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$149+ Cheap flights from Jamaica to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheap flight deals from Jamaica to Chicago

Cheapest flights from Jamaica to Chicago
Explore the most affordable flight options available from Jamaica to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 28, 2026.

This Priceline deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/251:00 pm
MBJ
-
ORD
1 stop7h 11m
Spirit Airlines
Wed 3/45:15 am
ORD
-
MBJ
1 stop5h 47m
Spirit Airlines
Deal found 1/27$222
This Cheapflightsfares deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2412:00 pm
MBJ
-
ORD
1 stop7h 46m
Spirit Airlines
Tue 4/148:41 pm
ORD
-
MBJ
1 stop14h 21m
Spirit Airlines
Deal found 1/27$269
This Cheapflightsfares deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2912:57 pm
MBJ
-
ORD
1 stop11h 49m
Spirit Airlines
Sat 2/145:15 am
ORD
-
MBJ
1 stop5h 47m
Spirit Airlines
Deal found 1/26$299
This American Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/241:14 pm
MBJ
-
ORD
Nonstop4h 41m
American Airlines
Tue 4/148:10 am
ORD
-
MBJ
Nonstop4h 05m
American Airlines
Deal found 1/27$320
This United Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/241:48 pm
MBJ
-
ORD
Nonstop4h 25m
United Airlines
Tue 4/148:45 am
ORD
-
MBJ
1 stop6h 25m
United Airlines
Deal found 1/27$325
This American Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/143:20 pm
MBJ
-
ORD
1 stop8h 33m
American Airlines
Mon 5/186:58 pm
ORD
-
MBJ
1 stop16h 53m
American Airlines
Deal found 1/27$335
This American Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/131:15 pm
MBJ
-
ORD
Nonstop4h 43m
American Airlines
Tue 4/218:10 am
ORD
-
MBJ
Nonstop4h 05m
American Airlines
Deal found 1/27$345
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/144:55 pm
MBJ
-
ORD
2 stops14h 31m
Delta
Sun 5/179:30 am
ORD
-
MBJ
1 stop5h 59m
Delta
Deal found 1/26$351
This Delta deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/142:40 pm
MBJ
-
MDW
1 stop7h 05m
Delta
Mon 5/186:00 am
MDW
-
MBJ
1 stop7h 16m
Delta
Deal found 1/27$351
This United Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:12 pm
MBJ
-
ORD
1 stop7h 31m
United Airlines
Tue 4/218:45 am
ORD
-
MBJ
1 stop6h 25m
United Airlines
Deal found 1/27$365
This Cheapflightsfares deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1412:00 pm
KIN
-
ORD
1 stop7h 48m
Spirit Airlines
Mon 5/185:32 pm
ORD
-
KIN
1 stop17h 33m
Spirit Airlines
Deal found 1/28$367
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1912:00 pm
KIN
-
ORD
1 stop9h 17m
Multiple Airlines
Mon 8/315:32 pm
ORD
-
KIN
1 stop17h 33m
Multiple Airlines
Deal found 1/27$371

Find flight deals from Jamaica to Chicago

Keep the following information in mind while searching for Jamaica to Chicago flight deals. Data was last updated January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$222
(Priceline)

One-way from

$149
(Super.com)

Popular in

June

Cheapest in

November

Average price

$449

Good round-trip deal

$365 or less

Good one-way deal

$282 or less
Provider with most accurate pricing for Montego Bay Sangster Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-Chicago (CHI) flights.
Search Deals
From Jamaica to Chicago (CHI)
Search Deals
One-way flight from Jamaica to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($73 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Jamaica to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Jamaica to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jamaica to Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated January 28, 2026.
Use the filters below to find and compare flights from Jamaica to Chicago that are best for you.

Fly from

Jamaica

Fly to

Chicago

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 2/25

1:00 pm-7:11 pm

1 stop7h 11m

Chicago O'Hare Intl

Wed 3/4

5:15 am-12:02 pm

1 stop5h 47m

$222

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 3/24

1:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Tue 4/14

8:45 am-3:10 pm

1 stop6h 25m

$325

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/14

3:20 pm-11:53 pm

1 stop8h 33m

Chicago O'Hare Intl

Mon 5/18

6:58 pm-11:51 am

1 stop16h 53m

$335

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/14

1:15 pm-5:58 pm

Nonstop4h 43m

Chicago O'Hare Intl

Sun 5/17

8:10 am-12:15 pm

Nonstop4h 05m

$345

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 4/13

1:15 pm-5:58 pm

Nonstop4h 43m

Chicago O'Hare Intl

Tue 4/21

5:00 am-11:24 am

1 stop6h 24m

$350

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/14

2:40 pm-11:55 pm

1 stop9h 15m

Chicago O'Hare Intl

Sun 5/17

7:10 am-1:16 pm

1 stop6h 06m

$351

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/14

4:55 pm-7:26 am

2 stops14h 31m

Chicago O'Hare Intl

Mon 5/18

7:10 am-1:16 pm

1 stop6h 06m

$351

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 3/24

11:15 am-11:54 pm

1 stop12h 39m

Chicago O'Hare Intl

Tue 4/14

7:00 am-3:17 pm

2 stops8h 17m

$351

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 5/14

2:40 pm-9:45 pm

1 stop7h 05m

Chicago Midway

Mon 5/18

6:00 am-1:16 pm

1 stop7h 16m

$351

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 5/14

12:00 pm-7:48 pm

1 stop7h 48m

Chicago O'Hare Intl

Mon 5/18

5:32 pm-11:05 am

1 stop17h 33m

$367

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 37 results
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Best time to book a flight from Jamaica to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Jamaica with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Jamaica to Chicago

What is the cheapest month to book a flight from Jamaica to Chicago?

Currently, October is the cheapest month in which you can book a flight from Jamaica to Chicago (average of $289). Flying from Jamaica to Chicago in March is currently the most expensive (average of $455). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from JM to CHI?

Find hourly flight availability from Jamaica to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 28, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Jamaica to Chicago as you normally would.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated January 28, 2026.
Peruse reviews from past customers who have flown with Delta and American Airlines from Jamaica to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,123 reviews

Boarding

8.1

Food

7.2

Entertainment

7.8

Comfort

7.9

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,123 reviews
Delta
7.9
Good
8,123 reviews

Boarding

8.1

Food

7.2

Entertainment

7.8

Comfort

7.9

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,201 reviews
Delta
7.9
Good
8,123 reviews

Boarding

8.1

Food

7.2

Entertainment

7.8

Comfort

7.9

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Jamaica to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Jamaica to Chicago?

    Departing from Jamaica to Chicago will take you 4h 25m. There are 1724 mi between Jamaica and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Jamaica to Chicago one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $182. However, be on the lookout for offers from Frontier and American Airlines, as they are both options that can get you from Jamaica to Chicago for a low price.

  • What are the most popular routes from Jamaica to Chicago?

    The most popular flight routes from Jamaica to Chicago are Kingston Norman Manley - Chicago O'Hare Intl, Montego Bay Sangster Intl - Chicago O'Hare Intl and Montego Bay Sangster Intl - Chicago Midway.

  • What are the cheapest flights from Jamaica to Chicago?

    Looking for the cheapest flight from Jamaica to Chicago? While on average our users pay $396, our data indicates the cheapest price to be $236. The most popular route (Kingston Norman Manley - Chicago O'Hare Intl), is priced around $371.

  • Can I find deals for flights from Jamaica to Chicago that include hotel bookings?

    Yes. In addition to deals on Jamaica to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Jamaica to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Jamaica to Chicago.

  • Can I find deals for business class flights from Jamaica to Chicago?

    Yes. Cheapflights offers flight deals from Jamaica to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Jamaica to Chicago?

    Currently, October is the cheapest month in which you can book a flight from Jamaica to Chicago (average of $289). Flying from Jamaica to Chicago in March is currently the most expensive (average of $455). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Jamaica to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Port of Spain to O'Hare Intl flights
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Port of Spain to St. Louis flights
Nassau to St. Louis flights
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St. George's to St. Louis flights
Vieques to O'Hare Intl flights
Saint Thomas Island to St. Louis flights
Port Au Prince to O'Hare Intl flights
Road Town to O'Hare Intl flights
Roseau to O'Hare Intl flights
Culebra to O'Hare Intl flights
Port Au Prince to Midway flights
Aguadilla to Midway flights

Top 4 airlines flying from Jamaica to Chicago

Discover the top 4 airlines that operate flights from Jamaica to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$256Average$371FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$348Average$495FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$349Average$480FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$392Average$536FlexibilityNo cancel feeOn-time63%

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