HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Jamaica

$97+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to Jamaica 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 Illinois to Jamaica

Keep the following information in mind while searching for Illinois to Jamaica flight deals. Data was last updated November 13, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$342
(Cheapflightsfares)

One-way from

$97
(Super.com)

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.
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. 4% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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.
Search Deals

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 13, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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.
Tue 11/255:00 amORD - KIN
1 stop7h 21mSpirit Airlines
Sat 12/131:19 pmKIN - ORD
1 stop7h 42mSpirit Airlines
Deal found 11/11$342
This Mytrip deal was found by Cheapflights users on 11/12. 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.
Tue 12/165:00 amORD - MBJ
1 stop6h 10mSpirit Airlines
Wed 12/243:05 pmMBJ - ORD
2 stops10h 25mSpirit Airlines
Deal found 11/12$356
This Priceline deal was found by Cheapflights users on 11/11. 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.
Tue 12/25:00 amORD - MBJ
1 stop6h 02mMultiple Airlines
Wed 12/102:15 pmMBJ - ORD
2 stops22h 03mMultiple Airlines
Deal found 11/11$357
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/136:11 amORD - MBJ
2 stops28h 59mMultiple Airlines
Tue 12/161:05 pmMBJ - ORD
1 stop7h 56mMultiple Airlines
Deal found 11/12$358
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/266:00 amORD - MBJ
1 stop7h 29mMultiple Airlines
Thu 1/812:57 pmMBJ - ORD
2 stops12h 45mMultiple Airlines
Deal found 11/12$359
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/268:00 amMDW - MBJ
2 stops24h 57mFrontier
Tue 12/303:47 pmMBJ - MDW
1 stop22h 34mFrontier
Deal found 11/12$360
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/266:00 amORD - MBJ
1 stop7h 29mFrontier
Mon 1/53:47 pmMBJ - ORD
1 stop20h 48mFrontier
Deal found 11/12$362
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/1112:04 pmSTL - MBJ
1 stop26h 34mMultiple Airlines
Fri 12/193:05 pmMBJ - STL
1 stop8h 28mMultiple Airlines
Deal found 11/10$363
This United Airlines deal was found by Cheapflights users on 11/11. 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 12/48:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
Mon 12/82:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
Deal found 11/11$364
This Yatra.com deal was found by Cheapflights users on 11/11. 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 Yatra.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/16:00 amMDW - MBJ
1 stop7h 11mDelta
Sun 12/213:38 pmMBJ - MDW
1 stop7h 44mDelta
Deal found 11/11$364
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/145:00 amORD - MBJ
1 stop6h 10mMultiple Airlines
Sun 1/185:06 pmMBJ - ORD
1 stop8h 06mMultiple Airlines
Deal found 11/11$366
This EaseMyTrip deal was found by Cheapflights users on 11/11. 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 EaseMyTrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/12:35 pmORD - MBJ
2 stops22h 38mDelta
Sun 12/218:00 amMBJ - ORD
1 stop17h 02mDelta
Deal found 11/11$367

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 13, 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

Thu 12/4

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Mon 12/8

2:48 pm-6:13 pm

Nonstop4h 25m

$364

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 12/8

6:00 am-2:29 pm

1 stop7h 29m

Montego Bay Sangster Intl

Sat 12/13

2:48 pm-6:13 pm

Nonstop4h 25m

$369

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 11/28

5:23 am-2:11 pm

1 stop7h 48m

Montego Bay Sangster Intl

Thu 12/4

5:58 pm-8:39 am

1 stop15h 41m

$371

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 11/25

5:00 am-1:21 pm

1 stop7h 21m

Kingston Norman Manley

Sat 12/13

1:19 pm-9:48 pm

2 stops9h 29m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 11/28

6:00 am-2:11 pm

1 stop7h 11m

Montego Bay Sangster Intl

Tue 12/2

5:58 pm-9:54 am

1 stop16h 56m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 1/12

5:00 am-1:00 pm

1 stop7h 00m

Montego Bay Sangster Intl

Fri 1/23

2:00 pm-9:00 pm

1 stop8h 00m

$379

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Fri 12/5

7:05 am-4:33 pm

1 stop8h 28m

Montego Bay Sangster Intl

Tue 12/9

2:29 pm-9:57 pm

1 stop8h 28m

$379

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Fri 12/26

6:35 pm-2:05 pm

2 stops18h 30m

Montego Bay Sangster Intl

Wed 12/31

2:48 pm-9:43 pm

1 stop7h 55m

$379

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Thu 1/15

9:59 am-8:36 pm

1 stop9h 37m

Montego Bay Sangster Intl

Tue 1/20

12:38 pm-11:39 pm

1 stop12h 01m

$379

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Sat 1/24

6:30 am-4:12 pm

2 stops8h 42m

Montego Bay Sangster Intl

Sat 1/31

3:55 pm-11:59 pm

1 stop9h 04m

$379

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 60 results
1
2
3
...
6

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, February is the cheapest month in which you can book a flight from Illinois to Jamaica (average of $258). 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 13, 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 November 13, 2025.

The most flights from USIL to JM0 are scheduled on a Wednesday (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 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, Delta, and Spirit Airlines fly from Illinois to Jamaica in about 4h 04m. The time it takes to get you to your destination can typically vary by up to 3h 44m. 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 Frontier, which is currently one of the cheapest options available, starting at $117. United Airlines flights start at $161 while deals on Delta start at $165 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, February is the cheapest month in which you can book a flight from Illinois to Jamaica (average of $258). 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
Newark to Santo Domingo flights
Dulles Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Punta Cana flights
LaGuardia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santiago de los Caballeros flights
O'Hare Intl to Luis Munoz Marin Intl flights
Newark to Oranjestad flights
Newark to Santiago de los Caballeros flights
Newark to Punta Cana flights
Orlando to Luis Munoz Marin Intl flights
Reagan-National to Luis Munoz Marin Intl flights
Boston to Luis Munoz Marin Intl flights
John F Kennedy Intl to Oranjestad flights
O'Hare Intl to Punta Cana flights
Atlanta to Luis Munoz Marin Intl flights
LaGuardia to Punta Cana flights
LaGuardia to Santo Domingo flights
Baltimore to Luis Munoz Marin Intl flights
Boston to Santo Domingo flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Hartford to Luis Munoz Marin Intl flights
Tampa to Luis Munoz Marin Intl flights
Philadelphia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Montego Bay flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
John F Kennedy Intl to Kingston flights
Boston to Oranjestad flights
Orlando to Punta Cana flights
John F Kennedy Intl to Port of Spain flights
Minneapolis to Luis Munoz Marin Intl flights
Raleigh to Luis Munoz Marin Intl flights
Newark to Simpson Bay flights
Dulles Intl to Punta Cana flights
LaGuardia to Oranjestad flights
Detroit to Luis Munoz Marin Intl flights
Newark to Montego Bay flights
Newark to Saint Thomas Island flights
John F Kennedy Intl to Nassau flights
John F Kennedy Intl to Saint Thomas Island flights
John F Kennedy Intl to Simpson Bay flights
Miami to Luis Munoz Marin Intl flights
Newark to Providenciales flights
Atlanta to Montego Bay flights
Newark to Nassau flights
Hobby to Luis Munoz Marin Intl flights
Miami to Santo Domingo 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 13, 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%

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.