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$118+ 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
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 February 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$303
(FlightHub)

One-way from

$118
(Cheapflightsfares)

Popular in

December

Cheapest in

May

Average price

$484

Good round-trip deal

$537 or less

Good one-way deal

$242 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. 7% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 23, 2025.

This FlightHub deal was found by Cheapflights users on 2/22. 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.
Tue 3/256:25 pmORD - KIN
2 stops18h 03mSpirit Airlines
Tue 4/11:36 pmKIN - ORD
2 stops19h 08mSpirit Airlines
Deal found 2/22$303
This FlightHub deal was found by Cheapflights users on 2/22. 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.
Thu 4/36:47 pmSTL - KIN
1 stop17h 41mSpirit Airlines
Mon 4/141:39 pmKIN - STL
1 stop27h 37mSpirit Airlines
Deal found 2/22$350
This Delta deal was found by Cheapflights users on 2/22. 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.
Tue 3/2511:20 amORD - KIN
1 stop8h 40mDelta
Tue 4/19:00 amKIN - ORD
1 stop7h 20mDelta
Deal found 2/22$369
This Delta deal was found by Cheapflights users on 2/22. 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.
Fri 3/712:44 pmMDW - KIN
1 stop6h 16mDelta
Tue 3/119:00 amKIN - MDW
1 stop7h 14mDelta
Deal found 2/22$379
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 3/245:24 pmSTL - MBJ
2 stops17h 38mMultiple Airlines
Wed 4/212:07 pmMBJ - STL
1 stop29h 45mMultiple Airlines
Deal found 2/22$395
This Cheapflightsfares deal was found by Cheapflights users on 2/22. 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.
Thu 5/297:37 pmSTL - MBJ
1 stop13h 37mSpirit Airlines
Tue 6/310:19 amMBJ - STL
1 stop8h 13mSpirit Airlines
Deal found 2/22$398
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Sat 3/18:25 amSTL - MBJ
1 stop6h 51mUnited Airlines
Sat 3/85:18 pmMBJ - STL
1 stop16h 50mUnited Airlines
Deal found 2/21$421
This American Airlines deal was found by Cheapflights users on 2/22. 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.
Fri 3/71:54 pmORD - KIN
1 stop5h 36mAmerican Airlines
Sun 3/95:00 amKIN - ORD
1 stop19h 20mAmerican Airlines
Deal found 2/22$427
This American Airlines deal was found by Cheapflights users on 2/22. 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.
Wed 3/55:37 pmSTL - MBJ
1 stop20h 38mAmerican Airlines
Sun 3/910:15 amMBJ - STL
2 stops12h 03mAmerican Airlines
Deal found 2/22$437
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 3/67:57 amORD - KIN
2 stops14h 58mMultiple Airlines
Mon 3/101:36 pmKIN - ORD
1 stop19h 31mMultiple Airlines
Deal found 2/22$439
This FlightHub deal was found by Cheapflights users on 2/21. 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.
Sat 3/227:45 pmORD - MBJ
2 stops15h 17mSpirit Airlines
Thu 3/2712:07 pmMBJ - ORD
2 stops20h 37mSpirit Airlines
Deal found 2/21$441
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 3/276:47 pmSTL - KIN
1 stop17h 41mMultiple Airlines
Sun 4/67:05 amKIN - STL
1 stop10h 47mMultiple Airlines
Deal found 2/22$444

Find flights from Illinois to Jamaica within your budget

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 February 23, 2025.

Fly from

Illinois

Fly to

Jamaica

Route

Depart

Return

Price

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 3/25

6:25 pm-12:28 pm

2 stops18h 03m

Kingston Norman Manley

Tue 4/1

1:36 pm-8:44 am

2 stops19h 08m

$303

St. LouisKingston

STL - KIN

STLKIN

Lambert-St Louis

Thu 4/3

6:47 pm-12:28 pm

1 stop17h 41m

Kingston Norman Manley

Mon 4/14

1:39 pm-5:16 pm

1 stop27h 37m

$350

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 3/25

11:20 am-8:00 pm

1 stop8h 40m

Kingston Norman Manley

Tue 4/1

9:00 am-4:20 pm

1 stop7h 20m

$369

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 3/7

12:44 pm-8:00 pm

1 stop6h 16m

Kingston Norman Manley

Tue 3/11

9:00 am-4:14 pm

1 stop7h 14m

$379

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Mon 3/24

5:24 pm-11:02 am

2 stops17h 38m

Montego Bay Sangster Intl

Wed 4/2

12:07 pm-5:52 pm

1 stop29h 45m

$395

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Sat 3/1

6:30 am-4:16 pm

2 stops8h 46m

Montego Bay Sangster Intl

Sat 3/8

5:18 pm-9:08 am

1 stop16h 50m

$421

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Fri 3/7

1:54 pm-8:30 pm

1 stop5h 36m

Kingston Norman Manley

Sun 3/9

5:00 am-12:20 am

1 stop19h 20m

$427

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Wed 3/5

5:37 pm-3:15 pm

1 stop20h 38m

Montego Bay Sangster Intl

Sun 3/9

10:15 am-10:18 pm

2 stops12h 03m

$437

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 3/6

7:57 am-11:55 pm

2 stops14h 58m

Kingston Norman Manley

Mon 3/10

1:36 pm-9:07 am

1 stop19h 31m

$439

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 3/22

7:45 pm-11:02 am

2 stops15h 17m

Montego Bay Sangster Intl

Thu 3/27

12:07 pm-8:44 am

2 stops20h 37m

$441

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

Showing 1-10 of 48 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.

Travel insights for flights from Illinois to Jamaica

Get recent, data-driven insights about flights from Illinois to Jamaica including ideal travel times, pricing trends, and more.

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 February 23, 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.

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 February 23, 2025.

The most flights from USIL to JM0 are scheduled on a Saturday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Jamaica by month

Plan your trip to Jamaica by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Jamaica ranges from 1.6 - 7.1 inches per month. October is typically the wettest month, when rainfall can reach 7.1 in. February is typically the driest time to visit Jamaica when rainfall is around 1.6 in.

Temperature in Jamaica by month

Plan your trip to Jamaica by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Jamaica, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 February 23, 2025.
See what other customers who have flown with Southwest, Delta and JetBlue from Illinois to Jamaica have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,395 reviews

Crew

8.7

Food

7.1

Overall

8.1

Comfort

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,395 reviews
Southwest
8.1
Very good
4,395 reviews

Crew

8.7

Food

7.1

Overall

8.1

Comfort

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,395 reviews

Crew

8.7

Food

7.1

Overall

8.1

Comfort

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,068 reviews
Southwest
8.1
Very good
4,395 reviews

Crew

8.7

Food

7.1

Overall

8.1

Comfort

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,395 reviews

Crew

8.7

Food

7.1

Overall

8.1

Comfort

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,395 reviews

Crew

8.7

Food

7.1

Overall

8.1

Comfort

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Spirit Airlines, which is currently one of the cheapest options available, starting at $118. Frontier flights start at $136 while deals on Southwest start at $182 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

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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 February 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$205Average$265FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$258Average$429FlexibilityNo cancel feeOn-time65%
DeltaCheapest$368Average$645FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$391Average$589FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$393Average$695FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$576Average$724FlexibilityNo cancel feeOn-time63%
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