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Cheap flights from Jamaica to Chicago from $210

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 9/17. 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
1 adult, Economy, 0 bags

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 - 11:07 am
MBJ
-
MDW
21h 35m
1 stop
Frontier Logo
11:45 am - 12:17 pm
MDW
-
MBJ
24h 32m
1 stop
$484Frontier
Sat, Aug 1 - Sat, Aug 29
Delta Logo
2:26 pm - 10:36 pm
MBJ
-
MDW
8h 10m
1 stop
Delta Logo
6:05 am - 3:34 pm
MDW
-
MBJ
9h 29m
1 stop
$487Delta
Sat, Aug 22 - Mon, Aug 24
Southwest Logo
2:15 pm - 9:30 pm
MBJ
-
MDW
7h 15m
1 stop
Southwest Logo
7:10 am - 2:25 pm
MDW
-
MBJ
7h 15m
1 stop
$489Southwest
Fri, Sep 4 - Sun, Sep 13
Southwest Logo
2:15 pm - 10:20 pm
MBJ
-
MDW
8h 05m
2 stops
Southwest Logo
5:10 am - 11:45 am
MDW
-
MBJ
6h 35m
1 stop
$494Southwest
Fri, Sep 4 - Sun, Sep 13
Frontier Logo
1:32 pm - 10:03 pm
MBJ
-
MDW
8h 31m
1 stop
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
$505Frontier
Thu, Jul 16 - Tue, Jul 21
Frontier Logo
1:32 pm - 10:03 pm
MBJ
-
MDW
8h 31m
1 stop
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
$506Frontier
Mon, Aug 3 - Mon, Aug 10
Southwest Logo
1:50 pm - 8:55 pm
MBJ
-
MDW
7h 05m
1 stop
Southwest Logo
7:55 pm - 11:55 am
MDW
-
MBJ
16h 00m
2 stops
$519Southwest
Sat, Aug 22 - Mon, Aug 24
Southwest Logo
2:55 pm - 10:00 pm
MBJ
-
MDW
7h 05m
1 stop
Southwest Logo
5:55 am - 1:15 pm
MDW
-
MBJ
7h 20m
2 stops
$522Southwest
Mon, Aug 3 - Mon, Aug 10
Southwest Logo
12:20 pm - 10:00 pm
MBJ
-
MDW
9h 40m
2 stops
Southwest Logo
7:50 pm - 12:55 pm
MDW
-
MBJ
17h 05m
2 stops
$542Southwest
Sat, Aug 22 - Mon, Aug 24
Southwest Logo
2:30 pm - 6:35 pm
MBJ
-
MDW
4h 05mnonstop
Southwest Logo
7:25 am - 1:15 pm
MDW
-
MBJ
5h 50m
1 stop
$549Southwest
Sat, Jul 4 - Mon, Aug 31

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Southwest flights from Jamaica to Chicago Midway Airport

Our best Southwest deals on Jamaica to Chicago Midway Airport flight tickets
Southwest
Sep 4
MBJ2:15 pmMontego Bay Sangster Intl
7h 15m
1 stop
MDW9:30 pmChicago Midway
Sep 13
MDW7:10 amChicago Midway
7h 15m
1 stop
MBJ2:25 pmMontego Bay Sangster Intl
$489
Southwest
Sep 4
MBJ2:15 pmMontego Bay Sangster Intl
8h 05m
2 stops
MDW10:20 pmChicago Midway
Sep 13
MDW5:10 amChicago Midway
6h 35m
1 stop
MBJ11:45 amMontego Bay Sangster Intl
$494
Southwest
Aug 22
MBJ1:50 pmMontego Bay Sangster Intl
7h 05m
1 stop
MDW8:55 pmChicago Midway
Aug 24
MDW7:55 pmChicago Midway
16h 00m
2 stops
MBJ11:55 amMontego Bay Sangster Intl
$519

WestJet flights from Jamaica to Chicago Midway Airport

Our best WestJet deals on Jamaica to Chicago Midway Airport flight tickets
WestJet
Aug 1
MBJ7:30 pmMontego Bay Sangster Intl
22h 55m
2 stops
MDW6:25 pmChicago Midway
Aug 29
MDW6:42 pmChicago Midway
41h 03m
2 stops
MBJ11:45 amMontego Bay Sangster Intl
$1,063
WestJet
Aug 1
MBJ7:30 pmMontego Bay Sangster Intl
22h 55m
2 stops
MDW6:25 pmChicago Midway
Aug 29
MDW6:42 pmChicago Midway
23h 48m
3 stops
MBJ6:30 pmMontego Bay Sangster Intl
$1,254
WestJet
Jun 25
MBJ12:45 pmMontego Bay Sangster Intl
20h 29m
3 stops
MDW9:14 amChicago Midway
Jul 4
MDW1:26 pmChicago Midway
20h 04m
2 stops
MBJ9:30 amMontego Bay Sangster Intl
$1,451

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 June 23, 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

Sat 8/1

1:32 pm-11:07 am

1 stop21h 35m

Chicago Midway

Sat 8/29

11:45 am-12:17 pm

1 stop24h 32m

$484

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 8/22

2:26 pm-10:36 pm

1 stop8h 10m

Chicago Midway

Mon 8/24

6:05 am-3:34 pm

1 stop9h 29m

$487

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 9/4

2:15 pm-9:30 pm

1 stop7h 15m

Chicago Midway

Sun 9/13

7:10 am-2:25 pm

1 stop7h 15m

$489

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 9/4

2:15 pm-10:20 pm

2 stops8h 05m

Chicago Midway

Sun 9/13

5:10 am-11:45 am

1 stop6h 35m

$494

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 7/16

1:32 pm-10:03 pm

1 stop8h 31m

Chicago Midway

Tue 7/21

6:05 am-12:27 pm

1 stop6h 22m

$505

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Mon 8/3

1:32 pm-10:03 pm

1 stop8h 31m

Chicago Midway

Mon 8/10

6:05 am-12:27 pm

1 stop6h 22m

$506

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 8/22

1:50 pm-8:55 pm

1 stop7h 05m

Chicago Midway

Mon 8/24

7:55 pm-11:55 am

2 stops16h 00m

$519

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Mon 8/3

2:55 pm-10:00 pm

1 stop7h 05m

Chicago Midway

Mon 8/10

5:55 am-1:15 pm

2 stops7h 20m

$522

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 8/22

12:20 pm-10:00 pm

2 stops9h 40m

Chicago Midway

Mon 8/24

7:50 pm-12:55 pm

2 stops17h 05m

$542
Quickest round-trip

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 7/4

2:30 pm-6:35 pm

Nonstop4h 05m

Chicago Midway

Mon 8/31

7:25 am-1:15 pm

1 stop5h 50m

$549

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 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 $473 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 Airport flights?

There is only 1 cabin class available to choose from on Jamaica to Chicago Midway Airport 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 2% 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

7h 15m

Direct flights

Sun
The fastest flight from Jamaica to Chicago Midway Airport takes 7h 15m
Direct flights go from Jamaica to Chicago Midway Airport on Sunday. There are no airlines offering direct flights.
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 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 $281Free CancellationRating
7.9
4,243 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
Portage
Saint Joseph
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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