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$114+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
dic. 6 — dic. 131
sáb. 12/6
sáb. 12/13
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 noviembre 6, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$346
(Mytrip)

One-way from

$114
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$570

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. 3% potential increase in price ($22 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 noviembre 6, 2025.

This Mytrip deal was found by Cheapflights users on 11/4. 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.
mar. 12/25:00 amORD - KIN
1 stop7h 21mSpirit Airlines
mar. 12/91:19 pmKIN - ORD
1 stop7h 42mSpirit Airlines
Deal found 11/4$346
This Mytrip deal was found by Cheapflights users on 11/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/165:10 amORD - MBJ
1 stop5h 52mSpirit Airlines
sáb. 11/221:07 pmMBJ - ORD
2 stops20h 54mSpirit Airlines
Deal found 11/6$355
This United Airlines deal was found by Cheapflights users on 11/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/298:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
mié. 12/32:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
Deal found 11/6$356
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
dom. 12/73:20 pmORD - KIN
1 stop19h 54mMultiple Airlines
sáb. 12/131:19 pmKIN - ORD
1 stop7h 42mMultiple Airlines
Deal found 11/5$357
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
vie. 12/56:11 amORD - MBJ
1 stop8h 27mFrontier
lun. 12/83:31 pmMBJ - ORD
1 stop24h 41mFrontier
Deal found 11/4$360
This Mytrip deal was found by Cheapflights users on 11/4. 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.
mar. 12/25:00 amORD - KIN
1 stop7h 21mSpirit Airlines
vie. 12/51:19 pmKIN - ORD
1 stop7h 42mSpirit Airlines
Deal found 11/4$362
This Delta deal was found by Cheapflights users on 11/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/276:45 amORD - MBJ
2 stops8h 49mDelta
mié. 12/35:58 pmMBJ - ORD
2 stops15h 06mDelta
Deal found 11/6$363
This Delta deal was found by Cheapflights users on 11/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/276:00 amMDW - MBJ
1 stop7h 11mDelta
mié. 12/35:58 pmMBJ - MDW
1 stop16h 56mDelta
Deal found 11/6$363
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/93:26 pmORD - KIN
1 stop19h 48mSpirit Airlines
vie. 12/121:19 pmKIN - ORD
1 stop11h 50mSpirit Airlines
Deal found 11/6$364
This American Airlines deal was found by Cheapflights users on 11/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/3012:52 amORD - MBJ
1 stop12h 58mAmerican Airlines
dom. 12/72:30 pmMBJ - ORD
Nonstop4h 47mAmerican Airlines
Deal found 11/6$366
This American Airlines deal was found by Cheapflights users on 11/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/298:15 amORD - MBJ
Nonstop3h 59mAmerican Airlines
mié. 12/34:51 pmMBJ - ORD
1 stop7h 48mAmerican Airlines
Deal found 11/6$367
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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.
mar. 12/165:00 amORD - MBJ
1 stop6h 10mSpirit Airlines
mar. 12/231:05 pmMBJ - ORD
1 stop6h 34mSpirit Airlines
Deal found 11/4$368

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 noviembre 6, 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

mar. 12/16

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

mar. 12/23

2:48 pm-6:13 pm

Nonstop4h 25m

$356

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

vie. 1/30

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

mar. 2/10

2:48 pm-6:13 pm

Nonstop4h 25m

$357

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

vie. 11/28

10:15 am-3:28 pm

Nonstop4h 13m

Montego Bay Sangster Intl

mié. 12/3

4:51 pm-9:08 am

1 stop17h 17m

$367

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar. 12/9

6:00 am-2:13 pm

1 stop7h 13m

Montego Bay Sangster Intl

jue. 12/11

2:29 pm-11:47 pm

1 stop10h 18m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar. 12/16

5:05 am-12:50 pm

1 stop6h 45m

Montego Bay Sangster Intl

mar. 12/23

3:55 pm-11:05 pm

1 stop8h 10m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

vie. 1/16

6:45 am-8:36 pm

1 stop12h 51m

Montego Bay Sangster Intl

mar. 1/20

8:00 am-5:32 pm

1 stop10h 32m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

sáb. 1/17

11:21 am-8:36 pm

1 stop8h 15m

Montego Bay Sangster Intl

mié. 1/21

12:38 pm-10:26 pm

1 stop10h 48m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

jue. 12/4

6:00 am-2:13 pm

1 stop7h 13m

Montego Bay Sangster Intl

jue. 12/11

2:29 pm-11:47 pm

1 stop10h 18m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 2/2

6:00 am-3:20 pm

1 stop8h 20m

Montego Bay Sangster Intl

sáb. 2/7

4:45 pm-10:26 pm

1 stop6h 41m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

sáb. 1/24

6:00 am-8:36 pm

1 stop13h 36m

Montego Bay Sangster Intl

jue. 1/29

4:45 pm-10:26 pm

1 stop6h 41m

$371

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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 $260). 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 noviembre 6, 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 noviembre 6, 2025.

The most flights from USIL to JM0 are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 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, American Airlines, and Delta 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 09m. 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 $122. United Airlines flights start at $157 while deals on Southwest start at $157 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 $260). 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

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 noviembre 6, 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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