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$178+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Apr 14 — Apr 211
Tue 4/14
Tue 4/21
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 March 15, 2026.

This American Airlines deal was found by Cheapflights users on 3/11. 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.
Wed 6/102:30 pm
MBJ
-
ORD
Nonstop4h 45m
American Airlines
Sun 8/308:30 am
ORD
-
MBJ
Nonstop4h 01m
American Airlines
Deal found 3/11$281
This Southwest deal was found by Cheapflights users on 3/12. 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.
Sat 6/62:30 pm
MBJ
-
MDW
Nonstop4h 05m
Southwest
Sat 6/2710:10 am
MDW
-
MBJ
Nonstop3h 50m
Southwest
Deal found 3/12$281
This American Airlines deal was found by Cheapflights users on 3/11. 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.
Wed 5/131:15 pm
MBJ
-
ORD
Nonstop4h 40m
American Airlines
Sun 5/179:45 am
ORD
-
MBJ
1 stop5h 52m
American Airlines
Deal found 3/11$286
This United Airlines deal was found by Cheapflights users on 3/11. 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 5/122:40 pm
MBJ
-
ORD
1 stop17h 13m
United Airlines
Thu 5/287:40 pm
ORD
-
MBJ
1 stop19h 30m
United Airlines
Deal found 3/11$291
This United Airlines deal was found by Cheapflights users on 3/11. 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.
Wed 5/132:40 pm
MBJ
-
ORD
1 stop10h 47m
United Airlines
Mon 5/189:56 pm
ORD
-
MBJ
1 stop15h 34m
United Airlines
Deal found 3/11$292
This American Airlines deal was found by Cheapflights users on 3/11. 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 6/22:08 pm
MBJ
-
ORD
1 stop7h 21m
American Airlines
Tue 9/86:34 am
ORD
-
MBJ
1 stop7h 24m
American Airlines
Deal found 3/11$296
This American Airlines deal was found by Cheapflights users on 3/11. 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 6/22:55 pm
MBJ
-
ORD
1 stop9h 43m
American Airlines
Wed 9/28:30 am
ORD
-
MBJ
Nonstop4h 01m
American Airlines
Deal found 3/11$297
This American Airlines deal was found by Cheapflights users on 3/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:56 pm
MBJ
-
ORD
1 stop8h 42m
American Airlines
Wed 4/296:40 am
ORD
-
MBJ
1 stop7h 35m
American Airlines
Deal found 3/13$301
This American Airlines deal was found by Cheapflights users on 3/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1912:21 pm
MBJ
-
ORD
1 stop21h 51m
American Airlines
Tue 3/245:00 am
ORD
-
MBJ
1 stop6h 24m
American Airlines
Deal found 3/13$303
This United Airlines deal was found by Cheapflights users on 3/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/191:48 pm
MBJ
-
ORD
Nonstop4h 25m
United Airlines
Tue 3/248:42 am
ORD
-
MBJ
Nonstop4h 04m
United Airlines
Deal found 3/13$312
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Sat 6/64:12 pm
MBJ
-
ORD
1 stop7h 14m
United Airlines
Sat 6/278:40 am
ORD
-
MBJ
Nonstop4h 10m
United Airlines
Deal found 3/12$322
This United Airlines deal was found by Cheapflights users on 3/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/232:20 pm
MBJ
-
ORD
1 stop18h 47m
United Airlines
Fri 4/39:50 pm
ORD
-
MBJ
1 stop15h 40m
United Airlines
Deal found 3/13$332

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 March 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$281
(American Airlines)

One-way from

$178
(Super.com)

Popular in

March

Cheapest in

November

Average price

$786

Good round-trip deal

$301 or less

Good one-way deal

$192 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 ($79 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 15, 2026.
Use the filters below to find and compare flights from Jamaica to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 3/19

1:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Tue 3/24

8:10 pm-1:05 pm

1 stop16h 55m

$286

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 5/13

2:40 pm-12:45 am

1 stop10h 05m

Chicago O'Hare Intl

Sat 5/30

8:03 pm-3:26 pm

1 stop19h 23m

$291

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/16

12:36 pm-11:54 pm

1 stop11h 18m

Chicago O'Hare Intl

Tue 9/1

8:30 am-12:31 pm

Nonstop4h 01m

$292

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/14

2:40 pm-1:27 am

1 stop10h 47m

Chicago O'Hare Intl

Sat 5/30

8:40 am-12:50 pm

Nonstop4h 10m

$292

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 5/12

2:40 pm-11:15 pm

1 stop8h 35m

Chicago O'Hare Intl

Thu 5/28

9:40 pm-3:10 pm

1 stop17h 30m

$292

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 6/2

4:12 pm-4:52 pm

1 stop24h 40m

Chicago O'Hare Intl

Sat 9/12

6:30 am-1:30 pm

1 stop7h 00m

$292

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 5/19

3:20 pm-11:34 pm

1 stop8h 14m

Chicago O'Hare Intl

Mon 8/17

6:34 am-1:58 pm

1 stop7h 24m

$296

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 5/13

2:40 pm-11:15 pm

1 stop8h 35m

Chicago O'Hare Intl

Wed 5/27

6:30 am-1:30 pm

1 stop7h 00m

$296

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 3/23

2:20 pm-9:07 am

1 stop18h 47m

Chicago O'Hare Intl

Fri 4/3

9:50 pm-1:30 pm

1 stop15h 40m

$332

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 6/2

4:12 pm-8:47 am

1 stop16h 35m

Chicago O'Hare Intl

Fri 9/4

9:30 pm-1:30 pm

1 stop16h 00m

$383

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/13

Showing 1-10 of 51 resultsSorted by cheapest first
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6

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, April is the cheapest month in which you can book a flight from Jamaica to Chicago (average of $184). Flying from Jamaica to Chicago in January is currently the most expensive (average of $448). 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 March 15, 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.

Weekly flight availability from Jamaica to Chicago

Explore weekly flight availability from Jamaica to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 15, 2026.

The most flights from JM0 to CHI are scheduled on a Saturday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

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 March 15, 2026.
Peruse reviews from past customers who have flown with 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.
American Airlines
7.1
Good
11,472 reviews

Crew

7.9

Overall

7.1

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes
American Airlines
7.1
Good
11,472 reviews
American Airlines
7.1
Good
11,472 reviews

Crew

7.9

Overall

7.1

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes

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 Hawaiian Airlines, with whom users have recently found tickets for as low as $156. However, be on the lookout for offers from United Airlines and Alaska 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 cheapest flights from Jamaica to Chicago?

    Looking for the cheapest flight from Jamaica to Chicago? While on average our users pay $329, our data indicates the cheapest price to be $172. The most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl), is priced around $286.

  • 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, April is the cheapest month in which you can book a flight from Jamaica to Chicago (average of $184). Flying from Jamaica to Chicago in January is currently the most expensive (average of $448). 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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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 March 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$146Average$371FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$305Average$500FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$306Average$469FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$392Average$536FlexibilityNo cancel feeOn-time63%

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