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Jamaica

$109+ 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
jul. 7 — jul. 141
lun. 7/7
lun. 7/14
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 julio 2, 2025.

Round-trip from

$341
(FlightHub)

One-way from

$109
(Priceline)

Popular in

March

Cheapest in

January

Average price

$613

Good round-trip deal

$526 or less

Good one-way deal

$247 or less
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. 1% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 2, 2025.

This FlightHub deal was found by Cheapflights users on 7/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 7/275:05 amORD - KIN
1 stop5h 55mSpirit Airlines
sáb. 8/28:47 amKIN - ORD
1 stop15h 06mSpirit Airlines
Deal found 7/1$341
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
jue. 8/1410:37 amSTL - MBJ
1 stop24h 37mSpirit Airlines
jue. 8/2112:19 pmMBJ - STL
2 stops25h 13mSpirit Airlines
Deal found 7/1$377
This Delta deal was found by Cheapflights users on 6/30. 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.
dom. 9/76:00 amSTL - MBJ
1 stop9h 38mDelta
vie. 9/122:35 pmMBJ - STL
1 stop8h 49mDelta
Deal found 6/30$383
This American Airlines deal was found by Cheapflights users on 7/2. 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.
vie. 10/37:15 pmORD - KIN
1 stop16h 37mAmerican Airlines
vie. 10/317:00 amKIN - ORD
1 stop16h 47mAmerican Airlines
Deal found 7/2$391
This Delta deal was found by Cheapflights users on 6/30. 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.
vie. 8/156:04 amMDW - KIN
1 stop14h 21mDelta
vie. 8/229:25 amKIN - MDW
1 stop12h 19mDelta
Deal found 6/30$393
This Mytrip deal was found by Cheapflights users on 7/1. 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.
vie. 8/1511:21 amORD - KIN
2 stops24h 06mMultiple Airlines
vie. 8/226:25 pmKIN - ORD
2 stops15h 27mMultiple Airlines
Deal found 7/1$399
This American Airlines deal was found by Cheapflights users on 7/1. 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.
vie. 10/35:00 amORD - MBJ
1 stop9h 54mAmerican Airlines
jue. 10/92:00 pmMBJ - ORD
Nonstop4h 33mAmerican Airlines
Deal found 7/1$400
This CheapOair deal was found by Cheapflights users on 7/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/115:05 amORD - MBJ
1 stop6h 00mMultiple Airlines
lun. 8/189:05 amMBJ - ORD
1 stop15h 17mMultiple Airlines
Deal found 7/2$401
This Priceline deal was found by Cheapflights users on 7/1. 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.
sáb. 9/206:10 amMDW - MBJ
1 stop6h 35mFrontier
sáb. 9/272:05 pmMBJ - MDW
1 stop8h 28mFrontier
Deal found 7/1$401
This FlightHub deal was found by Cheapflights users on 7/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/175:05 amORD - MBJ
1 stop6h 05mSpirit Airlines
dom. 9/2112:15 pmMBJ - ORD
1 stop10h 33mSpirit Airlines
Deal found 7/2$402
This Delta deal was found by Cheapflights users on 7/1. 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.
sáb. 8/237:05 amORD - KIN
1 stop13h 20mDelta
sáb. 8/309:25 amKIN - ORD
1 stop9h 54mDelta
Deal found 7/1$403
This Delta deal was found by Cheapflights users on 6/29. 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.
sáb. 10/186:10 pmORD - MBJ
1 stop17h 28mDelta
mié. 10/222:19 pmMBJ - ORD
1 stop9h 34mDelta
Deal found 6/29$410

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 julio 2, 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

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

dom. 7/27

5:05 am-11:00 am

1 stop5h 55m

Kingston Norman Manley

sáb. 8/2

8:47 am-11:53 pm

1 stop15h 06m

$341

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

jue. 8/14

10:37 am-11:14 am

1 stop24h 37m

Montego Bay Sangster Intl

jue. 8/21

12:19 pm-1:32 pm

2 stops25h 13m

$377

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

dom. 9/7

7:00 am-3:38 pm

1 stop8h 38m

Montego Bay Sangster Intl

vie. 9/12

4:59 pm-11:24 pm

1 stop6h 25m

$383

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

vie. 10/3

7:15 pm-11:52 am

1 stop16h 37m

Kingston Norman Manley

vie. 10/31

7:00 am-11:47 pm

1 stop16h 47m

$391

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

vie. 8/15

6:04 am-8:25 pm

1 stop14h 21m

Kingston Norman Manley

vie. 8/22

9:25 am-9:44 pm

1 stop12h 19m

$393

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

vie. 8/15

11:21 am-11:27 am

2 stops24h 06m

Kingston Norman Manley

vie. 8/22

6:25 pm-9:52 am

2 stops15h 27m

$399

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mar. 7/15

7:05 am-3:25 pm

1 stop8h 20m

Montego Bay Sangster Intl

sáb. 7/26

2:26 pm-7:00 pm

Nonstop4h 34m

$400

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

sáb. 9/20

6:10 am-12:45 pm

1 stop6h 35m

Montego Bay Sangster Intl

sáb. 9/27

2:05 pm-10:33 pm

1 stop8h 28m

$401

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

lun. 8/11

5:05 am-11:05 am

1 stop6h 00m

Montego Bay Sangster Intl

lun. 8/18

9:05 am-12:22 am

1 stop15h 17m

$401

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mié. 9/17

5:05 am-11:10 am

1 stop6h 05m

Montego Bay Sangster Intl

dom. 9/21

12:15 pm-10:48 pm

1 stop10h 33m

$402

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 52 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 $403). Flying from Illinois to Jamaica in July is currently the most expensive (average of $569). 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 julio 2, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Jamaica as you normally would.

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated julio 2, 2025.
Read through reviews of airlines operating flights from Illinois to Jamaica, such as Southwest, Delta, and Copa Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,272 reviews

Food

7.0

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.0

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,983 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.0

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Copa Airlines
7.5
Good
1,465 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.0

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,861 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.0

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,918 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.0

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • 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 $109. Spirit Airlines flights start at $113 while deals on American Airlines start at $164 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 $403). Flying from Illinois to Jamaica in July is currently the most expensive (average of $569). 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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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 julio 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$276Average$437FlexibilityNo cancel feeOn-time65%
DeltaCheapest$295Average$813FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$338Average$436FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$412Average$622FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$432Average$687FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$555Average$726FlexibilityNo cancel feeOn-time63%

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