HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Jamaica

$113+ 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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
Dec 18 — Dec 251
Thu 12/18
Thu 12/25
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 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$337
(Spirit Airlines)

One-way from

$113
(Cheapflightsfares)

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. 5% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 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 18, 2025.

This Spirit Airlines deal was found by Cheapflights users on 11/17. 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 Spirit Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/85:00 amORD - KIN
1 stop6h 14mSpirit Airlines
Wed 12/101:19 pmKIN - ORD
1 stop7h 42mSpirit Airlines
Deal found 11/17$337
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/246:05 amORD - MBJ
1 stop7h 24mFrontier
Thu 1/13:47 pmMBJ - ORD
1 stop7h 37mFrontier
Deal found 11/17$356
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 12/102:49 pmMDW - MBJ
2 stops20h 21mMultiple Airlines
Mon 12/153:31 pmMBJ - MDW
1 stop18h 15mMultiple Airlines
Deal found 11/16$356
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 12/83:26 pmORD - MBJ
1 stop19h 44mSpirit Airlines
Thu 12/181:05 pmMBJ - ORD
1 stop6h 34mSpirit Airlines
Deal found 11/16$358
This Kiwi.com deal was found by Cheapflights users on 11/15. 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 stops19h 04mMultiple Airlines
Wed 12/241:05 pmMBJ - ORD
1 stop26h 57mMultiple Airlines
Deal found 11/15$360
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/128:42 pmMDW - MBJ
1 stop18h 09mMultiple Airlines
Tue 12/161:05 pmMBJ - MDW
2 stops20h 41mMultiple Airlines
Deal found 11/17$360
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/246:05 amORD - MBJ
1 stop7h 24mMultiple Airlines
Wed 1/73:05 pmMBJ - ORD
1 stop29h 12mMultiple Airlines
Deal found 11/17$361
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/246:05 amORD - MBJ
1 stop7h 24mMultiple Airlines
Thu 1/812:57 pmMBJ - ORD
1 stop8h 33mMultiple Airlines
Deal found 11/17$362
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/246:12 amMDW - MBJ
1 stop7h 17mFrontier
Wed 12/313:49 pmMBJ - MDW
1 stop7h 23mFrontier
Deal found 11/17$362
This American Airlines deal was found by Cheapflights users on 11/17. 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
Sat 12/133:12 pmMBJ - ORD
Nonstop4h 47mAmerican Airlines
Deal found 11/17$364
This Kiwi.com deal was found by Cheapflights users on 11/17. 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
1 stop21h 28mFrontier
Wed 12/243:49 pmMBJ - ORD
1 stop7h 35mFrontier
Deal found 11/17$365
This American Airlines deal was found by Cheapflights users on 11/17. 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 12/25:00 amORD - MBJ
1 stop7h 01mAmerican Airlines
Sat 12/63:12 pmMBJ - ORD
Nonstop4h 47mAmerican Airlines
Deal found 11/17$369

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 18, 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

Wed 12/10

2:49 pm-12:10 pm

2 stops20h 21m

Montego Bay Sangster Intl

Mon 12/15

3:31 pm-8:46 am

1 stop18h 15m

$356

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 2/6

5:01 pm-3:54 pm

1 stop21h 53m

Montego Bay Sangster Intl

Sat 2/14

4:51 pm-11:25 pm

1 stop7h 34m

$362

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 12/8

6:45 am-3:49 pm

1 stop8h 04m

Montego Bay Sangster Intl

Sat 12/13

3:12 pm-6:59 pm

Nonstop4h 47m

$369

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/17

5:00 am-1:39 pm

1 stop7h 39m

Montego Bay Sangster Intl

Wed 2/25

2:14 pm-6:00 pm

Nonstop4h 46m

$369

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

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 12/25

6:35 am-2:50 pm

1 stop7h 15m

Montego Bay Sangster Intl

Tue 12/30

2:12 pm-8:36 pm

1 stop7h 24m

$379

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 12/23

6:02 pm-12:47 pm

1 stop17h 45m

Montego Bay Sangster Intl

Mon 12/29

8:00 am-3:13 pm

1 stop8h 13m

$379

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 1/7

5:30 am-3:20 pm

1 stop8h 50m

Montego Bay Sangster Intl

Wed 1/14

12:38 pm-7:35 pm

1 stop7h 57m

$379

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Mon 2/23

6:00 am-3:29 pm

1 stop8h 29m

Montego Bay Sangster Intl

Thu 2/26

4:01 pm-8:52 am

1 stop17h 51m

$379

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 12/4

5:30 am-2:13 pm

1 stop7h 43m

Montego Bay Sangster Intl

Thu 12/11

2:29 pm-12:01 am

1 stop10h 32m

$379

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

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, 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 18, 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 Frontier, American Airlines, and Spirit Airlines fly from Illinois to Jamaica in about 8h 04m. The time it takes to get you to your destination can typically vary by up to 16h 51m. 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $119. Frontier flights start at $122 while deals on American Airlines start at $166 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
John F Kennedy Intl to Santiago de los Caballeros flights
Newark to Santo Domingo flights
John F Kennedy Intl to Punta Cana flights
Dulles Intl to Luis Munoz Marin Intl flights
LaGuardia to Luis Munoz Marin Intl flights
Newark to Punta Cana flights
Boston to Luis Munoz Marin Intl flights
O'Hare Intl to Luis Munoz Marin Intl flights
Baltimore to Luis Munoz Marin Intl flights
Reagan-National to Luis Munoz Marin Intl flights
Newark to Santiago de los Caballeros flights
Orlando to Luis Munoz Marin Intl flights
John F Kennedy Intl to Oranjestad flights
Philadelphia to Luis Munoz Marin Intl flights
Newark to Oranjestad flights
Atlanta to Luis Munoz Marin Intl flights
John F Kennedy Intl to Montego Bay flights
LaGuardia to Punta Cana flights
LaGuardia to Santo Domingo flights
O'Hare Intl to Punta Cana flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Hartford to Luis Munoz Marin Intl flights
Minneapolis to Luis Munoz Marin Intl flights
John F Kennedy Intl to Port of Spain flights
Dulles Intl to Punta Cana flights
Boston to Santo Domingo flights
Boston to Oranjestad flights
John F Kennedy Intl to Kingston flights
Tampa to Luis Munoz Marin Intl flights
Newark to Simpson Bay flights
Orlando to Punta Cana flights
Raleigh to Luis Munoz Marin Intl flights
Boston to Punta Cana flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Detroit to Luis Munoz Marin Intl flights
John F Kennedy Intl to Simpson Bay flights
LaGuardia to Oranjestad flights
John F Kennedy Intl to Nassau flights
John F Kennedy Intl to Saint Thomas Island flights
Hobby to Luis Munoz Marin Intl flights
Newark to Nassau flights
Newark to Saint Thomas Island flights
Fort Lauderdale to Santo Domingo flights
Miami to Santo Domingo flights
John F Kennedy Intl to Willemstad flights
Atlanta to Montego Bay flights
Newark to Montego Bay 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 18, 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.