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Cheap flights from Jamaica to Chicago from $207

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 - 10:47 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
9h 15m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:46 pm - 2:27 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
19h 41m1 stop Atlanta Hartsfield-Jackson
$343Frontier
Sun, Aug 30 - Thu, Sep 10
Southwest Logo
2:15 pm - 10:25 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 10m2 stops Orlando Nashville Intl
Southwest Logo
7:55 pm - 11:55 amMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
16h 00m2 stops Baltimore/Washington Orlando
$453Southwest
Thu, Sep 24 - Mon, Sep 28
Southwest Logo
12:15 pm - 9:00 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 45m1 stop Baltimore/Washington
Southwest Logo
7:55 pm - 11:55 amMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
16h 00m2 stops Baltimore/Washington Orlando
$453Southwest
Thu, Sep 24 - Mon, Sep 28
Southwest Logo
2:15 pm - 10:45 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 30m1 stop Orlando
Southwest Logo
5:00 am - 1:15 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 15m1 stop Orlando
$454Southwest
Thu, Sep 24 - Mon, Sep 28
Frontier Logo
3:42 pm - 11:44 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 02m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 2:27 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 02m1 stop Atlanta Hartsfield-Jackson
$458Frontier
Mon, Sep 14 - Mon, Sep 21
Southwest Logo
12:55 pm - 9:25 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 30m1 stop Orlando
Southwest Logo
5:45 am - 11:50 amMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
6h 05m1 stop Orlando
$469Southwest
Tue, Sep 29 - Tue, Oct 6
Frontier Logo
1:32 pm - 10:47 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
9h 15m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:54 pm - 2:27 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
25h 33m2 stops Dallas/Fort Worth Atlanta Hartsfield-Jackson
$478Frontier
Sun, Aug 30 - Thu, Sep 10
Frontier Logo
1:32 pm - 10:47 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
9h 15m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:46 pm - 2:27 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
19h 41m1 stop Atlanta Hartsfield-Jackson
$503Frontier
Thu, Sep 3 - Thu, Sep 24
Southwest Logo
12:55 pm - 11:15 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
10h 20m2 stops Orlando Houston Hobby
Southwest Logo
5:45 am - 11:50 amMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
6h 05m1 stop Orlando
$529Southwest
Tue, Sep 29 - Tue, Oct 6
Frontier Logo
11:06 am - 6:26 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 20m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
2:04 pm - 1:08 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
22h 04m1 stop Atlanta Hartsfield-Jackson
$559Frontier
Fri, Nov 20 - Sun, Dec 13

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Frontier flights from Jamaica to Chicago Midway Airport

Our best Frontier deals on Jamaica to Chicago Midway Airport flight tickets
Frontier
Aug 30
MBJ1:32 pmMontego Bay Sangster Intl
9h 15m
1 stop
MDW10:47 pmChicago Midway
Sep 10
MDW6:46 pmChicago Midway
19h 41m
1 stop
MBJ2:27 pmMontego Bay Sangster Intl
$343
Frontier
Sep 14
MBJ3:42 pmMontego Bay Sangster Intl
8h 02m
1 stop
MDW11:44 pmChicago Midway
Sep 21
MDW6:25 amChicago Midway
8h 02m
1 stop
MBJ2:27 pmMontego Bay Sangster Intl
$458
Frontier
Aug 30
MBJ1:32 pmMontego Bay Sangster Intl
9h 15m
1 stop
MDW10:47 pmChicago Midway
Sep 10
MDW12:54 pmChicago Midway
25h 33m
2 stops
MBJ2:27 pmMontego Bay Sangster Intl
$478

Southwest flights from Jamaica to Chicago Midway Airport

Our best Southwest deals on Jamaica to Chicago Midway Airport flight tickets
Southwest
Sep 29
MBJ12:55 pmMontego Bay Sangster Intl
8h 30m
1 stop
MDW9:25 pmChicago Midway
Oct 6
MDW5:45 amChicago Midway
6h 05m
1 stop
MBJ11:50 amMontego Bay Sangster Intl
$469
Southwest
Sep 29
MBJ12:55 pmMontego Bay Sangster Intl
10h 20m
2 stops
MDW11:15 pmChicago Midway
Oct 6
MDW5:45 amChicago Midway
6h 05m
1 stop
MBJ11:50 amMontego Bay Sangster Intl
$529
Southwest
Dec 29
MBJ1:50 pmMontego Bay Sangster Intl
10h 20m
2 stops
MDW11:10 pmChicago Midway
Jan 3
MDW5:20 amChicago Midway
8h 25m
2 stops
MBJ2:45 pmMontego Bay Sangster Intl
$699

momondo Fare Finder

 
Use the filters below to find and compare flights from Jamaica to Chicago Midway Airport that are best for you.

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Route

Depart

Return

Price

Cheapest round-trip

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Sun 8/30

1:32 pm-10:47 pm

1 stop9h 15m

Chicago Midway

Thu 9/10

6:46 pm-2:27 pm

1 stop19h 41m

$343

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Thu 9/24

2:15 pm-10:25 pm

2 stops8h 10m

Chicago Midway

Mon 9/28

7:55 pm-11:55 am

2 stops16h 00m

$453

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Thu 9/24

12:15 pm-9:00 pm

1 stop8h 45m

Chicago Midway

Mon 9/28

7:55 pm-11:55 am

2 stops16h 00m

$453

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Thu 9/24

2:15 pm-10:45 pm

1 stop8h 30m

Chicago Midway

Mon 9/28

5:00 am-1:15 pm

1 stop8h 15m

$454

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Mon 9/14

3:42 pm-11:44 pm

1 stop8h 02m

Chicago Midway

Mon 9/21

6:25 am-2:27 pm

1 stop8h 02m

$458
Quickest round-trip

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Tue 9/29

12:55 pm-9:25 pm

1 stop8h 30m

Chicago Midway

Tue 10/6

5:45 am-11:50 am

1 stop6h 05m

$469

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Sun 8/30

1:32 pm-10:47 pm

1 stop9h 15m

Chicago Midway

Thu 9/10

12:54 pm-2:27 pm

2 stops25h 33m

$478

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Thu 9/3

1:32 pm-10:47 pm

1 stop9h 15m

Chicago Midway

Thu 9/24

6:46 pm-2:27 pm

1 stop19h 41m

$503

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Tue 9/29

12:55 pm-11:15 pm

2 stops10h 20m

Chicago Midway

Tue 10/6

5:45 am-11:50 am

1 stop6h 05m

$529

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Fri 11/20

11:06 am-6:26 pm

1 stop8h 20m

Chicago Midway

Sun 12/13

2:04 pm-1:08 pm

1 stop22h 04m

$559

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 24% 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

Best Price Found

$207

Fastest flight time

8h 02m

Direct flights

Sun
The best one-way flight to Chicago Midway Airport from Jamaica in the past 72 hours is $207. The best round-trip flight deal from Jamaica to Chicago Midway Airport found on momondo in the last 72 hours is $343.
The fastest flight from Jamaica to Chicago Midway Airport takes 8h 02m
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
8.0
4,219 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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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