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Cheap flights from Jamaica to Chicago from $194

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 7/4. 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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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
1:32 pm - 10:08 pm
MBJ
-
MDW
8h 36m
1 stop
Frontier Logo
6:00 am - 12:27 pm
MDW
-
MBJ
6h 27m
1 stop
$369Frontier
Fri, Aug 14 - Mon, Aug 17
Frontier Logo
1:26 pm - 10:11 pm
MBJ
-
MDW
8h 45m
1 stop
Frontier Logo
6:00 am - 12:21 pm
MDW
-
MBJ
6h 21m
1 stop
$375Frontier
Fri, Jun 19 - Fri, Jun 26
Frontier Logo
1:32 pm - 11:07 am
MBJ
-
MDW
21h 35m
1 stop
Frontier Logo
6:00 am - 12:27 pm
MDW
-
MBJ
6h 27m
1 stop
$388Frontier
Fri, Aug 14 - Mon, Aug 17
Frontier Logo
1:32 pm - 10:08 pm
MBJ
-
MDW
8h 36m
1 stop
Frontier Logo
6:00 am - 12:21 pm
MDW
-
MBJ
6h 21m
1 stop
$389Frontier
Fri, Aug 7 - Mon, Aug 31
Frontier Logo
1:32 pm - 10:08 pm
MBJ
-
MDW
8h 36m
1 stop
Frontier Logo
12:11 pm - 12:27 pm
MDW
-
MBJ
24h 16m
1 stop
$394Frontier
Fri, Jul 17 - Sat, Jul 25
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
$395Frontier
Fri, May 29 - Mon, Jun 1
Southwest Logo
11:35 am - 3:45 pm
MBJ
-
MDW
4h 10mnonstop
Southwest Logo
9:55 am - 1:45 pm
MDW
-
MBJ
3h 50mnonstop
$409Southwest
Sat, May 23 - Sat, May 30
Southwest Logo
11:35 am - 3:45 pm
MBJ
-
MDW
4h 10mnonstop
Southwest Logo
6:10 am - 1:30 pm
MDW
-
MBJ
7h 20m
1 stop
$436Southwest
Sat, May 23 - Sat, May 30
Southwest Logo
11:45 am - 8:10 pm
MBJ
-
MDW
8h 25m
1 stop
Southwest Logo
7:15 am - 1:15 pm
MDW
-
MBJ
6h 00m
1 stop
$446Southwest
Mon, Jul 20 - Thu, Aug 20
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
Frontier Logo
12:27 pm - 12:21 pm
MDW
-
MBJ
23h 54m
1 stop
$461Frontier
Thu, Jun 4 - Thu, Jun 11

Frontier flights from Jamaica to Chicago Midway Airport

Our best Frontier deals on Jamaica to Chicago Midway Airport flight tickets
Frontier
Aug 14
MBJ1:32 pmMontego Bay Sangster Intl
8h 36m
1 stop
MDW10:08 pmChicago Midway
Aug 17
MDW6:00 amChicago Midway
6h 27m
1 stop
MBJ12:27 pmMontego Bay Sangster Intl
$369
Frontier
Jun 19
MBJ1:26 pmMontego Bay Sangster Intl
8h 45m
1 stop
MDW10:11 pmChicago Midway
Jun 26
MDW6:00 amChicago Midway
6h 21m
1 stop
MBJ12:21 pmMontego Bay Sangster Intl
$375
Frontier
Aug 14
MBJ1:32 pmMontego Bay Sangster Intl
21h 35m
1 stop
MDW11:07 amChicago Midway
Aug 17
MDW6:00 amChicago Midway
6h 27m
1 stop
MBJ12:27 pmMontego Bay Sangster Intl
$388

Southwest flights from Jamaica to Chicago Midway Airport

Our best Southwest deals on Jamaica to Chicago Midway Airport flight tickets
Southwest
May 23
MBJ11:35 amMontego Bay Sangster Intl
4h 10m
MDW3:45 pmChicago Midway
May 30
MDW9:55 amChicago Midway
3h 50m
MBJ1:45 pmMontego Bay Sangster Intl
$409
Southwest
May 23
MBJ11:35 amMontego Bay Sangster Intl
4h 10m
MDW3:45 pmChicago Midway
May 30
MDW6:10 amChicago Midway
7h 20m
1 stop
MBJ1:30 pmMontego Bay Sangster Intl
$436
Southwest
Jul 20
MBJ11:45 amMontego Bay Sangster Intl
8h 25m
1 stop
MDW8:10 pmChicago Midway
Aug 20
MDW7:15 amChicago Midway
6h 00m
1 stop
MBJ1:15 pmMontego Bay Sangster Intl
$446

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 May 9, 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

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 8/14

1:32 pm-10:08 pm

1 stop8h 36m

Chicago Midway

Mon 8/17

6:00 am-12:27 pm

1 stop6h 27m

$369

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 6/19

1:26 pm-10:11 pm

1 stop8h 45m

Chicago Midway

Fri 6/26

6:00 am-12:21 pm

1 stop6h 21m

$375

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 8/14

1:32 pm-11:07 am

1 stop21h 35m

Chicago Midway

Mon 8/17

6:00 am-12:27 pm

1 stop6h 27m

$388

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 8/7

1:32 pm-10:08 pm

1 stop8h 36m

Chicago Midway

Mon 8/31

6:00 am-12:21 pm

1 stop6h 21m

$389

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 7/17

1:32 pm-10:08 pm

1 stop8h 36m

Chicago Midway

Sat 7/25

12:11 pm-12:27 pm

1 stop24h 16m

$394

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 5/29

1:16 pm-10:02 pm

1 stop8h 46m

Chicago Midway

Mon 6/1

6:00 am-12:11 pm

1 stop6h 11m

$395
Quickest round-trip

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 5/23

11:35 am-3:45 pm

Nonstop4h 10m

Chicago Midway

Sat 5/30

9:55 am-1:45 pm

Nonstop3h 50m

$409

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 5/23

11:35 am-3:45 pm

Nonstop4h 10m

Chicago Midway

Sat 5/30

6:10 am-1:30 pm

1 stop7h 20m

$436

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Mon 7/20

11:45 am-8:10 pm

1 stop8h 25m

Chicago Midway

Thu 8/20

7:15 am-1:15 pm

1 stop6h 00m

$446

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 6/4

1:16 pm-10:02 pm

1 stop8h 46m

Chicago Midway

Thu 6/11

12:27 pm-12:21 pm

1 stop23h 54m

$461

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 $543 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

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

6h 47m

Direct flights

Sun
The fastest flight from Jamaica to Chicago Midway Airport takes 6h 47m
Direct flights go from Jamaica to Chicago Midway Airport on Sunday. The only airline offering direct flights is Southwest.
Search flight deals

Frequently asked questions about flying from Jamaica to Chicago Midway Airport

  • 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 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?

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
Munster
Schererville
Crown Point
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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