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Jamaica

$99+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
Nov 9 — Nov 161
Sun 11/9
Sun 11/16
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 October 10, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$333
(Cheapflightsfares)

One-way from

$99
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$579

Good round-trip deal

$427 or less

Good one-way deal

$201 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. 3% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 10, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:59 pmORD - KIN
1 stop17h 14mSpirit Airlines
Sat 12/131:28 pmKIN - ORD
1 stop11h 14mSpirit Airlines
Deal found 10/9$333
This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
Wed 10/297:43 pmORD - KIN
1 stop15h 26mSpirit Airlines
Mon 11/31:06 pmKIN - ORD
1 stop21h 41mSpirit Airlines
Deal found 10/7$352
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1110:52 amORD - KIN
1 stop24h 09mSpirit Airlines
Fri 12/51:28 pmKIN - ORD
1 stop20h 55mSpirit Airlines
Deal found 10/8$354
This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/110:15 amORD - MBJ
Nonstop4h 13mAmerican Airlines
Fri 12/52:30 pmMBJ - ORD
Nonstop4h 47mAmerican Airlines
Deal found 10/9$356
This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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.
Sat 10/187:15 pmSTL - MBJ
1 stop15h 45mSpirit Airlines
Sat 10/2512:09 pmMBJ - STL
1 stop6h 01mSpirit Airlines
Deal found 10/8$358
This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/259:45 pmORD - MBJ
1 stop16h 30mAmerican Airlines
Wed 10/291:50 pmMBJ - ORD
Nonstop4h 33mAmerican Airlines
Deal found 10/9$359
This Cheapflightsfares deal was found by Cheapflights users on 10/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:59 pmORD - KIN
1 stop17h 14mSpirit Airlines
Wed 12/101:28 pmKIN - ORD
1 stop8h 32mSpirit Airlines
Deal found 10/9$360
This American Airlines deal was found by Cheapflights users on 10/8. 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 11/17:05 pmORD - MBJ
1 stop15h 07mAmerican Airlines
Thu 11/63:13 pmMBJ - ORD
Nonstop4h 41mAmerican Airlines
Deal found 10/8$361
This Booking.com deal was found by Cheapflights users on 10/7. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/165:50 pmORD - MBJ
1 stop20h 46mMultiple Airlines
Wed 10/2212:09 pmMBJ - ORD
1 stop6h 29mMultiple Airlines
Deal found 10/7$362
This Priceline deal was found by Cheapflights users on 10/7. 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.
Tue 11/115:10 amORD - MBJ
1 stop5h 52mMultiple Airlines
Tue 11/182:40 pmMBJ - ORD
2 stops23h 11mMultiple Airlines
Deal found 10/7$363
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1110:52 amORD - KIN
1 stop24h 09mSpirit Airlines
Tue 12/22:24 pmKIN - ORD
1 stop19h 53mSpirit Airlines
Deal found 10/9$363
This Mytrip deal was found by Cheapflights users on 10/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:58 pmORD - MBJ
2 stops16h 02mSpirit Airlines
Wed 10/2912:09 pmMBJ - ORD
2 stops22h 04mSpirit Airlines
Deal found 10/9$365

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 October 10, 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

Wed 10/29

6:02 am-1:29 pm

1 stop7h 27m

Montego Bay Sangster Intl

Wed 11/5

2:48 pm-6:13 pm

Nonstop4h 25m

$361

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Tue 1/13

7:30 am-3:15 pm

1 stop6h 45m

Montego Bay Sangster Intl

Fri 1/23

2:10 pm-8:39 pm

1 stop7h 29m

$371

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Tue 1/13

6:40 pm-2:37 pm

2 stops18h 57m

Montego Bay Sangster Intl

Fri 1/23

3:55 pm-11:59 pm

1 stop9h 04m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 2/2

6:10 pm-12:47 pm

1 stop17h 37m

Montego Bay Sangster Intl

Fri 2/6

2:10 pm-8:38 pm

1 stop7h 28m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 1/7

7:10 am-3:15 pm

1 stop7h 05m

Montego Bay Sangster Intl

Wed 1/14

4:40 pm-11:54 pm

1 stop8h 14m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 2/1

5:55 pm-11:10 am

1 stop16h 15m

Montego Bay Sangster Intl

Fri 2/6

12:35 pm-9:14 pm

1 stop9h 39m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 2/1

7:55 pm-11:10 am

1 stop14h 15m

Montego Bay Sangster Intl

Thu 2/5

12:35 pm-9:14 pm

1 stop9h 39m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 1/7

6:00 am-12:40 pm

1 stop5h 40m

Montego Bay Sangster Intl

Tue 1/13

4:05 pm-8:54 am

1 stop17h 49m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 1/7

6:00 am-12:40 pm

1 stop5h 40m

Montego Bay Sangster Intl

Thu 1/15

4:05 pm-8:54 am

1 stop17h 49m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 2/18

11:19 am-8:25 pm

1 stop8h 06m

Montego Bay Sangster Intl

Wed 2/25

8:00 am-4:37 pm

2 stops9h 37m

$376

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/7

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, 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 $419). 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 October 10, 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 57% 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 October 10, 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 United Airlines, Delta, and Spirit Airlines fly from Illinois to Jamaica in about 5h 51m. The time it takes to get you to your destination can typically vary by up to 1h 36m. There are 1785 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 United Airlines, which is currently one of the cheapest options available, starting at $157. Delta flights start at $162 while deals on Southwest start at $162 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 $419). 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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Fort Lauderdale to Luis Munoz Marin Intl flights
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Minneapolis to Luis Munoz Marin Intl flights
LaGuardia to Santiago de los Caballeros flights
Miami to Punta Cana flights
Newark to Nassau flights
Newark to Saint Thomas Island flights
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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 October 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$266Average$442FlexibilityNo cancel feeOn-time65%
FrontierCheapest$333Average$657FlexibilityNo cancel feeOn-time62%
DeltaCheapest$369Average$742FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$383Average$633FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$441Average$675FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$549Average$723FlexibilityNo cancel feeOn-time63%

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