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$167+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — ORD
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
1 adult, Economy
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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 septiembre 15, 2025.

Round-trip from

$239
(Cheapflightsfares)

One-way from

$167
(Cheapflightsfares)

Popular in

January

Cheapest in

September

Average price

$373

Good round-trip deal

$496 or less

Good one-way deal

$292 or less
From Jamaica to Illinois
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One-way flight from Jamaica to Illinois
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Highest demand for flights based on searches. 13% potential increase in price ($75 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Jamaica to Illinois.
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Price to beat on a one-way flight from Jamaica to Illinois.
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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 septiembre 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
mar. 10/712:09 pmMBJ - ORD
1 stop11h 36mSpirit Airlines
sáb. 10/117:43 pmORD - MBJ
1 stop15h 17mSpirit Airlines
Deal found 9/14$239
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
jue. 10/212:10 pmMBJ - ORD
1 stop10h 38mSpirit Airlines
dom. 10/55:05 amORD - MBJ
1 stop5h 55mSpirit Airlines
Deal found 9/14$249
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
jue. 10/912:14 pmKIN - ORD
1 stop11h 31mSpirit Airlines
jue. 1/85:59 pmORD - KIN
1 stop17h 14mSpirit Airlines
Deal found 9/14$329
This American Airlines deal was found by Cheapflights users on 9/14. 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.
mar. 10/71:50 pmMBJ - ORD
Nonstop4h 33mAmerican Airlines
sáb. 10/119:45 pmORD - MBJ
1 stop16h 30mAmerican Airlines
Deal found 9/14$338
This Mytrip deal was found by Cheapflights users on 9/14. 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.
jue. 10/212:08 pmKIN - ORD
1 stop10h 40mSpirit Airlines
dom. 10/55:05 amORD - KIN
1 stop6h 04mSpirit Airlines
Deal found 9/14$340
This United Airlines deal was found by Cheapflights users on 9/15. 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.
mar. 11/252:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
lun. 12/18:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
Deal found 9/15$340
This American Airlines deal was found by Cheapflights users on 9/15. 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.
mar. 11/252:14 pmMBJ - ORD
Nonstop4h 36mAmerican Airlines
lun. 12/17:11 amORD - MBJ
1 stop6h 39mAmerican Airlines
Deal found 9/15$344
This Mytrip deal was found by Cheapflights users on 9/13. 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.
jue. 10/1612:14 pmKIN - ORD
1 stop11h 31mSpirit Airlines
lun. 10/205:05 amORD - KIN
1 stop6h 04mSpirit Airlines
Deal found 9/13$345
This Delta deal was found by Cheapflights users on 9/15. 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.
mar. 11/255:59 pmMBJ - ORD
1 stop7h 03mDelta
lun. 12/19:46 amORD - MBJ
1 stop5h 48mDelta
Deal found 9/15$345
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
sáb. 9/2712:08 pmKIN - ORD
1 stop10h 40mSpirit Airlines
mar. 9/306:44 pmORD - KIN
1 stop16h 18mSpirit Airlines
Deal found 9/13$352
This Delta deal was found by Cheapflights users on 9/14. 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.
jue. 10/99:00 amKIN - ORD
1 stop7h 41mDelta
jue. 1/87:00 amORD - KIN
2 stops12h 00mDelta
Deal found 9/14$388
This Southwest deal was found by Cheapflights users on 9/15. 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.
mar. 11/253:25 pmMBJ - MDW
2 stops9h 25mSouthwest
lun. 12/15:20 amMDW - MBJ
1 stop6h 30mSouthwest
Deal found 9/15$394

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 septiembre 15, 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

mar. 10/7

12:09 pm-11:45 pm

1 stop11h 36m

Chicago O'Hare Intl

sáb. 10/11

7:43 pm-11:00 am

1 stop15h 17m

$239

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

jue. 10/2

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

dom. 10/5

5:05 am-11:00 am

1 stop5h 55m

$249

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

jue. 10/9

12:14 pm-11:45 pm

1 stop11h 31m

Chicago O'Hare Intl

jue. 1/8

5:59 pm-12:13 pm

1 stop17h 14m

$329

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 11/25

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

lun. 12/1

8:42 am-1:46 pm

Nonstop4h 04m

$340

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

jue. 10/2

12:08 pm-10:48 pm

1 stop10h 40m

Chicago O'Hare Intl

dom. 10/5

5:05 am-11:09 am

1 stop6h 04m

$340

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 11/25

3:13 pm-6:54 pm

Nonstop4h 41m

Chicago O'Hare Intl

dom. 11/30

12:19 am-2:12 pm

1 stop12h 53m

$344

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 11/25

5:59 pm-12:02 am

1 stop7h 03m

Chicago O'Hare Intl

lun. 12/1

9:46 am-4:34 pm

1 stop5h 48m

$345

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

jue. 10/30

12:14 pm-1:03 am

1 stop12h 49m

Chicago O'Hare Intl

jue. 11/6

5:59 pm-12:13 pm

1 stop17h 14m

$345

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

jue. 10/16

12:14 pm-11:45 pm

1 stop11h 31m

Chicago O'Hare Intl

lun. 10/20

5:05 am-11:09 am

1 stop6h 04m

$345

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 10/7

12:10 pm-8:01 am

2 stops19h 51m

Chicago O'Hare Intl

sáb. 10/11

6:58 pm-11:00 am

2 stops16h 02m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 46 results
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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 septiembre 15, 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 septiembre 15, 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
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,015 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Jamaica to Illinois?

    Airlines like Spirit Airlines, Southwest, and Frontier fly from Jamaica to Illinois in about 9h 05m. The time it takes to get you to your destination can typically vary by up to 2h 31m. Airlines will cover a distance of 1709 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $193. However, be on the lookout for offers from Southwest and United Airlines, 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

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Alternative routes for Jamaica to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$369FlexibilityNo cancel feeOn-time65%
DeltaCheapest$322Average$588FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$348Average$525FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$392Average$550FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$409Average$484FlexibilityNo cancel feeOn-time69%

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