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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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$284
(Cheapflightsfares)

One-way from

$114
(Cheapflightsfares)

Popular in

March

Cheapest in

February

Average price

$538

Good round-trip deal

$532 or less

Good one-way deal

$252 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. 0% potential increase in price ($3 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/145:05 amORD - KIN
1 stop7h 24mSpirit Airlines
Wed 5/211:34 pmKIN - ORD
1 stop9h 30mSpirit Airlines
Deal found 4/17$284
This Mytrip deal was found by Cheapflights users on 4/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1710:10 amSTL - MBJ
1 stop24h 52mSpirit Airlines
Sat 5/2412:07 pmMBJ - STL
1 stop21h 08mSpirit Airlines
Deal found 4/16$339
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Sat 5/173:16 pmORD - KIN
2 stops21h 13mMultiple Airlines
Wed 5/211:34 pmKIN - ORD
1 stop9h 30mMultiple Airlines
Deal found 4/17$400
This American Airlines deal was found by Cheapflights users on 4/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/306:33 pmSTL - MBJ
2 stops14h 42mAmerican Airlines
Sat 9/61:05 pmMBJ - STL
2 stops10h 44mAmerican Airlines
Deal found 4/16$436
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Sat 5/175:45 pmSTL - MBJ
2 stops17h 17mMultiple Airlines
Sat 5/243:05 pmMBJ - STL
1 stop18h 10mMultiple Airlines
Deal found 4/16$437
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/36:00 amSTL - MBJ
1 stop9h 30mDelta
Wed 6/44:55 pmMBJ - STL
1 stop6h 43mDelta
Deal found 4/16$457
This Mytrip deal was found by Cheapflights users on 4/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/65:20 pmORD - MBJ
3 stops41h 42mSpirit Airlines
Wed 6/1112:07 pmMBJ - ORD
1 stop10h 57mSpirit Airlines
Deal found 4/17$458
This United Airlines deal was found by Cheapflights users on 4/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/296:00 amORD - MBJ
1 stop7h 10mUnited Airlines
Sat 5/31:51 pmMBJ - ORD
Nonstop4h 29mUnited Airlines
Deal found 4/17$460
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/66:20 amMDW - MBJ
1 stop7h 35mSouthwest
Sat 5/101:50 pmMBJ - MDW
Nonstop4h 15mSouthwest
Deal found 4/16$460
This American Airlines deal was found by Cheapflights users on 4/17. 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 9/305:15 amORD - MBJ
1 stop5h 55mAmerican Airlines
Fri 10/31:05 pmMBJ - ORD
2 stops10h 52mAmerican Airlines
Deal found 4/17$461
This CheapOair deal was found by Cheapflights users on 4/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/118:30 amMDW - MBJ
1 stop28h 12mFrontier
Fri 5/162:07 pmMBJ - MDW
1 stop19h 26mFrontier
Deal found 4/16$463
This CheapOair deal was found by Cheapflights users on 4/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/57:47 pmORD - MBJ
1 stop15h 08mMultiple Airlines
Mon 5/122:08 pmMBJ - ORD
1 stop9h 03mMultiple Airlines
Deal found 4/17$464

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 April 17, 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

Wed 5/14

5:05 am-12:29 pm

1 stop7h 24m

Kingston Norman Manley

Mon 5/19

1:34 pm-12:05 am

1 stop10h 31m

$334

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Sat 5/17

10:10 am-11:02 am

1 stop24h 52m

Montego Bay Sangster Intl

Sat 5/24

12:07 pm-9:15 am

1 stop21h 08m

$339

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 5/15

5:31 pm-12:29 pm

2 stops18h 58m

Kingston Norman Manley

Tue 5/20

1:34 pm-11:04 pm

1 stop9h 30m

$407

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Sat 5/17

5:45 pm-11:02 am

2 stops17h 17m

Montego Bay Sangster Intl

Sat 5/24

3:05 pm-9:15 am

1 stop18h 10m

$437

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Tue 6/3

6:00 am-3:30 pm

1 stop9h 30m

Montego Bay Sangster Intl

Wed 6/4

4:55 pm-11:38 pm

1 stop6h 43m

$457

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 6/6

5:20 pm-11:02 am

3 stops41h 42m

Montego Bay Sangster Intl

Wed 6/11

12:07 pm-11:04 pm

1 stop10h 57m

$458

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 4/29

6:00 am-1:10 pm

1 stop7h 10m

Montego Bay Sangster Intl

Sat 5/3

1:51 pm-6:20 pm

Nonstop4h 29m

$460

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 5/6

6:20 am-1:55 pm

1 stop7h 35m

Montego Bay Sangster Intl

Sat 5/10

1:50 pm-6:05 pm

Nonstop4h 15m

$460

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Sat 7/12

4:07 pm-9:30 am

2 stops17h 23m

Montego Bay Sangster Intl

Thu 7/17

4:25 pm-8:14 am

1 stop15h 49m

$461

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 5/11

8:30 am-12:42 pm

1 stop28h 12m

Montego Bay Sangster Intl

Fri 5/16

2:07 pm-9:33 am

1 stop19h 26m

$463

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 54 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 April 17, 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 April 17, 2025.

The most flights from USIL to JM0 are scheduled on a Monday (2 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 April 17, 2025.
See what other customers who have flown with Southwest, Delta and Copa Airlines 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
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Copa Airlines
7.6
Good
1,409 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,667 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,926 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $114. Copa Airlines flights start at $183 while deals on Delta start at $187 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.
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santiago de los Caballeros flights
John F Kennedy Intl to Punta Cana flights
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LaGuardia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Montego Bay flights
Newark to Punta Cana flights
Philadelphia to Luis Munoz Marin Intl flights
Newark to Santiago de los Caballeros flights
John F Kennedy Intl to Santo Domingo flights
Dulles Intl to Luis Munoz Marin Intl flights
Newark to Montego Bay flights
Boston to Luis Munoz Marin Intl flights
Baltimore to Luis Munoz Marin Intl flights
John F Kennedy Intl to Oranjestad flights
Newark to Santo Domingo flights
Reagan-National to Luis Munoz Marin Intl flights
Newark to Oranjestad flights
O'Hare Intl to Luis Munoz Marin Intl flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Tampa to Luis Munoz Marin Intl flights
Hartford to Luis Munoz Marin Intl flights
Atlanta to Luis Munoz Marin Intl flights
Miami to Luis Munoz Marin Intl flights
Atlanta to Montego Bay flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Newark to Nassau flights
Hobby to Luis Munoz Marin Intl flights
LaGuardia to Punta Cana flights
John F Kennedy Intl to Nassau flights
John F Kennedy Intl to Kingston flights
John F Kennedy Intl to Simpson Bay flights
John F Kennedy Intl to Bridgetown flights
Boston to Oranjestad flights
Atlanta to Punta Cana flights
LaGuardia to Montego Bay flights
Dulles Intl to Punta Cana flights
John F Kennedy Intl to Saint Thomas Island flights
George Bush Intcntl to Luis Munoz Marin Intl flights
Raleigh to Luis Munoz Marin Intl flights
Newark to Simpson Bay flights
O'Hare Intl to Punta Cana flights
Dulles Intl to Montego Bay flights
Newark to Providenciales flights
John F Kennedy Intl to St. John's flights
Boston to Punta Cana flights
John F Kennedy Intl to Port of Spain flights
LaGuardia to Oranjestad flights
Dallas/Fort Worth to Punta Cana 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$205Average$265FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$273Average$440FlexibilityNo cancel feeOn-time65%
DeltaCheapest$295Average$679FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$393Average$695FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$394Average$618FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$579Average$748FlexibilityNo cancel feeOn-time63%

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