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Illinois

$171+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — ORD
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Priceline deal was found by Cheapflights users on 10/30. 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.
Thu 11/131:07 pmMBJ - ORD
1 stop8h 20mSpirit Airlines
Sun 11/165:10 amORD - MBJ
1 stop5h 52mSpirit Airlines
Deal found 10/30$287
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 12/122:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
Fri 1/28:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
Deal found 10/28$320
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sun 11/232:14 pmMBJ - ORD
Nonstop4h 36mAmerican Airlines
Sun 11/3011:59 pmORD - MBJ
1 stop14h 00mAmerican Airlines
Deal found 10/28$330
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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.
Sun 11/231:07 pmMBJ - ORD
1 stop11h 06mSpirit Airlines
Sun 11/305:00 amORD - MBJ
1 stop6h 02mSpirit Airlines
Deal found 10/28$337
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/262:14 pmMBJ - ORD
Nonstop4h 36mAmerican Airlines
Wed 12/310:15 amORD - MBJ
Nonstop4h 07mAmerican Airlines
Deal found 10/29$351
This Mytrip deal was found by Cheapflights users on 10/28. 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 11/252:24 pmKIN - ORD
1 stop9h 49mSpirit Airlines
Tue 12/25:00 amORD - KIN
1 stop7h 21mSpirit Airlines
Deal found 10/28$360
This United Airlines deal was found by Cheapflights users on 10/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/202:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
Sun 11/238:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
Deal found 10/30$380
This Delta deal was found by Cheapflights users on 10/30. 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 11/259:00 amKIN - ORD
1 stop7h 26mDelta
Thu 11/276:45 amORD - KIN
2 stops12h 15mDelta
Deal found 10/30$388
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/11:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
Wed 12/36:00 amORD - MBJ
1 stop7h 29mUnited Airlines
Deal found 10/29$393
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Tue 11/252:24 pmKIN - ORD
1 stop9h 49mMultiple Airlines
Tue 12/24:22 pmORD - KIN
2 stops42h 52mMultiple Airlines
Deal found 10/28$397
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/257:30 amKIN - ORD
2 stops9h 35mAmerican Airlines
Tue 12/210:15 amORD - KIN
2 stops10h 58mAmerican Airlines
Deal found 10/28$402
This OneTravel deal was found by Cheapflights users on 10/29. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/121:19 pmKIN - ORD
1 stop7h 42mSpirit Airlines
Wed 12/315:00 amORD - KIN
1 stop6h 14mSpirit Airlines
Deal found 10/29$408

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$287
(Priceline)

One-way from

$171
(Gotogate)

Popular in

January

Cheapest in

September

Good round-trip deal

$264 or less

Good one-way deal

$234 or less
Provider with most accurate pricing for Montego Bay Sangster Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-Chicago (CHI) flights.
Search Deals
From Jamaica to Illinois
Search Deals
One-way flight from Jamaica to Illinois
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($75 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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

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 October 30, 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

Thu 11/13

1:07 pm-11:06 pm

2 stops10h 59m

Chicago O'Hare Intl

Sun 11/16

5:10 am-12:02 pm

1 stop5h 52m

$319

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 12/12

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Fri 1/2

8:42 am-1:46 pm

Nonstop4h 04m

$320

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 11/13

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Sun 11/16

8:42 am-1:46 pm

Nonstop4h 04m

$320

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sun 11/23

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Sun 11/30

8:42 am-1:46 pm

Nonstop4h 04m

$320

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 1/9

2:16 pm-9:04 pm

1 stop7h 48m

Chicago O'Hare Intl

Mon 1/12

5:33 am-8:36 pm

1 stop14h 03m

$326

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sun 11/23

2:14 pm-5:50 pm

Nonstop4h 36m

Chicago O'Hare Intl

Sun 11/30

11:59 pm-2:59 pm

1 stop14h 00m

$330

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 11/25

2:24 pm-11:13 pm

1 stop9h 49m

Chicago O'Hare Intl

Tue 12/2

5:00 am-1:21 pm

1 stop7h 21m

$360

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 1/9

5:06 pm-11:25 pm

1 stop7h 19m

Chicago Midway

Mon 1/12

2:01 pm-12:05 pm

2 stops21h 04m

$385

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 11/25

9:00 am-4:46 pm

1 stop8h 46m

Chicago O'Hare Intl

Thu 11/27

11:19 am-8:00 pm

1 stop7h 41m

$388

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 11/26

9:00 am-6:52 pm

1 stop10h 52m

Chicago O'Hare Intl

Wed 12/3

6:45 am-8:06 pm

2 stops12h 21m

$388

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 44 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, December is the cheapest month in which you can book a flight from Jamaica to Illinois (average of $251). Flying from Jamaica to Illinois in April is currently the most expensive (average of $440). 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 October 30, 2025.

It’s optimal to fly from Jamaica to Illinois at noon. By choosing this option you can save up to 32% on the cost of your flight, compared to a flight in the evening.

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 October 30, 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
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

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
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

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
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

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
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

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
8,116 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

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, United Airlines, and Delta fly from Jamaica to Illinois in about 4h 25m. The time it takes to get you to your destination can typically vary by up to 6h 34m. Airlines will cover a distance of 1724 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 United Airlines, with whom users have recently found tickets for as low as $203. However, be on the lookout for offers from Southwest 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, December is the cheapest month in which you can book a flight from Jamaica to Illinois (average of $251). Flying from Jamaica to Illinois in April is currently the most expensive (average of $440). 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 Jamaica to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Jamaica to Illinois

Discover the top 4 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$361FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$348Average$508FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$392Average$536FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$409Average$484FlexibilityNo cancel feeOn-time69%

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