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$171+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
nov. 29 — déc. 61
sam. 11/29
sam. 12/6
1 adult, Economy
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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 octobre 30, 2025.

This Priceline deal was found by Cheapflights users on 10/30. 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.
jeu. 11/131:07 pmMBJ - ORD
1 stop8h 20mSpirit Airlines
dim. 11/165:10 amORD - MBJ
1 stop5h 52mSpirit Airlines
Deal found 10/30$287
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 12/122:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
ven. 1/28:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
Deal found 10/28$320
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 11/232:14 pmMBJ - ORD
Nonstop4h 36mAmerican Airlines
dim. 11/3011:59 pmORD - MBJ
1 stop14h 00mAmerican Airlines
Deal found 10/28$330
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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.
dim. 11/231:07 pmMBJ - ORD
1 stop11h 06mSpirit Airlines
dim. 11/305:00 amORD - MBJ
1 stop6h 02mSpirit Airlines
Deal found 10/28$337
This American Airlines deal was found by Cheapflights users on 10/29. 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.
mer. 11/262:14 pmMBJ - ORD
Nonstop4h 36mAmerican Airlines
mer. 12/310:15 amORD - MBJ
Nonstop4h 07mAmerican Airlines
Deal found 10/29$351
This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/252:24 pmKIN - ORD
1 stop9h 49mSpirit Airlines
mar. 12/25:00 amORD - KIN
1 stop7h 21mSpirit Airlines
Deal found 10/28$360
This United Airlines deal was found by Cheapflights users on 10/30. 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.
jeu. 11/202:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
dim. 11/238:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
Deal found 10/30$380
This Delta deal was found by Cheapflights users on 10/30. 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. 11/259:00 amKIN - ORD
1 stop7h 26mDelta
jeu. 11/276:45 amORD - KIN
2 stops12h 15mDelta
Deal found 10/30$388
This United Airlines deal was found by Cheapflights users on 10/29. 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.
sam. 11/11:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
mer. 12/36:00 amORD - MBJ
1 stop7h 29mUnited Airlines
Deal found 10/29$393
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/252:24 pmKIN - ORD
1 stop9h 49mMultiple Airlines
mar. 12/24:22 pmORD - KIN
2 stops42h 52mMultiple Airlines
Deal found 10/28$397
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/257:30 amKIN - ORD
2 stops9h 35mAmerican Airlines
mar. 12/210:15 amORD - KIN
2 stops10h 58mAmerican Airlines
Deal found 10/28$402
This OneTravel deal was found by Cheapflights users on 10/29. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 12/121:19 pmKIN - ORD
1 stop7h 42mSpirit Airlines
mer. 12/315:00 amORD - KIN
1 stop6h 14mSpirit Airlines
Deal found 10/29$408

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 octobre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$287
(Priceline)

One-way from

$171
(Gotogate)

Popular in

January

Cheapest in

September

Good round-trip deal

$264 or less

Good one-way deal

$234 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. 13% potential increase in price ($75 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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 octobre 30, 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

jeu. 11/13

1:07 pm-11:06 pm

2 stops10h 59m

Chicago O'Hare Intl

dim. 11/16

5:10 am-12:02 pm

1 stop5h 52m

$319

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

ven. 12/12

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

ven. 1/2

8:42 am-1:46 pm

Nonstop4h 04m

$320

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

jeu. 11/13

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

dim. 11/16

8:42 am-1:46 pm

Nonstop4h 04m

$320

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

dim. 11/23

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

dim. 11/30

8:42 am-1:46 pm

Nonstop4h 04m

$320

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

ven. 1/9

2:16 pm-9:04 pm

1 stop7h 48m

Chicago O'Hare Intl

lun. 1/12

5:33 am-8:36 pm

1 stop14h 03m

$326

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

dim. 11/23

2:14 pm-5:50 pm

Nonstop4h 36m

Chicago O'Hare Intl

dim. 11/30

11:59 pm-2:59 pm

1 stop14h 00m

$330

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

mar. 11/25

2:24 pm-11:13 pm

1 stop9h 49m

Chicago O'Hare Intl

mar. 12/2

5:00 am-1:21 pm

1 stop7h 21m

$360

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

ven. 1/9

5:06 pm-11:25 pm

1 stop7h 19m

Chicago Midway

lun. 1/12

2:01 pm-12:05 pm

2 stops21h 04m

$385

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

mar. 11/25

9:00 am-4:46 pm

1 stop8h 46m

Chicago O'Hare Intl

jeu. 11/27

11:19 am-8:00 pm

1 stop7h 41m

$388

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

mer. 11/26

9:00 am-6:52 pm

1 stop10h 52m

Chicago O'Hare Intl

mer. 12/3

6:45 am-8:06 pm

2 stops12h 21m

$388

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 44 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, December is the cheapest month in which you can book a flight from Jamaica to Chicago (average of $251). Flying from Jamaica to Chicago in April is currently the most expensive (average of $440). 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 octobre 30, 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 octobre 30, 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
7,998 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!

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 United Airlines, with whom users have recently found tickets for as low as $203. However, be on the lookout for offers from Southwest and Delta, 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 American Airlines (85%), British Airways (82%) and United Airlines (0%).

  • What are the cheapest flights from Jamaica to Chicago?

    Looking for the cheapest flight from Jamaica to Chicago? While on average our users pay $378, our data indicates the cheapest price to be $203. The most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl), is priced around $320.

  • 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, December is the cheapest month in which you can book a flight from Jamaica to Chicago (average of $251). Flying from Jamaica to Chicago in April is currently the most expensive (average of $440). 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
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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Luis Munoz Marin Intl to Midway flights
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Luis Munoz Marin Intl to St. Louis flights
Oranjestad to O'Hare Intl flights
Nassau to O'Hare Intl flights
Santo Domingo to Midway flights
Montego Bay to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Nassau to Midway flights
Kingston to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
George Town to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Simpson Bay to Midway flights
Montego Bay to Midway flights
Roseau to O'Hare Intl flights
Aguadilla to O'Hare Intl flights
St. George's to St. Louis flights
Oranjestad to St. Louis flights
Vieques to O'Hare Intl flights
Nassau to St. Louis flights
Port of Spain 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
Culebra to O'Hare Intl flights
St. John's 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 octobre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$361FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$348Average$508FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$392Average$536FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$409Average$484FlexibilityNo cancel feeOn-time69%

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