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Jamaica

$115+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
Dec 24 — Dec 311
Wed 12/24
Wed 12/31
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 November 24, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$347
(Kiwi.com)

One-way from

$115
(CheapOair)

Popular in

March

Cheapest in

September

Average price

$551

Good round-trip deal

$421 or less

Good one-way deal

$195 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. 4% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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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 November 24, 2025.

This Priceline deal was found by Cheapflights users on 11/23. 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.
Mon 12/86:11 amORD - MBJ
1 stop7h 01mFrontier
Mon 12/153:31 pmMBJ - ORD
1 stop24h 41mFrontier
Deal found 11/23$358
This Priceline deal was found by Cheapflights users on 11/22. 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 12/174:01 pmORD - MBJ
1 stop21h 28mFrontier
Tue 12/233:47 pmMBJ - ORD
1 stop7h 37mFrontier
Deal found 11/22$359
This Kiwi.com deal was found by Cheapflights users on 11/22. 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 12/256:00 amORD - MBJ
1 stop7h 29mMultiple Airlines
Wed 1/73:05 pmMBJ - ORD
1 stop10h 11mMultiple Airlines
Deal found 11/22$363
This Frontier deal was found by Cheapflights users on 11/23. 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.
Thu 12/256:00 amORD - MBJ
1 stop7h 29mFrontier
Tue 12/303:47 pmMBJ - ORD
1 stop7h 37mFrontier
Deal found 11/23$366
This Frontier deal was found by Cheapflights users on 11/23. 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.
Thu 12/256:12 amMDW - MBJ
1 stop7h 17mFrontier
Tue 12/303:47 pmMBJ - MDW
1 stop7h 25mFrontier
Deal found 11/23$366
This Frontier deal was found by Cheapflights users on 11/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:12 amMDW - MBJ
1 stop7h 17mFrontier
Tue 12/233:47 pmMBJ - MDW
1 stop7h 25mFrontier
Deal found 11/24$367
This CheapOair deal was found by Cheapflights users on 11/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/185:00 amORD - MBJ
1 stop6h 05mSpirit Airlines
Mon 12/223:05 pmMBJ - ORD
2 stops10h 25mSpirit Airlines
Deal found 11/23$369
This Kiwi.com deal was found by Cheapflights users on 11/23. 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.
Mon 12/83:10 pmMDW - MBJ
2 stops20h 00mMultiple Airlines
Mon 12/153:31 pmMBJ - MDW
1 stop18h 15mMultiple Airlines
Deal found 11/23$372
This Kiwi.com deal was found by Cheapflights users on 11/22. 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.
Wed 12/174:01 pmORD - MBJ
2 stops43h 04mMultiple Airlines
Tue 12/233:47 pmMBJ - ORD
1 stop7h 37mMultiple Airlines
Deal found 11/22$374
This Mytrip deal was found by Cheapflights users on 11/23. 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.
Sat 12/137:20 amORD - MBJ
3 stops27h 50mSpirit Airlines
Tue 12/161:05 pmMBJ - ORD
1 stop7h 56mSpirit Airlines
Deal found 11/23$380
This KAYAK deal was found by Cheapflights users on 11/22. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:57 pmORD - MBJ
2 stops15h 08mSpirit Airlines
Thu 1/812:57 pmMBJ - ORD
1 stop7h 20mSpirit Airlines
Deal found 11/22$381
This Frontier deal was found by Cheapflights users on 11/22. 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.
Sat 12/206:10 amORD - MBJ
1 stop7h 19mFrontier
Tue 12/303:47 pmMBJ - ORD
1 stop7h 37mFrontier
Deal found 11/22$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 November 24, 2025.
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

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 1/25

10:07 am-12:02 pm

2 stops24h 55m

Montego Bay Sangster Intl

Thu 1/29

12:57 pm-7:17 pm

1 stop7h 20m

$357

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 2/21

6:00 am-3:31 pm

1 stop8h 31m

Montego Bay Sangster Intl

Sat 2/28

4:51 pm-11:25 pm

1 stop7h 34m

$362

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 1/8

8:27 pm-12:02 pm

2 stops14h 35m

Montego Bay Sangster Intl

Mon 2/2

12:57 pm-7:17 pm

1 stop7h 20m

$362

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 1/8

8:27 pm-12:02 pm

2 stops14h 35m

Montego Bay Sangster Intl

Sat 1/31

5:32 pm-2:02 pm

1 stop21h 30m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 1/7

5:00 am-12:05 pm

1 stop6h 05m

Montego Bay Sangster Intl

Sat 1/31

5:32 pm-10:47 am

2 stops18h 15m

$380

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Tue 12/23

6:05 am-2:50 pm

1 stop7h 45m

Montego Bay Sangster Intl

Tue 12/30

2:55 pm-10:16 pm

1 stop8h 21m

$391

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Sun 1/4

9:47 am-8:41 pm

1 stop9h 54m

Montego Bay Sangster Intl

Thu 1/8

4:05 pm-11:25 pm

1 stop8h 20m

$391

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Thu 12/25

6:00 am-2:13 pm

1 stop7h 13m

Montego Bay Sangster Intl

Tue 12/30

8:00 am-6:17 pm

1 stop11h 17m

$391

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Sun 12/21

6:05 am-2:50 pm

1 stop7h 45m

Montego Bay Sangster Intl

Sun 12/28

8:00 am-9:43 pm

1 stop14h 43m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 3/8

8:42 am-12:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Fri 3/13

1:48 pm-6:13 pm

Nonstop4h 25m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/22

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 $193). Flying from Illinois to Jamaica in March is currently the most expensive (average of $414). 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 November 24, 2025.

A simple way to save on the total cost of your ticket is to fly from Illinois to Jamaica in the afternoon. If you’re flexible enough to do this you can expect to save up to 61% on your trip compared to booking a flight in the evening.

What is the cheapest day to fly from Illinois to Jamaica?

Use this chart to determine the cheapest time to fly round-trip from Illinois to Jamaica. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Illinois to Jamaica flight should consider departing on Sunday at noon when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 Spirit Airlines, Frontier, and Delta fly from Illinois to Jamaica in about 7h 45m. The time it takes to get you to your destination can typically vary by up to 17h 10m. 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 $137. United Airlines flights start at $141 while deals on Southwest start at $146 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 $193). Flying from Illinois to Jamaica in March is currently the most expensive (average of $414). 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

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

Alternative routes for Illinois to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Luis Munoz Marin Intl flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santo Domingo flights
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Hobby to Luis Munoz Marin Intl flights
LaGuardia to Nassau flights
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John F Kennedy Intl to Saint Thomas Island flights
Atlanta to Punta Cana flights
Newark to Montego Bay flights
John F Kennedy Intl to Nassau flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Fort Lauderdale to Santo Domingo flights

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 November 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$186Average$721FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$194Average$426FlexibilityNo cancel feeOn-time65%
FrontierCheapest$333Average$662FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$373Average$626FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$433Average$676FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$549Average$724FlexibilityNo cancel feeOn-time63%

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