HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Illinois

$149+ Cheap flights from Jamaica to Illinois

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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — ORD
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Jamaica to Illinois with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Jamaica to Illinois

Keep the following information in mind while searching for Jamaica to Illinois flight deals. Data was last updated August 1, 2025.

Round-trip from

$270
(Priceline)

One-way from

$149
(FlightHub)

Popular in

January

Cheapest in

September

Average price

$464

Good round-trip deal

$410 or less

Good one-way deal

$209 or less
From Jamaica to Illinois
Search Deals
One-way flight from Jamaica to Illinois
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals
Price to beat on a round-trip flight from Jamaica to Illinois.
Search Deals
Price to beat on a one-way flight from Jamaica to Illinois.
Search Deals

Find flight deals from Jamaica to Illinois

Cheapest flights from Jamaica to Illinois
Explore the most affordable flight options available from Jamaica to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2025.

This Priceline deal was found by Cheapflights users on 8/1. 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.
Sat 9/2012:10 pmMBJ - ORD
1 stop10h 38mSpirit Airlines
Tue 9/235:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Deal found 8/1$270
This Delta deal was found by Cheapflights users on 7/29. 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.
Thu 10/22:35 pmMBJ - MDW
1 stop7h 01mDelta
Mon 10/66:00 amMDW - MBJ
1 stop9h 34mDelta
Deal found 7/29$339
This Mytrip deal was found by Cheapflights users on 7/31. 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.
Thu 8/1410:22 amMBJ - ORD
1 stop8h 45mMultiple Airlines
Thu 8/216:00 pmORD - MBJ
1 stop13h 55mMultiple Airlines
Deal found 7/31$348
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/212:50 pmMBJ - MDW
2 stops7h 50mSouthwest
Mon 10/65:00 amMDW - MBJ
1 stop8h 55mSouthwest
Deal found 7/29$348
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/2012:08 pmKIN - ORD
1 stop10h 40mSpirit Airlines
Sat 9/276:44 pmORD - KIN
1 stop16h 18mSpirit Airlines
Deal found 7/31$351
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/142:12 pmMBJ - MDW
1 stop9h 08mFrontier
Sun 9/216:20 amMDW - MBJ
1 stop6h 21mFrontier
Deal found 7/31$352
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/79:10 amMBJ - ORD
1 stop15h 12mFrontier
Tue 8/125:38 pmORD - MBJ
1 stop14h 17mFrontier
Deal found 7/30$359
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Thu 8/282:00 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Fri 8/2910:10 pmORD - MBJ
1 stop16h 24mAmerican Airlines
Deal found 7/30$363
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 9/131:00 pmKIN - ORD
2 stops10h 48mAmerican Airlines
Sat 9/208:37 amORD - KIN
2 stops11h 01mAmerican Airlines
Deal found 7/30$416
This Priceline deal was found by Cheapflights users on 7/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/122:20 amKIN - ORD
1 stop14h 01mJetBlue
Sat 9/208:34 amORD - KIN
1 stop16h 36mJetBlue
Deal found 7/30$489
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/79:10 amMBJ - MDW
1 stop14h 07mMultiple Airlines
Mon 8/116:20 amMDW - MBJ
2 stops28h 45mMultiple Airlines
Deal found 7/30$550
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Sat 9/1312:08 pmKIN - ORD
3 stops26h 07mMultiple Airlines
Sat 9/206:30 amORD - KIN
3 stops28h 32mMultiple Airlines
Deal found 7/30$563

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jamaica to Illinois 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 August 1, 2025.
Use the filters below to find and compare flights from Jamaica to Illinois that are best for you.

Fly from

Jamaica

Fly to

Illinois

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 9/20

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Tue 9/23

5:05 am-11:05 am

1 stop6h 00m

$270

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 10/2

2:35 pm-9:36 pm

1 stop7h 01m

Chicago Midway

Mon 10/6

6:00 am-3:34 pm

1 stop9h 34m

$339

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 8/14

10:22 am-7:07 pm

1 stop8h 45m

Chicago O'Hare Intl

Thu 8/21

6:00 pm-7:55 am

1 stop13h 55m

$348

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 10/2

12:50 pm-8:40 pm

2 stops7h 50m

Chicago Midway

Mon 10/6

5:00 am-1:55 pm

1 stop8h 55m

$348

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 9/20

12:08 pm-10:48 pm

1 stop10h 40m

Chicago O'Hare Intl

Sat 9/27

6:44 pm-11:02 am

1 stop16h 18m

$351

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 9/14

2:12 pm-11:20 pm

1 stop9h 08m

Chicago Midway

Sun 9/21

6:20 am-12:41 pm

1 stop6h 21m

$352

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sun 9/14

2:12 pm-12:10 am

1 stop9h 58m

Chicago O'Hare Intl

Sun 9/21

5:10 am-12:41 pm

1 stop7h 31m

$362

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 8/28

2:00 pm-6:30 pm

Nonstop4h 30m

Chicago O'Hare Intl

Fri 8/29

10:10 pm-2:34 pm

1 stop16h 24m

$363

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 9/13

1:00 pm-11:48 pm

2 stops10h 48m

Chicago O'Hare Intl

Sat 9/20

8:37 am-7:38 pm

2 stops11h 01m

$416

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 9/12

2:20 am-4:21 pm

1 stop14h 01m

Chicago O'Hare Intl

Sat 9/20

8:34 am-1:10 am

1 stop16h 36m

$489

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 26 results
1
2
3

Best time to book a flight from Jamaica to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Jamaica 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 Jamaica to Illinois

What is the cheapest month to book a flight from Jamaica to Illinois?

Currently, August is the cheapest month in which you can book a flight from Jamaica to Illinois (average of $245). Flying from Jamaica to Illinois in March is currently the most expensive (average of $321). 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 JM to IL?

Find hourly flight availability from Jamaica to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 1, 2025.

When flying from Jamaica to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated August 1, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Jamaica to Illinois. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,983 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,904 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,915 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Jamaica to Illinois. 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 Jamaica to Illinois one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $149. However, be on the lookout for offers from United Airlines and Delta, as they are both options that can get you from Jamaica to Illinois for a low price.

  • Can I find deals for flights from Jamaica to Illinois that include hotel bookings?

    Yes. In addition to deals on Jamaica to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Jamaica to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Jamaica to Illinois.

  • Can I find deals for business class flights from Jamaica to Illinois?

    Yes. Cheapflights offers flight deals from Jamaica to Illinois 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 Jamaica to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Jamaica to Illinois (average of $245). Flying from Jamaica to Illinois in March is currently the most expensive (average of $321). 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 Jamaica to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
Luis Munoz Marin Intl to Orlando flights
Luis Munoz Marin Intl to John F Kennedy Intl flights
Luis Munoz Marin Intl to Newark flights
Santo Domingo to John F Kennedy Intl flights
Santo Domingo to Newark flights
Luis Munoz Marin Intl to LaGuardia flights
Santiago de los Caballeros to John F Kennedy Intl flights
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Fort Lauderdale flights
Luis Munoz Marin Intl to Tampa flights
Luis Munoz Marin Intl to Miami flights
Aguadilla to Orlando flights
Santiago de los Caballeros to Newark flights
Port of Spain to John F Kennedy Intl flights
Luis Munoz Marin Intl to Philadelphia flights
Luis Munoz Marin Intl to Midway flights
Santo Domingo to LaGuardia flights
Santo Domingo to Boston flights
Luis Munoz Marin Intl to Boston flights
Ponce to Orlando flights
Luis Munoz Marin Intl to Dallas/Fort Worth flights
Luis Munoz Marin Intl to Atlanta flights
Santo Domingo to Orlando flights
Nassau to Fort Lauderdale flights
Port of Spain to Miami flights
Luis Munoz Marin Intl to Hartford flights
Luis Munoz Marin Intl to Hobby flights
Santo Domingo to Miami flights
Kingston to John F Kennedy Intl flights
Luis Munoz Marin Intl to Reagan-National flights
Nassau to Orlando flights
Luis Munoz Marin Intl to Las Vegas flights
Montego Bay to John F Kennedy Intl flights
Luis Munoz Marin Intl to Denver flights
Luis Munoz Marin Intl to Baltimore flights
Kingston to Fort Lauderdale flights
Luis Munoz Marin Intl to George Bush Intcntl flights
Santo Domingo to Fort Lauderdale flights
Nassau to Miami flights
Bridgetown to John F Kennedy Intl flights
Luis Munoz Marin Intl to Dulles Intl flights
Punta Cana to John F Kennedy Intl flights
Luis Munoz Marin Intl to Austin flights
Luis Munoz Marin Intl to Charlotte flights
Luis Munoz Marin Intl to Seattle flights
Santiago de los Caballeros to LaGuardia flights
Luis Munoz Marin Intl to Los Angeles flights
Luis Munoz Marin Intl to Raleigh flights
Luis Munoz Marin Intl to Milwaukee flights
Port of Spain to Newark flights

Top 5 airlines flying from Jamaica to Illinois

Discover the top 5 airlines that operate flights from Jamaica to Illinois. 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 August 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$360FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$255Average$480FlexibilityNo cancel feeOn-time69%
DeltaCheapest$322Average$411FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$392Average$550FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$392Average$529FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.