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Cheap flights from Jamaica to Chicago from $193

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 9/25. 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

Frontier Logo
2:05 pm - 11:17 pmMBJ-MDW
9h 12m1 stop
Frontier Logo
6:15 am - 12:45 pmMDW-MBJ
6h 30m1 stop
$327Frontier
Find Deal
Sat, Sep 13 - Sat, Oct 4
Frontier Logo
2:05 pm - 11:17 pmMBJ-MDW
9h 12m1 stop
Frontier Logo
6:20 am - 12:45 pmMDW-MBJ
6h 25m1 stop
$329Frontier
Find Deal
Sat, Sep 20 - Mon, Sep 22
Frontier Logo
2:12 pm - 11:20 pmMBJ-MDW
9h 08m1 stop
Frontier Logo
5:15 pm - 12:45 pmMDW-MBJ
19h 30m1 stop
$334Frontier
Find Deal
Thu, Sep 18 - Fri, Sep 19
Frontier Logo
2:12 pm - 11:20 pmMBJ-MDW
9h 08m1 stop
Frontier Logo
6:20 am - 12:41 pmMDW-MBJ
6h 21m1 stop
$339Frontier
Find Deal
Fri, Sep 19 - Sun, Sep 21
Delta Logo
12:50 pm - 9:47 amMBJ-MDW
20h 57m2 stops
Delta Logo
1:43 pm - 11:25 amMDW-MBJ
21h 42m2 stops
$344Delta
Find Deal
Fri, Sep 19 - Mon, Sep 22
Delta Logo
2:35 pm - 8:40 amMBJ-MDW
18h 05m2 stops
Delta Logo
6:00 am - 12:07 pmMDW-MBJ
6h 07m1 stop
$345Delta
Find Deal
Thu, Oct 2 - Tue, Oct 7
Logo
2:05 pm - 11:17 pmMBJ-MDW
9h 12m1 stop
Logo
5:15 pm - 11:05 amMDW-MBJ
17h 50m2 stops
$375
Find Deal
Sat, Sep 20 - Mon, Sep 22
Logo
12:10 pm - 7:11 amMBJ-MDW
19h 01m2 stops
Logo
5:15 pm - 12:45 pmMDW-MBJ
19h 30m1 stop
$428
Find Deal
Sun, Sep 14 - Fri, Sep 19
Southwest Logo
12:55 pm - 10:25 pmMBJ-MDW
9h 30m2 stops
Southwest Logo
6:15 am - 12:25 pmMDW-MBJ
6h 10m1 stop
$433Southwest
Find Deal
Wed, Sep 17 - Sat, Sep 20
Southwest Logo
12:50 pm - 8:40 pmMBJ-MDW
7h 50m2 stops
Southwest Logo
5:45 am - 1:25 pmMDW-MBJ
7h 40m2 stops
$488Southwest
Find Deal
Fri, Oct 3 - Tue, Oct 7

Delta flights from Jamaica to Chicago Midway Airport

Our best Delta deals on Jamaica to Chicago Midway Airport flight tickets
Delta
Sep 19
MBJ12:50 pmMontego Bay Sangster Intl
20h 57m
2 stops
MDW9:47 amChicago Midway
Sep 22
MDW1:43 pmChicago Midway
21h 42m
2 stops
MBJ11:25 amMontego Bay Sangster Intl
$344
Find similar
Delta
Oct 2
MBJ2:35 pmMontego Bay Sangster Intl
18h 05m
2 stops
MDW8:40 amChicago Midway
Oct 7
MDW6:00 amChicago Midway
6h 07m
1 stop
MBJ12:07 pmMontego Bay Sangster Intl
$345
Find similar
Delta
Oct 4
MBJ12:50 pmMontego Bay Sangster Intl
22h 58m
2 stops
MDW11:48 amChicago Midway
Oct 7
MDW6:00 amChicago Midway
6h 07m
1 stop
MBJ12:07 pmMontego Bay Sangster Intl
$370
Find similar

Southwest flights from Jamaica to Chicago Midway Airport

Our best Southwest deals on Jamaica to Chicago Midway Airport flight tickets
Southwest
Sep 17
MBJ12:55 pmMontego Bay Sangster Intl
9h 30m
2 stops
MDW10:25 pmChicago Midway
Sep 20
MDW6:15 amChicago Midway
6h 10m
1 stop
MBJ12:25 pmMontego Bay Sangster Intl
$433
Find similar
Southwest
Oct 3
MBJ12:50 pmMontego Bay Sangster Intl
7h 50m
2 stops
MDW8:40 pmChicago Midway
Oct 7
MDW5:45 amChicago Midway
7h 40m
2 stops
MBJ1:25 pmMontego Bay Sangster Intl
$488
Find similar
Southwest
Sep 3
MBJ12:55 pmMontego Bay Sangster Intl
8h 45m
1 stop
MDW9:40 pmChicago Midway
Sep 5
MDW6:35 amChicago Midway
7h 25m
1 stop
MBJ2:00 pmMontego Bay Sangster Intl
$566
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 August 28, 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 9/13

2:05 pm-11:17 pm

1 stop9h 12m

Chicago Midway

Sat 10/4

6:15 am-12:45 pm

1 stop6h 30m

$327

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 9/20

2:05 pm-11:17 pm

1 stop9h 12m

Chicago Midway

Mon 9/22

6:20 am-12:45 pm

1 stop6h 25m

$329

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 9/18

2:12 pm-11:20 pm

1 stop9h 08m

Chicago Midway

Fri 9/19

5:15 pm-12:45 pm

1 stop19h 30m

$334

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 9/19

2:12 pm-11:20 pm

1 stop9h 08m

Chicago Midway

Sun 9/21

6:20 am-12:41 pm

1 stop6h 21m

$339

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 9/19

12:50 pm-9:47 am

2 stops20h 57m

Chicago Midway

Mon 9/22

1:43 pm-11:25 am

2 stops21h 42m

$344

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 10/2

2:35 pm-8:40 am

2 stops18h 05m

Chicago Midway

Tue 10/7

6:00 am-12:07 pm

1 stop6h 07m

$345

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 9/20

2:05 pm-11:17 pm

1 stop9h 12m

Chicago Midway

Mon 9/22

5:15 pm-11:05 am

2 stops17h 50m

$375

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 9/14

12:10 pm-7:11 am

2 stops19h 01m

Chicago Midway

Fri 9/19

5:15 pm-12:45 pm

1 stop19h 30m

$428

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 9/17

12:55 pm-10:25 pm

2 stops9h 30m

Chicago Midway

Sat 9/20

6:15 am-12:25 pm

1 stop6h 10m

$433

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 10/3

12:50 pm-8:40 pm

2 stops7h 50m

Chicago Midway

Tue 10/7

5:45 am-1:25 pm

2 stops7h 40m

$488

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, 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 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?

You could potentially save up to 10% on your flight if you consider stops on a Jamaica to Chicago Midway Airport flight.

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

Sun
The fastest flight from Jamaica to Chicago Midway Airport takes 4h 10m
Direct flights go from Jamaica to Chicago Midway Airport on 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
4,242 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
Lansing
Portage
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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