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Cheap flights from Jamaica to Chicago from $158

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 5/20. 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 Jamaica to Chicago

Recent round-trip flight deals from Jamaica to Chicago

Enter your travel dates to find the best prices.
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
$281Southwest
Wed, Jun 17 - Tue, Jun 23
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
$302Frontier
Wed, May 13 - Wed, May 27
Frontier Logo
1:16 pm - 11:04 am
MBJ
-
MDW
21h 48m
1 stop
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
$353Frontier
Fri, May 8 - Fri, May 15
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
$376Southwest
Thu, Jun 18 - Tue, Jun 23
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
Southwest Logo
6:00 am - 2:55 pm
MDW
-
MBJ
8h 55m
1 stop
$381Southwest
Wed, Jun 17 - Tue, Jun 23
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
$386Southwest
Thu, Jun 18 - Tue, Jun 23
Southwest Logo
11:45 am - 7:50 pm
MBJ
-
MDW
8h 05m
2 stops
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
$387Southwest
Wed, Jun 17 - Tue, Jun 23
Southwest Logo
2:20 pm - 12:40 am
MBJ
-
MDW
10h 20m
1 stop
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
$397Southwest
Thu, Jun 18 - Tue, Jun 23
Southwest Logo
2:20 pm - 12:15 am
MBJ
-
MDW
9h 55m
2 stops
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
$434Southwest
Thu, Jun 18 - Tue, Jun 23
Multiple Airlines Logo
1:17 pm - 10:14 pm
MBJ
-
MDW
8h 57m
1 stop
Multiple Airlines Logo
7:34 pm - 12:16 pm
MDW
-
MBJ
16h 42m
2 stops
$439Multiple Airlines
Sat, Apr 18 - Sat, Apr 25

Frontier flights from Jamaica to Chicago Midway Airport

Our best Frontier deals on Jamaica to Chicago Midway Airport flight tickets
Frontier
May 13
MBJ1:16 pmMontego Bay Sangster Intl
8h 46m
1 stop
MDW10:02 pmChicago Midway
May 27
MDW6:00 amChicago Midway
6h 11m
1 stop
MBJ12:11 pmMontego Bay Sangster Intl
$302
Frontier
May 8
MBJ1:16 pmMontego Bay Sangster Intl
21h 48m
1 stop
MDW11:04 amChicago Midway
May 15
MDW6:00 amChicago Midway
6h 11m
1 stop
MBJ12:11 pmMontego Bay Sangster Intl
$353

Delta flights from Jamaica to Chicago Midway Airport

Our best Delta deals on Jamaica to Chicago Midway Airport flight tickets
Delta
Apr 18
MBJ2:10 pmMontego Bay Sangster Intl
8h 18m
1 stop
MDW10:28 pmChicago Midway
Apr 25
MDW6:00 amChicago Midway
6h 54m
1 stop
MBJ12:54 pmMontego Bay Sangster Intl
$507
Delta
Mar 31
MBJ11:15 amMontego Bay Sangster Intl
11h 16m
1 stop
MDW10:31 pmChicago Midway
Jun 2
MDW6:23 amChicago Midway
9h 11m
1 stop
MBJ3:34 pmMontego Bay Sangster Intl
$867
Delta
Mar 31
MBJ1:38 pmMontego Bay Sangster Intl
8h 53m
1 stop
MDW10:31 pmChicago Midway
Jun 2
MDW6:23 amChicago Midway
9h 11m
1 stop
MBJ3:34 pmMontego Bay Sangster Intl
$882

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 March 24, 2026.
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

Cheapest round-trip
Quickest round-trip

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 6/17

1:50 pm-5:50 pm

Nonstop4h 00m

Chicago Midway

Tue 6/23

10:05 am-1:55 pm

Nonstop3h 50m

$281

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 5/13

1:16 pm-10:02 pm

1 stop8h 46m

Chicago Midway

Wed 5/27

6:00 am-12:11 pm

1 stop6h 11m

$302

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 5/8

1:16 pm-11:04 am

1 stop21h 48m

Chicago Midway

Fri 5/15

6:00 am-12:11 pm

1 stop6h 11m

$353

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 6/18

1:50 pm-5:50 pm

Nonstop4h 00m

Chicago Midway

Tue 6/23

10:05 am-1:55 pm

Nonstop3h 50m

$376

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 6/17

1:50 pm-5:50 pm

Nonstop4h 00m

Chicago Midway

Tue 6/23

6:00 am-2:55 pm

1 stop8h 55m

$381

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 6/18

1:50 pm-5:50 pm

Nonstop4h 00m

Chicago Midway

Tue 6/23

10:05 am-1:55 pm

Nonstop3h 50m

$386

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 6/17

11:45 am-7:50 pm

2 stops8h 05m

Chicago Midway

Tue 6/23

10:05 am-1:55 pm

Nonstop3h 50m

$387

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 6/18

2:20 pm-12:40 am

1 stop10h 20m

Chicago Midway

Tue 6/23

10:05 am-1:55 pm

Nonstop3h 50m

$397

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 6/18

2:20 pm-12:15 am

2 stops9h 55m

Chicago Midway

Tue 6/23

10:05 am-1:55 pm

Nonstop3h 50m

$434

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 4/18

1:17 pm-10:14 pm

1 stop8h 57m

Chicago Midway

Sat 4/25

7:34 pm-12:16 pm

2 stops16h 42m

$439

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 $463. 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 $532 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 00m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun
The fastest flight from Jamaica to Chicago Midway Airport takes 4h 00m
Direct flights go from Jamaica to Chicago Midway Airport on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is Southwest.
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
4,331 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
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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