 1/3

7:05 am-2:54 pm

2 stops30h 49m

$405

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 12/20

11:12 am-10:12 pm

1 stop12h 00m

Chicago Midway

Sat 1/3

7:05 am-2:54 pm

2 stops30h 49m

$406

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 12/20

1:55 pm-5:05 pm

Nonstop4h 10m

Chicago Midway

Sat 1/3

5:30 am-1:50 pm

1 stop7h 20m

$421

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 12/21

8:00 am-4:20 pm

1 stop9h 20m

Chicago Midway

Sun 1/4

6:00 am-8:41 pm

1 stop13h 41m

$434

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 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, Saturday is the cheapest day to fly to Chicago Midway Airport from Jamaica. The lowest ticket price found for a Saturday departure recently was $532. 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, Monday 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 $689.

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 $549 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 is only 1 cabin class 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.

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

No. A direct flight is the cheapest option for a flight between Jamaica to Chicago Midway Airport.

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

Fastest flight time

4h 10m

Direct flights

Mon and Sun
The fastest flight from Jamaica to Chicago Midway Airport takes 4h 10m
Direct flights go from Jamaica to Chicago Midway Airport on Monday and Sunday. There are no airlines offering direct flights.
Search flight deals

  • 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
SouthwestPriceFrom $392Free CancellationRating
8.0
4,251 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
Chesterton
Monticello
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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