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Jamaica

$106+ 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
Jan 8 — Jan 151
Thu 1/8
Thu 1/15
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 December 9, 2025.

This Priceline deal was found by Cheapflights users on 12/8. 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.
Mon 12/156:11 amORD - MBJ
1 stop7h 01mFrontier
Mon 12/223:47 pmMBJ - ORD
1 stop7h 37mFrontier
Deal found 12/8$362
This Priceline deal was found by Cheapflights users on 12/8. 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.
Mon 12/156:15 amMDW - MBJ
1 stop6h 57mFrontier
Mon 12/223:47 pmMBJ - MDW
1 stop7h 25mFrontier
Deal found 12/8$362
This Priceline deal was found by Cheapflights users on 12/8. 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.
Mon 12/156:11 amORD - MBJ
1 stop7h 01mFrontier
Sat 12/273:34 pmMBJ - ORD
1 stop8h 12mFrontier
Deal found 12/8$363
This Mytrip deal was found by Cheapflights users on 12/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:00 amORD - MBJ
1 stop25h 59mFrontier
Mon 12/2210:14 amMBJ - ORD
1 stop9h 19mFrontier
Deal found 12/7$367
This Mytrip deal was found by Cheapflights users on 12/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:12 amMDW - MBJ
1 stop25h 47mFrontier
Mon 12/223:47 pmMBJ - MDW
1 stop7h 25mFrontier
Deal found 12/7$367
This Gotogate deal was found by Cheapflights users on 12/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:00 amORD - MBJ
1 stop26h 57mFrontier
Wed 12/3110:24 amMBJ - ORD
1 stop13h 00mFrontier
Deal found 12/6$368
This Gotogate deal was found by Cheapflights users on 12/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/198:15 amMDW - MBJ
1 stop24h 42mFrontier
Wed 12/313:49 pmMBJ - MDW
1 stop7h 23mFrontier
Deal found 12/6$368
This Booking.com deal was found by Cheapflights users on 12/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/265:15 amORD - MBJ
1 stop29h 40mFrontier
Tue 12/303:47 pmMBJ - ORD
2 stops29h 19mFrontier
Deal found 12/9$374
This American Airlines deal was found by Cheapflights users on 12/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/810:15 amORD - MBJ
Nonstop4h 07mAmerican Airlines
Thu 12/113:12 pmMBJ - ORD
Nonstop4h 47mAmerican Airlines
Deal found 12/7$376
This American Airlines deal was found by Cheapflights users on 12/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:51 pmORD - MBJ
1 stop14h 21mAmerican Airlines
Thu 12/184:27 pmMBJ - ORD
Nonstop4h 37mAmerican Airlines
Deal found 12/8$381
This Priceline deal was found by Cheapflights users on 12/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:00 amORD - MBJ
1 stop25h 59mFrontier
Sun 12/214:16 pmMBJ - ORD
1 stop27h 17mFrontier
Deal found 12/7$392
This Frontier deal was found by Cheapflights users on 12/9. 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 12/9$392

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 December 9, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$353
(Cheapflightsfares)

One-way from

$106
(Cheapflightsfares)

Popular in

March

Cheapest in

January

Average price

$617

Good round-trip deal

$477 or less

Good one-way deal

$215 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. 5% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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.
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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 December 9, 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

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

Sat 1/24

7:30 pm-12:58 pm

1 stop16h 28m

Montego Bay Sangster Intl

Thu 1/29

3:12 pm-6:51 pm

Nonstop4h 39m

$381

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Thu 1/22

5:59 pm-11:33 am

2 stops16h 34m

Montego Bay Sangster Intl

Thu 1/29

2:34 pm-11:12 pm

1 stop9h 38m

$389

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Thu 1/1

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

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/3

5:59 pm-11:13 am

1 stop16h 14m

Montego Bay Sangster Intl

Thu 2/5

2:19 pm-9:00 pm

1 stop7h 41m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 1/27

5:30 am-12:54 pm

1 stop6h 24m

Montego Bay Sangster Intl

Tue 2/3

12:38 pm-11:56 pm

1 stop12h 18m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 1/5

6:15 am-2:40 pm

1 stop7h 25m

Montego Bay Sangster Intl

Wed 1/14

12:38 pm-7:35 pm

1 stop7h 57m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/3

5:30 am-12:54 pm

1 stop6h 24m

Montego Bay Sangster Intl

Fri 2/6

12:38 pm-9:00 pm

1 stop9h 22m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 2/2

7:59 pm-11:13 am

1 stop14h 14m

Montego Bay Sangster Intl

Wed 2/4

12:38 pm-7:21 pm

1 stop7h 43m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 2/1

6:00 am-3:20 pm

1 stop8h 20m

Montego Bay Sangster Intl

Fri 2/6

4:45 pm-10:22 pm

1 stop6h 37m

$391

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

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 $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 December 9, 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.

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 December 9, 2025.

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 Frontier, American Airlines, and Delta fly from Illinois to Jamaica in about 8h 31m. The time it takes to get you to your destination can typically vary by up to 7h 57m. There are 1709 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. American Airlines flights start at $164 while deals on Southwest start at $168 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 $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

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.
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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 December 9, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$174Average$414FlexibilityNo cancel feeOn-time65%
DeltaCheapest$186Average$709FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$356Average$606FlexibilityNo cancel feeOn-time69%
FrontierCheapest$370Average$662FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$433Average$676FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$549Average$724FlexibilityNo cancel feeOn-time63%

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