HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$168+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Jun 2 — Jun 91
Tue 6/2
Tue 6/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Jamaica to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 May 3, 2026.

This American Airlines deal was found by Cheapflights users on 4/28. 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.
Thu 5/282:30 pm
MBJ
-
ORD
Nonstop4h 45m
American Airlines
Mon 8/319:10 am
ORD
-
MBJ
Nonstop4h 07m
American Airlines
Deal found 4/28$281
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Thu 5/142:40 pm
MBJ
-
ORD
1 stop10h 47m
United Airlines
Sat 9/127:45 pm
ORD
-
MBJ
1 stop15h 58m
United Airlines
Deal found 4/29$290
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Fri 5/84:12 pm
MBJ
-
ORD
1 stop15h 14m
United Airlines
Fri 5/159:56 pm
ORD
-
MBJ
1 stop15h 34m
United Airlines
Deal found 4/29$296
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Wed 8/262:20 pm
MBJ
-
ORD
Nonstop4h 45m
American Airlines
Sat 8/299:10 am
ORD
-
MBJ
Nonstop4h 07m
American Airlines
Deal found 4/29$301
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Thu 5/141:15 pm
MBJ
-
ORD
Nonstop4h 40m
American Airlines
Sat 9/128:44 pm
ORD
-
MBJ
1 stop12h 26m
American Airlines
Deal found 4/29$306
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 5/62:40 pm
MBJ
-
ORD
1 stop8h 35m
United Airlines
Fri 5/154:25 pm
ORD
-
MBJ
1 stop22h 45m
United Airlines
Deal found 4/30$311
This American Airlines deal was found by Cheapflights users on 5/3. 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 5/164:37 pm
MBJ
-
ORD
1 stop7h 48m
American Airlines
Mon 5/188:05 am
ORD
-
MBJ
Nonstop4h 08m
American Airlines
Deal found 5/3$312
This United Airlines deal was found by Cheapflights users on 5/3. 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 5/62:40 pm
MBJ
-
ORD
1 stop10h 47m
United Airlines
Sat 8/156:30 am
ORD
-
MBJ
1 stop7h 00m
United Airlines
Deal found 5/3$316
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:17 pm
MBJ
-
ORD
1 stop7h 07m
American Airlines
Wed 9/29:10 am
ORD
-
MBJ
Nonstop4h 07m
American Airlines
Deal found 4/30$317
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Wed 5/134:12 pm
MBJ
-
ORD
1 stop7h 32m
United Airlines
Fri 9/49:30 pm
ORD
-
MBJ
1 stop16h 00m
United Airlines
Deal found 4/29$324
This Priceline deal was found by Cheapflights users on 4/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:26 pm
MBJ
-
MDW
1 stop8h 45m
Frontier
Sat 8/296:00 am
MDW
-
MBJ
1 stop6h 21m
Frontier
Deal found 4/29$348
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Fri 6/56:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Deal found 4/29$376

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 May 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$281
(American Airlines)

One-way from

$168
(Priceline)

Popular in

March

Cheapest in

July

Average price

$486

Good round-trip deal

$316 or less

Good one-way deal

$224 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. 20% potential increase in price ($121 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 May 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 May 3, 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

Sun 7/19

4:33 pm-12:45 am

1 stop8h 12m

Chicago O'Hare Intl

Fri 7/24

9:40 pm-3:26 pm

1 stop17h 46m

$296

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/23

4:33 pm-10:20 am

1 stop17h 47m

Chicago O'Hare Intl

Sat 5/30

8:40 am-3:10 pm

1 stop6h 30m

$296

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 6/2

4:12 pm-7:27 am

1 stop15h 15m

Chicago O'Hare Intl

Fri 6/5

9:40 pm-3:10 pm

1 stop17h 30m

$296

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/23

2:40 pm-12:45 am

1 stop10h 05m

Chicago O'Hare Intl

Thu 7/23

9:40 pm-3:10 pm

1 stop17h 30m

$312

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 6/2

4:12 pm-7:27 am

1 stop15h 15m

Chicago O'Hare Intl

Sat 6/20

6:30 am-3:10 pm

1 stop8h 40m

$312

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/16

4:12 pm-7:26 am

1 stop15h 14m

Chicago O'Hare Intl

Fri 5/29

9:55 pm-3:10 pm

1 stop17h 15m

$316

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 6/17

4:12 pm-11:26 pm

1 stop7h 14m

Chicago O'Hare Intl

Sun 6/21

6:30 am-3:10 pm

1 stop8h 40m

$316
Quickest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 5/29

5:17 pm-12:24 am

1 stop7h 07m

Chicago O'Hare Intl

Wed 9/2

9:10 am-1:17 pm

Nonstop4h 07m

$317

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 5/13

4:12 pm-11:44 pm

1 stop7h 32m

Chicago O'Hare Intl

Fri 9/4

9:30 pm-1:30 pm

1 stop16h 00m

$324

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 8/26

1:26 pm-10:11 pm

1 stop8h 45m

Chicago Midway

Sat 8/29

6:00 am-12:21 pm

1 stop6h 21m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 57 resultsSorted by cheapest first
1
2
3
...
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 $146). Flying from Jamaica to Chicago in January is currently the most expensive (average of $397). 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 May 3, 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 May 3, 2026.

The most flights from JM0 to CHI are scheduled on a Saturday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 45m. 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 $185. However, be on the lookout for offers from Spirit Airlines 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 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 (82%), American Airlines (78%) and United Airlines (65%).

  • What are the cheapest flights from Jamaica to Chicago?

    Looking for the cheapest flight from Jamaica to Chicago? While on average our users pay $387, our data indicates the cheapest price to be $182. The most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl), is priced around $312.

  • 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 $146). Flying from Jamaica to Chicago in January is currently the most expensive (average of $397). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 May 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$281Average$409FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$281Average$463FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$281Average$486FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$391Average$406FlexibilityNo cancel feeOn-time65%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights