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$167+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
1 adult, Economy
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Cheap flight deals from Jamaica to Chicago

Keep the following information in mind while searching for Jamaica to Chicago flight deals. Data was last updated septiembre 15, 2025.

Round-trip from

$239
(Cheapflightsfares)

One-way from

$167
(Cheapflightsfares)

Popular in

January

Cheapest in

September

Average price

$373

Good round-trip deal

$496 or less

Good one-way deal

$292 or less
From Jamaica to Chicago (CHI)
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One-way flight from Jamaica to Chicago (CHI)
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Highest demand for flights based on searches. 13% potential increase in price ($75 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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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Find 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 septiembre 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
mar. 10/712:09 pmMBJ - ORD
1 stop11h 36mSpirit Airlines
sáb. 10/117:43 pmORD - MBJ
1 stop15h 17mSpirit Airlines
Deal found 9/14$239
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
jue. 10/212:10 pmMBJ - ORD
1 stop10h 38mSpirit Airlines
dom. 10/55:05 amORD - MBJ
1 stop5h 55mSpirit Airlines
Deal found 9/14$249
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
jue. 10/912:14 pmKIN - ORD
1 stop11h 31mSpirit Airlines
jue. 1/85:59 pmORD - KIN
1 stop17h 14mSpirit Airlines
Deal found 9/14$329
This American Airlines deal was found by Cheapflights users on 9/14. 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.
mar. 10/71:50 pmMBJ - ORD
Nonstop4h 33mAmerican Airlines
sáb. 10/119:45 pmORD - MBJ
1 stop16h 30mAmerican Airlines
Deal found 9/14$338
This Mytrip deal was found by Cheapflights users on 9/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/212:08 pmKIN - ORD
1 stop10h 40mSpirit Airlines
dom. 10/55:05 amORD - KIN
1 stop6h 04mSpirit Airlines
Deal found 9/14$340
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/252:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
lun. 12/18:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
Deal found 9/15$340
This American Airlines deal was found by Cheapflights users on 9/15. 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.
mar. 11/252:14 pmMBJ - ORD
Nonstop4h 36mAmerican Airlines
lun. 12/17:11 amORD - MBJ
1 stop6h 39mAmerican Airlines
Deal found 9/15$344
This Mytrip deal was found by Cheapflights users on 9/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/1612:14 pmKIN - ORD
1 stop11h 31mSpirit Airlines
lun. 10/205:05 amORD - KIN
1 stop6h 04mSpirit Airlines
Deal found 9/13$345
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/255:59 pmMBJ - ORD
1 stop7h 03mDelta
lun. 12/19:46 amORD - MBJ
1 stop5h 48mDelta
Deal found 9/15$345
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
sáb. 9/2712:08 pmKIN - ORD
1 stop10h 40mSpirit Airlines
mar. 9/306:44 pmORD - KIN
1 stop16h 18mSpirit Airlines
Deal found 9/13$352
This Delta deal was found by Cheapflights users on 9/14. 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.
jue. 10/99:00 amKIN - ORD
1 stop7h 41mDelta
jue. 1/87:00 amORD - KIN
2 stops12h 00mDelta
Deal found 9/14$388
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/253:25 pmMBJ - MDW
2 stops9h 25mSouthwest
lun. 12/15:20 amMDW - MBJ
1 stop6h 30mSouthwest
Deal found 9/15$394

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 septiembre 15, 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

mar. 10/7

12:09 pm-11:45 pm

1 stop11h 36m

Chicago O'Hare Intl

sáb. 10/11

7:43 pm-11:00 am

1 stop15h 17m

$239

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

jue. 10/2

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

dom. 10/5

5:05 am-11:00 am

1 stop5h 55m

$249

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

jue. 10/9

12:14 pm-11:45 pm

1 stop11h 31m

Chicago O'Hare Intl

jue. 1/8

5:59 pm-12:13 pm

1 stop17h 14m

$329

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 11/25

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

lun. 12/1

8:42 am-1:46 pm

Nonstop4h 04m

$340

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

jue. 10/2

12:08 pm-10:48 pm

1 stop10h 40m

Chicago O'Hare Intl

dom. 10/5

5:05 am-11:09 am

1 stop6h 04m

$340

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 11/25

3:13 pm-6:54 pm

Nonstop4h 41m

Chicago O'Hare Intl

dom. 11/30

12:19 am-2:12 pm

1 stop12h 53m

$344

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 11/25

5:59 pm-12:02 am

1 stop7h 03m

Chicago O'Hare Intl

lun. 12/1

9:46 am-4:34 pm

1 stop5h 48m

$345

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

jue. 10/30

12:14 pm-1:03 am

1 stop12h 49m

Chicago O'Hare Intl

jue. 11/6

5:59 pm-12:13 pm

1 stop17h 14m

$345

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

jue. 10/16

12:14 pm-11:45 pm

1 stop11h 31m

Chicago O'Hare Intl

lun. 10/20

5:05 am-11:09 am

1 stop6h 04m

$345

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 10/7

12:10 pm-8:01 am

2 stops19h 51m

Chicago O'Hare Intl

sáb. 10/11

6:58 pm-11:00 am

2 stops16h 02m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 46 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, August is the cheapest month in which you can book a flight from Jamaica to Chicago (average of $245). Flying from Jamaica to Chicago in March is currently the most expensive (average of $321). 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 septiembre 15, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 4% on flights from Jamaica to Chicago by exploring options for tickets at noon.

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 septiembre 15, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, 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
8.0
Very good
7,954 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,929 reviews
Delta
8.0
Very good
7,954 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,954 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

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 9h 05m. There are 1709 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 $193. However, be on the lookout for offers from Southwest 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 Montego Bay Sangster Intl - Chicago O'Hare Intl, Kingston Norman Manley - Chicago O'Hare Intl and Montego Bay Sangster Intl - Chicago Midway.

  • What are the most reliable airlines from Jamaica to Chicago?

    The top 3 most reliable airlines when flying from Jamaica to Chicago are Qatar Airways (100%), American Airlines (85%) and British Airways (85%).

  • What are the cheapest flights from Jamaica to Chicago?

    Looking for the cheapest flight from Jamaica to Chicago? While on average our users pay $454, our data indicates the cheapest price to be $158. The most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl), is priced around $239.

  • 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, August is the cheapest month in which you can book a flight from Jamaica to Chicago (average of $245). Flying from Jamaica to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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.
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
Santo Domingo to O'Hare Intl flights
Punta Cana to O'Hare Intl flights
Luis Munoz Marin Intl to St. Louis flights
Santo Domingo to Midway flights
Santiago de los Caballeros to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Nassau to O'Hare Intl flights
Punta Cana to Midway flights
Kingston to O'Hare Intl flights
George Town to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Port of Spain to St. Louis flights
Aguadilla to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
Nassau to Midway flights
Saint Thomas Island to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Montego Bay to Midway flights
Simpson Bay to Midway flights
Oranjestad to St. Louis flights
St. John's to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Vieques to O'Hare Intl flights
St. George's to St. Louis flights
Nassau to St. Louis 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 5 airlines flying from Jamaica to Chicago

Discover the top 5 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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$369FlexibilityNo cancel feeOn-time65%
DeltaCheapest$322Average$588FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$348Average$525FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$392Average$550FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$409Average$484FlexibilityNo cancel feeOn-time69%

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