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Jamaica

$111+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$346
(Booking.com)

One-way from

$111
(Cheapflightsfares)

Popular in

December

Cheapest in

February

Average price

$666

Good round-trip deal

$514 or less

Good one-way deal

$240 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 ($20 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 March 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 March 31, 2025.

This Booking.com deal was found by Cheapflights users on 3/30. 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 Booking.com 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 3/30$346
This Mytrip deal was found by Cheapflights users on 3/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1110:10 amSTL - MBJ
1 stop24h 52mSpirit Airlines
Fri 5/1612:07 pmMBJ - STL
1 stop21h 08mSpirit Airlines
Deal found 3/29$400
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/75:45 pmSTL - MBJ
2 stops17h 17mMultiple Airlines
Sat 5/1012:07 pmMBJ - STL
1 stop21h 08mMultiple Airlines
Deal found 3/29$403
This American Airlines deal was found by Cheapflights users on 3/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/75:13 amSTL - MBJ
1 stop8h 23mAmerican Airlines
Sat 5/103:40 pmMBJ - STL
1 stop6h 39mAmerican Airlines
Deal found 3/29$421
This American Airlines deal was found by Cheapflights users on 3/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/147:00 amORD - KIN
2 stops12h 40mAmerican Airlines
Wed 5/216:30 amKIN - ORD
2 stops10h 59mAmerican Airlines
Deal found 3/30$437
This Delta deal was found by Cheapflights users on 3/29. 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.
Mon 4/2812:48 pmMDW - KIN
1 stop7h 12mDelta
Mon 5/59:00 amKIN - MDW
1 stop8h 59mDelta
Deal found 3/29$443
This Delta deal was found by Cheapflights users on 3/30. 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.
Wed 5/149:39 amORD - KIN
1 stop10h 21mDelta
Wed 5/219:00 amKIN - ORD
1 stop8h 11mDelta
Deal found 3/30$443
This Delta deal was found by Cheapflights users on 3/30. 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.
Tue 7/87:20 amSTL - MBJ
1 stop5h 37mDelta
Wed 7/165:01 pmMBJ - STL
1 stop6h 38mDelta
Deal found 3/30$457
This Booking.com deal was found by Cheapflights users on 3/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/246:15 pmORD - KIN
2 stops42h 20mMultiple Airlines
Sat 5/311:34 pmKIN - ORD
1 stop10h 31mMultiple Airlines
Deal found 3/30$461
This Mytrip deal was found by Cheapflights users on 3/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/277:47 amORD - MBJ
2 stops27h 15mMultiple Airlines
Sat 5/313:05 pmMBJ - ORD
1 stop9h 00mMultiple Airlines
Deal found 3/30$462
This Delta deal was found by Cheapflights users on 3/30. 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.
Wed 9/36:00 amMDW - MBJ
1 stop9h 36mDelta
Wed 9/101:12 pmMBJ - MDW
1 stop8h 32mDelta
Deal found 3/30$463
This Delta deal was found by Cheapflights users on 3/30. 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.
Sun 9/217:10 amORD - MBJ
1 stop8h 23mDelta
Wed 10/11:12 pmMBJ - ORD
1 stop8h 00mDelta
Deal found 3/30$463

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 March 31, 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

Wed 5/21

1:34 pm-11:04 pm

1 stop9h 30m

$346

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Sun 5/11

10:10 am-11:02 am

1 stop24h 52m

Montego Bay Sangster Intl

Fri 5/16

12:07 pm-9:15 am

1 stop21h 08m

$400

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Wed 5/7

5:45 pm-11:02 am

2 stops17h 17m

Montego Bay Sangster Intl

Sat 5/10

12:07 pm-9:15 am

1 stop21h 08m

$403

St. LouisMontego Bay

STL - MBJ

STLMBJ

Lambert-St Louis

Wed 5/7

5:13 am-1:36 pm

1 stop8h 23m

Montego Bay Sangster Intl

Sat 5/10

3:40 pm-10:19 pm

1 stop6h 39m

$421

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 5/14

7:00 am-7:40 pm

2 stops12h 40m

Kingston Norman Manley

Wed 5/21

6:30 am-5:29 pm

2 stops10h 59m

$437

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 4/28

12:48 pm-8:00 pm

1 stop7h 12m

Kingston Norman Manley

Mon 5/5

9:00 am-5:59 pm

1 stop8h 59m

$443

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 5/14

9:39 am-8:00 pm

1 stop10h 21m

Kingston Norman Manley

Wed 5/21

9:00 am-5:11 pm

1 stop8h 11m

$443

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 5/24

6:15 pm-12:35 pm

2 stops42h 20m

Kingston Norman Manley

Sat 5/31

1:34 pm-12:05 am

1 stop10h 31m

$461

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 5/27

7:47 am-11:02 am

2 stops27h 15m

Montego Bay Sangster Intl

Sat 5/31

3:05 pm-12:05 am

1 stop9h 00m

$462

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 9/3

6:00 am-3:36 pm

1 stop9h 36m

Montego Bay Sangster Intl

Wed 9/10

1:12 pm-9:44 pm

1 stop8h 32m

$463

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 55 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 March 31, 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 March 31, 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 March 31, 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
4,275 reviews

Boarding

8.2

Crew

8.7

Food

7.1

Overall

8.0

Comfort

8.1

Entertainment

7.6

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
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Boarding

8.2

Crew

8.7

Food

7.1

Overall

8.0

Comfort

8.1

Entertainment

7.6

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
7,899 reviews
Southwest
8.0
Very good
4,275 reviews

Boarding

8.2

Crew

8.7

Food

7.1

Overall

8.0

Comfort

8.1

Entertainment

7.6

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
1,400 reviews
Southwest
8.0
Very good
4,275 reviews

Boarding

8.2

Crew

8.7

Food

7.1

Overall

8.0

Comfort

8.1

Entertainment

7.6

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.
SWISS
7.5
Good
1,570 reviews
Southwest
8.0
Very good
4,275 reviews

Boarding

8.2

Crew

8.7

Food

7.1

Overall

8.0

Comfort

8.1

Entertainment

7.6

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
8,614 reviews
Southwest
8.0
Very good
4,275 reviews

Boarding

8.2

Crew

8.7

Food

7.1

Overall

8.0

Comfort

8.1

Entertainment

7.6

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 $111. Delta flights start at $183 while deals on Frontier start at $191 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

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.
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
LaGuardia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santo Domingo flights
John F Kennedy Intl to Montego Bay flights
Orlando to Luis Munoz Marin Intl flights
Newark to Punta Cana flights
Boston to Luis Munoz Marin Intl flights
Newark to Santiago de los Caballeros flights
Newark to Santo Domingo flights
Newark to Oranjestad flights
Newark to Montego Bay flights
O'Hare Intl to Luis Munoz Marin Intl flights
Dulles Intl to Luis Munoz Marin Intl flights
Philadelphia to Luis Munoz Marin Intl flights
Reagan-National to Luis Munoz Marin Intl flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Newark to Nassau flights
Atlanta to Luis Munoz Marin Intl flights
John F Kennedy Intl to Oranjestad flights
Hartford to Luis Munoz Marin Intl flights
Baltimore to Luis Munoz Marin Intl flights
Tampa to Luis Munoz Marin Intl flights
Miami to Luis Munoz Marin Intl flights
LaGuardia to Punta Cana flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Newark to Simpson Bay flights
Boston to Oranjestad flights
John F Kennedy Intl to Nassau flights
John F Kennedy Intl to Bridgetown flights
John F Kennedy Intl to Kingston flights
John F Kennedy Intl to Simpson Bay flights
Atlanta to Montego Bay flights
Dulles Intl to Punta Cana flights
LaGuardia to Montego Bay flights
O'Hare Intl to Punta Cana flights
John F Kennedy Intl to Saint Thomas Island flights
Newark to Providenciales flights
John F Kennedy Intl to St. John's flights
Dulles Intl to Montego Bay flights
Boston to Punta Cana flights
Philadelphia to Punta Cana flights
LaGuardia to Oranjestad flights
Atlanta to Punta Cana flights
Raleigh to Luis Munoz Marin Intl flights
Newark to Saint Thomas Island flights
John F Kennedy Intl to Providenciales flights
Hobby to Luis Munoz Marin Intl 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 March 31, 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$691FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$393Average$610FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$579Average$735FlexibilityNo cancel feeOn-time63%
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