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Jamaica

$98+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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Cheap flight deals from Illinois to Jamaica

Keep the following information in mind while searching for Illinois to Jamaica flight deals. Data was last updated January 8, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$344
(Kiwi.com)

One-way from

$98
(Super.com)

Popular in

June

Cheapest in

January

Average price

$532

Good round-trip deal

$432 or less

Good one-way deal

$242 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
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From Illinois to Jamaica
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One-way flight from Illinois to Jamaica
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Highest demand for flights based on searches. 5% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Illinois to Jamaica.
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Price to beat on a one-way flight from Illinois to Jamaica.
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Find 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 January 8, 2026.

This Priceline deal was found by Cheapflights users on 1/8. 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 2/118:17 pmSTL - MBJ
1 stop16h 36mFrontier
Thu 2/193:08 pmMBJ - STL
1 stop16h 43mFrontier
Deal found 1/8$324
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Sat 2/218:17 pmSTL - MBJ
1 stop12h 00mMultiple Airlines
Sat 2/2812:40 pmMBJ - STL
2 stops12h 19mMultiple Airlines
Deal found 1/6$344
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
Thu 2/58:43 pmORD - KIN
1 stop14h 29mMultiple Airlines
Thu 2/121:17 pmKIN - ORD
1 stop11h 07mMultiple Airlines
Deal found 1/7$350
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
Thu 1/292:52 pmORD - KIN
1 stop20h 20mMultiple Airlines
Mon 2/21:17 pmKIN - ORD
1 stop23h 05mMultiple Airlines
Deal found 1/7$356
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Sat 1/315:32 pmORD - KIN
1 stop17h 40mSpirit Airlines
Fri 2/61:17 pmKIN - ORD
1 stop7h 21mSpirit Airlines
Deal found 1/6$359
This Cheapflightsfares deal was found by Cheapflights users on 1/7. 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.
Thu 2/55:32 pmORD - KIN
1 stop17h 40mSpirit Airlines
Thu 2/121:17 pmKIN - ORD
1 stop11h 30mSpirit Airlines
Deal found 1/7$364
This Air Canada deal was found by Cheapflights users on 1/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/131:00 pmSTL - MBJ
2 stops22h 20mAir Canada
Sat 6/2012:30 pmMBJ - STL
1 stop23h 51mAir Canada
Deal found 1/5$379
This Kiwi.com deal was found by Cheapflights users on 1/5. 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.
Sun 2/154:43 pmORD - KIN
1 stop18h 32mMultiple Airlines
Thu 2/191:17 pmKIN - ORD
1 stop11h 07mMultiple Airlines
Deal found 1/5$381
This Copa Airlines deal was found by Cheapflights users on 1/6. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/2711:51 pmORD - MBJ
1 stop10h 24mCopa Airlines
Sat 1/3112:17 pmMBJ - ORD
1 stop13h 07mCopa Airlines
Deal found 1/6$384
This Orbitz deal was found by Cheapflights users on 1/6. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:40 amORD - MBJ
2 stops26h 40mAir Canada
Sun 10/251:55 pmMBJ - ORD
2 stops30h 21mAir Canada
Deal found 1/6$385
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
Fri 2/205:15 amORD - MBJ
1 stop5h 47mSpirit Airlines
Sun 3/11:00 pmMBJ - ORD
1 stop23h 22mSpirit Airlines
Deal found 1/7$386
This Cheapflightsfares deal was found by Cheapflights users on 1/8. 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.
Thu 1/295:32 pmORD - KIN
1 stop17h 40mSpirit Airlines
Mon 2/21:17 pmKIN - ORD
1 stop11h 30mSpirit Airlines
Deal found 1/8$386

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 January 8, 2026.
Use the filters below to find and compare flights from Illinois to Jamaica that are best for you.

Fly from

Illinois

Fly to

Jamaica

Route

Depart

Return

Price

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Wed 2/11

8:17 pm-1:53 pm

1 stop16h 36m

Montego Bay Sangster Intl

Thu 2/19

3:08 pm-12:27 am

2 stops34h 19m

$359

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Sat 6/13

1:00 pm-11:20 am

2 stops22h 20m

Montego Bay Sangster Intl

Sat 6/20

12:30 pm-12:21 pm

1 stop23h 51m

$379

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Wed 2/18

6:10 am-2:40 pm

1 stop7h 30m

Montego Bay Sangster Intl

Wed 2/25

2:19 pm-11:36 pm

1 stop10h 17m

$392

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Sat 2/7

7:10 am-3:20 pm

1 stop7h 10m

Montego Bay Sangster Intl

Sat 2/14

2:16 pm-8:43 pm

1 stop7h 27m

$392

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 3/2

6:00 am-12:53 pm

1 stop5h 53m

Montego Bay Sangster Intl

Wed 3/4

12:20 pm-5:45 pm

1 stop6h 25m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 2/25

6:00 am-12:53 pm

1 stop5h 53m

Montego Bay Sangster Intl

Wed 3/4

4:44 pm-10:31 pm

1 stop6h 47m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/23

6:40 pm-11:10 am

1 stop15h 30m

Montego Bay Sangster Intl

Tue 3/3

4:44 pm-10:33 pm

1 stop6h 49m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/23

6:00 am-3:19 pm

1 stop8h 19m

Montego Bay Sangster Intl

Wed 2/25

4:44 pm-10:31 pm

1 stop6h 47m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 2/18

6:00 am-3:19 pm

1 stop8h 19m

Montego Bay Sangster Intl

Tue 3/3

2:19 pm-10:33 pm

1 stop9h 14m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 2/17

6:40 pm-11:10 am

1 stop15h 30m

Montego Bay Sangster Intl

Fri 2/27

12:20 pm-5:45 pm

1 stop6h 25m

$396

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 60 results
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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 March is currently the most expensive (average of $408). 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 January 8, 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.

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 Frontier, Air Canada, and Delta fly from Illinois to Jamaica in about 7h 30m. The time it takes to get you to your destination can typically vary by up to 14h 50m. There are 1585 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $98. United Airlines flights start at $157 while deals on American Airlines start at $164 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 March is currently the most expensive (average of $408). 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$168Average$417FlexibilityNo cancel feeOn-time65%
DeltaCheapest$186Average$706FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$341Average$662FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$356Average$607FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$429Average$666FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$549Average$724FlexibilityNo cancel feeOn-time63%

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