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$153+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
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 December 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/15. 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 12/251:05 pmMBJ - ORD
1 stop6h 34mSpirit Airlines
Sun 1/258:43 pmORD - MBJ
1 stop14h 19mSpirit Airlines
Deal found 12/15$304
This FlightHub deal was found by Cheapflights users on 12/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/252:15 pmMBJ - ORD
2 stops22h 03mAir Canada
Sun 1/257:15 amORD - MBJ
1 stop9h 50mAir Canada
Deal found 12/15$383
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/253:51 pmMBJ - ORD
Nonstop4h 38mAmerican Airlines
Sun 1/2510:09 amORD - MBJ
Nonstop4h 13mAmerican Airlines
Deal found 12/15$390
This oojo deal was found by Cheapflights users on 12/15. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/271:19 pmKIN - ORD
1 stop12h 11mSpirit Airlines
Sat 1/35:00 amORD - KIN
1 stop6h 14mSpirit Airlines
Deal found 12/15$501
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Sat 12/2711:31 amKIN - ORD
2 stops10h 45mAmerican Airlines
Sat 1/34:41 pmORD - KIN
1 stop16h 31mAmerican Airlines
Deal found 12/16$658
This Priceline deal was found by Cheapflights users on 12/15. 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.
Thu 12/252:15 pmMBJ - ORD
2 stops18h 50mMultiple Airlines
Sun 1/257:45 amORD - MBJ
2 stops28h 18mMultiple Airlines
Deal found 12/15$871
This WestJet deal was found by Cheapflights users on 12/15. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:25 pmMBJ - MDW
2 stops15h 41mWestJet
Sun 1/259:32 amMDW - MBJ
2 stops27h 21mWestJet
Deal found 12/15$1,263

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 December 16, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$246
(Cheapflightsfares)

One-way from

$153
(Trip.com)

Popular in

February

Cheapest in

November

Average price

$441

Good round-trip deal

$414 or less

Good one-way deal

$237 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.
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From Jamaica to Chicago (CHI)
Search Deals
One-way flight from Jamaica to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Jamaica to Chicago (CHI).
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Price to beat on a one-way flight from Jamaica to Chicago (CHI).
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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 December 16, 2025.
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

Thu 1/15

12:57 pm-7:38 pm

1 stop7h 41m

Chicago O'Hare Intl

Thu 1/22

8:43 pm-12:02 pm

1 stop14h 19m

$246

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 12/25

1:05 pm-6:39 pm

1 stop6h 34m

Chicago O'Hare Intl

Sun 1/25

8:43 pm-12:02 pm

1 stop14h 19m

$304

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 1/15

12:57 pm-10:44 pm

2 stops10h 47m

Chicago O'Hare Intl

Thu 1/22

8:43 pm-12:02 pm

1 stop14h 19m

$321

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 1/14

4:45 pm-11:59 pm

1 stop8h 14m

Chicago O'Hare Intl

Wed 1/21

5:30 am-12:54 pm

1 stop6h 24m

$346

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 1/14

2:19 pm-10:07 pm

1 stop8h 48m

Chicago Midway

Wed 1/21

6:00 am-12:54 pm

1 stop5h 54m

$346

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 1/14

1:58 pm-10:34 pm

2 stops9h 36m

Chicago O'Hare Intl

Wed 1/21

6:54 am-3:16 pm

1 stop7h 22m

$359

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 1/15

3:12 pm-6:51 pm

Nonstop4h 39m

Chicago O'Hare Intl

Thu 1/22

10:09 am-3:22 pm

Nonstop4h 13m

$362

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 12/25

2:15 pm-11:18 am

2 stops22h 03m

Chicago O'Hare Intl

Sun 1/25

7:15 am-6:05 pm

1 stop9h 50m

$383

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 12/25

3:51 pm-7:29 pm

Nonstop4h 38m

Chicago O'Hare Intl

Sun 1/25

10:09 am-3:22 pm

Nonstop4h 13m

$390

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 1/30

9:00 am-6:45 pm

2 stops10h 45m

Chicago O'Hare Intl

Fri 2/6

7:05 am-8:00 pm

1 stop11h 55m

$400

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 45 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 $477). 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 December 16, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 41% on flights from Jamaica to Chicago by exploring options for tickets in the morning.

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 December 16, 2025.
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
8,008 reviews

Food

7.3

Overall

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

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
8,008 reviews
Delta
7.9
Good
8,008 reviews

Food

7.3

Overall

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

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
11,049 reviews
Delta
7.9
Good
8,008 reviews

Food

7.3

Overall

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

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 7h 41m. 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 United 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 Midway and Montego Bay Sangster Intl - Chicago O'Hare Intl.

  • What are the cheapest flights from Jamaica to Chicago?

    Looking for the cheapest flight from Jamaica to Chicago? While on average our users pay $345, our data indicates the cheapest price to be $212. The most popular route (Kingston Norman Manley - Chicago O'Hare Intl), is priced around $349.

  • 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 $477). 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.
Punta Cana to O'Hare Intl flights
Punta Cana to Midway flights
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Oranjestad to O'Hare Intl flights
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Saint Thomas Island to O'Hare Intl flights
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Christiansted to O'Hare Intl flights
Santo Domingo to Midway flights
Nassau to St. Louis flights
Nassau to Midway flights
Kingston to O'Hare Intl flights
George Town to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
Aguadilla to O'Hare Intl flights
Montego Bay to Midway flights
Montego Bay to O'Hare Intl flights
Port of Spain to St. Louis flights
Oranjestad to St. Louis flights
Saint Thomas Island to St. Louis flights
Road Town to O'Hare Intl flights
Simpson Bay to Midway flights
Port Au Prince to O'Hare Intl flights
Roseau to O'Hare Intl flights
Culebra to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
St. John's to O'Hare Intl flights
Vieques to O'Hare Intl flights
Port Au Prince to Midway flights
St. George's to St. Louis 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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$256Average$371FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$348Average$510FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$349Average$480FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$392Average$536FlexibilityNo cancel feeOn-time63%

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