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Jamaica

$117+ Cheap flights from Illinois to Jamaica

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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
Mar 28 — Apr 41
Sat 3/28
Sat 4/4
1 adult, Economy
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Cheap flight deals from Illinois to Jamaica

Cheapest flights from Illinois to Jamaica
Explore the most affordable flight options available from Illinois to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 26, 2026.

This Delta deal was found by Cheapflights users on 2/24. 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.
Tue 5/127:15 am
STL
-
MBJ
1 stop8h 19m
Delta
Tue 5/194:59 pm
MBJ
-
STL
1 stop15h 19m
Delta
Deal found 2/24$282
This American Airlines deal was found by Cheapflights users on 2/26. 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 5/128:05 am
ORD
-
MBJ
Nonstop4h 08m
American Airlines
Sun 5/171:15 pm
MBJ
-
ORD
Nonstop4h 40m
American Airlines
Deal found 2/26$293
This American Airlines deal was found by Cheapflights users on 2/24. 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 8/18:53 pm
ORD
-
MBJ
1 stop18h 27m
American Airlines
Thu 8/62:00 pm
MBJ
-
ORD
Nonstop4h 30m
American Airlines
Deal found 2/24$294
This American Airlines deal was found by Cheapflights users on 2/25. 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 4/157:15 am
ORD
-
MBJ
1 stop6h 10m
American Airlines
Sun 4/191:15 pm
MBJ
-
ORD
Nonstop4h 40m
American Airlines
Deal found 2/25$297
This United Airlines deal was found by Cheapflights users on 2/24. 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 3/118:42 am
ORD
-
MBJ
Nonstop4h 04m
United Airlines
Wed 3/181:48 pm
MBJ
-
ORD
Nonstop4h 25m
United Airlines
Deal found 2/24$298
This American Airlines deal was found by Cheapflights users on 2/25. 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 5/98:46 pm
ORD
-
MBJ
1 stop12h 27m
American Airlines
Fri 5/152:29 pm
MBJ
-
ORD
1 stop25h 52m
American Airlines
Deal found 2/25$299
This American Airlines deal was found by Cheapflights users on 2/24. 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.
Mon 3/235:28 pm
ORD
-
MBJ
1 stop15h 39m
American Airlines
Thu 3/2610:07 am
MBJ
-
ORD
1 stop22h 46m
American Airlines
Deal found 2/24$300
This American Airlines deal was found by Cheapflights users on 2/25. 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 4/168:46 pm
ORD
-
MBJ
1 stop12h 27m
American Airlines
Wed 4/2210:17 am
MBJ
-
ORD
1 stop13h 37m
American Airlines
Deal found 2/25$302
This American Airlines deal was found by Cheapflights users on 2/25. 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.
Sun 5/108:05 am
ORD
-
MBJ
Nonstop4h 08m
American Airlines
Sun 5/173:20 pm
MBJ
-
ORD
1 stop16h 19m
American Airlines
Deal found 2/25$303
This American Airlines deal was found by Cheapflights users on 2/25. 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 4/308:05 am
ORD
-
MBJ
Nonstop4h 08m
American Airlines
Tue 5/511:16 am
MBJ
-
ORD
1 stop23h 42m
American Airlines
Deal found 2/25$304
This FlightHub deal was found by Cheapflights users on 2/26. 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.
Tue 4/145:05 am
ORD
-
MBJ
1 stop6h 00m
Spirit Airlines
Wed 4/2212:00 pm
MBJ
-
ORD
2 stops20h 03m
Spirit Airlines
Deal found 2/26$305
This Kiwi.com deal was found by Cheapflights users on 2/25. 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.
Tue 4/211:27 pm
ORD
-
MBJ
1 stop21h 32m
Multiple Airlines
Sat 4/2512:00 pm
MBJ
-
ORD
1 stop9h 17m
Multiple Airlines
Deal found 2/25$306

Find flight deals from Illinois to Jamaica

Keep the following information in mind while searching for Illinois to Jamaica flight deals. Data was last updated February 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$282
(Delta)

One-way from

$117
(Delta)

Popular in

June

Cheapest in

January

Average price

$546

Good round-trip deal

$464 or less

Good one-way deal

$180 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
Search Deals
From Illinois to Jamaica
Search Deals
One-way flight from Illinois to Jamaica
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Illinois to Jamaica.
Search Deals
Price to beat on a one-way flight from Illinois to Jamaica.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Jamaica 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 February 26, 2026.
Use the filters below to find and compare flights from Illinois to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 4/18

5:48 am-1:30 pm

1 stop7h 42m

Montego Bay Sangster Intl

Sat 4/25

1:52 pm-6:15 pm

Nonstop4h 23m

$302

EvansvilleMontego Bay

EVV - MBJ

EVVMBJ

Evansville Dress Regional

Sat 4/25

6:23 pm-12:13 pm

1 stop17h 50m

Montego Bay Sangster Intl

Wed 4/29

1:15 pm-11:54 pm

1 stop10h 39m

$312

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 4/5

8:40 am-12:50 pm

Nonstop4h 10m

Montego Bay Sangster Intl

Thu 4/9

1:52 pm-6:15 pm

Nonstop4h 23m

$317

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 4/16

8:40 am-12:50 pm

Nonstop4h 10m

Montego Bay Sangster Intl

Mon 4/20

4:12 pm-11:43 pm

1 stop7h 31m

$382

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 4/5

8:05 am-12:11 pm

Nonstop4h 06m

Montego Bay Sangster Intl

Thu 4/9

10:17 am-11:54 pm

1 stop13h 37m

$392

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 3/14

6:10 pm-11:35 am

1 stop17h 25m

Kingston Norman Manley

Wed 3/18

12:32 pm-11:17 pm

1 stop10h 45m

$415

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Tue 5/19

6:00 am-1:30 pm

1 stop7h 30m

Montego Bay Sangster Intl

Tue 5/26

4:12 pm-12:11 pm

2 stops19h 59m

$421

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Tue 5/12

5:15 pm-11:26 am

2 stops18h 11m

Montego Bay Sangster Intl

Mon 5/18

12:51 pm-9:29 am

2 stops20h 38m

$424

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Mon 5/18

8:15 pm-1:30 pm

2 stops17h 15m

Montego Bay Sangster Intl

Sun 5/24

4:33 pm-8:41 am

2 stops16h 08m

$424

MolineMontego Bay

MLI - MBJ

MLIMBJ

Moline Quad-City

Sat 5/2

6:50 pm-1:30 pm

2 stops18h 40m

Montego Bay Sangster Intl

Wed 5/6

2:40 pm-1:54 pm

2 stops23h 14m

$432

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/24

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Illinois to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Illinois 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 Illinois to Jamaica

What is the cheapest month to book a flight from Illinois to Jamaica?

Currently, January is the cheapest month in which you can book a flight from Illinois to Jamaica (average of $95). Flying from Illinois to Jamaica in August is currently the most expensive (average of $384). 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 IL to JM?

Find hourly flight availability from Illinois to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 26, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Jamaica as you normally would.

Weekly flight availability from Illinois to Jamaica

Explore weekly flight availability from Illinois to Jamaica. 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 February 26, 2026.

The most flights from USIL to JM0 are scheduled on a Monday (1 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 Illinois to Jamaica. 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 Illinois to Jamaica?

    Airlines like United Airlines, American Airlines, and Spirit Airlines fly from Illinois to Jamaica in about 7h 42m. The time it takes to get you to your destination can typically vary by up to 10h 08m. There are 1724 mi between Illinois and Jamaica. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Illinois to Jamaica one-way?

    To fly one-way, consider booking your trip with Hawaiian Airlines, which is currently one of the cheapest options available, starting at $106. United Airlines flights start at $160 while deals on American Airlines start at $160 one-way.

  • Can I find deals for flights from Illinois to Jamaica that include hotel bookings?

    Yes. In addition to deals on Illinois to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Jamaica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Jamaica.

  • Can I find deals for business class flights from Illinois to Jamaica?

    Yes. Cheapflights offers flight deals from Illinois to Jamaica 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 Illinois to Jamaica?

    Currently, January is the cheapest month in which you can book a flight from Illinois to Jamaica (average of $95). Flying from Illinois to Jamaica in August is currently the most expensive (average of $384). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Illinois to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Illinois to Jamaica

Discover the top 6 airlines that operate flights from Illinois to Jamaica. 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 February 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$100Average$453FlexibilityNo cancel feeOn-time65%
FrontierCheapest$144Average$662FlexibilityNo cancel feeOn-time62%
DeltaCheapest$178Average$601FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$356Average$577FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$404Average$668FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$518Average$693FlexibilityNo cancel feeOn-time63%

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