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Jamaica

$128+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MBJ
Jun 13 — Jun 201
Sat 6/13
Sat 6/20
1 adult, Economy
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Cheap 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 May 14, 2026.

This JetBlue deal was found by Cheapflights users on 5/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/257:00 am
ORD
-
MBJ
1 stop10h 33m
JetBlue
Thu 8/2712:55 pm
MBJ
-
ORD
1 stop10h 49m
JetBlue
Deal found 5/9$324
This Super.com deal was found by Cheapflights users on 5/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:00 am
ORD
-
MBJ
1 stop10h 33m
JetBlue
Wed 8/2612:55 pm
MBJ
-
ORD
1 stop10h 49m
JetBlue
Deal found 5/12$328
This Super.com deal was found by Cheapflights users on 5/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:00 am
ORD
-
MBJ
1 stop10h 33m
JetBlue
Fri 8/2112:55 pm
MBJ
-
ORD
1 stop10h 49m
JetBlue
Deal found 5/11$329
This Super.com deal was found by Cheapflights users on 5/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:00 am
ORD
-
MBJ
1 stop10h 33m
JetBlue
Sat 9/123:10 pm
MBJ
-
ORD
1 stop8h 34m
JetBlue
Deal found 5/10$330
This Super.com deal was found by Cheapflights users on 5/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:00 am
ORD
-
MBJ
1 stop6h 51m
JetBlue
Thu 9/173:10 pm
MBJ
-
ORD
1 stop8h 34m
JetBlue
Deal found 5/11$331
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:45 am
ORD
-
MBJ
Nonstop4h 16m
American Airlines
Tue 11/103:14 pm
MBJ
-
ORD
Nonstop4h 41m
American Airlines
Deal found 5/13$338
This American Airlines deal was found by Cheapflights users on 5/12. 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 12/138:10 am
ORD
-
MBJ
Nonstop4h 10m
American Airlines
Sun 12/202:21 pm
MBJ
-
ORD
Nonstop4h 43m
American Airlines
Deal found 5/12$343
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:35 pm
ORD
-
MBJ
1 stop14h 33m
American Airlines
Sun 11/153:14 pm
MBJ
-
ORD
Nonstop4h 41m
American Airlines
Deal found 5/13$347
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/179:10 am
ORD
-
MBJ
Nonstop4h 07m
American Airlines
Mon 8/245:13 pm
MBJ
-
ORD
1 stop14h 21m
American Airlines
Deal found 5/13$348
This JetBlue deal was found by Cheapflights users on 5/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:00 am
ORD
-
MBJ
1 stop10h 33m
JetBlue
Fri 9/412:55 pm
MBJ
-
ORD
1 stop10h 49m
JetBlue
Deal found 5/12$351
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:38 pm
PIA
-
MBJ
2 stops18h 34m
American Airlines
Mon 12/74:23 pm
MBJ
-
PIA
2 stops18h 48m
American Airlines
Deal found 5/13$357
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Thu 12/38:11 pm
BMI
-
MBJ
2 stops18h 42m
American Airlines
Mon 12/74:23 pm
MBJ
-
BMI
2 stops19h 27m
American Airlines
Deal found 5/14$357

Find flight deals from Illinois to Jamaica

Keep the following information in mind while searching for Illinois to Jamaica flight deals. Data was last updated May 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$324
(JetBlue)

One-way from

$128
(Super.com)

Popular in

June

Cheapest in

April

Average price

$541

Good round-trip deal

$317 or less

Good one-way deal

$138 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
Search Deals
From Illinois to Jamaica
Search Deals
One-way flight from Illinois to Jamaica
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Illinois to Jamaica.
Search Deals
Price to beat on a one-way flight from Illinois to Jamaica.
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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 May 14, 2026.
Use the filters below to find and compare flights from Illinois to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 8/31

7:00 am-5:33 pm

1 stop10h 33m

Montego Bay Sangster Intl

Fri 9/4

12:55 pm-11:44 pm

1 stop10h 49m

$351

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 8/1

6:30 am-3:26 pm

1 stop8h 56m

Montego Bay Sangster Intl

Sat 8/8

4:33 pm-12:45 am

1 stop8h 12m

$352

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 10/27

6:00 am-1:29 pm

1 stop7h 29m

Montego Bay Sangster Intl

Sun 11/1

3:20 pm-12:15 am

1 stop9h 55m

$352

PeoriaMontego Bay

PIA - MBJ

PIAMBJ

Greater Peoria

Wed 7/1

4:20 pm-11:47 am

2 stops19h 27m

Montego Bay Sangster Intl

Wed 7/8

2:36 pm-12:22 am

1 stop9h 46m

$362

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 6/10

6:30 am-1:30 pm

1 stop7h 00m

Montego Bay Sangster Intl

Wed 6/17

4:12 pm-11:26 pm

1 stop7h 14m

$432

MolineMontego Bay

MLI - MBJ

MLIMBJ

Moline Quad-City

Sat 6/27

4:24 pm-1:08 pm

2 stops20h 44m

Montego Bay Sangster Intl

Sat 7/4

5:14 pm-11:23 am

2 stops18h 09m

$439

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 11/7

6:00 am-4:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

Wed 11/11

3:40 pm-9:45 pm

1 stop7h 05m

$452

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 9/8

6:00 am-11:49 am

1 stop5h 49m

Montego Bay Sangster Intl

Sat 9/12

1:25 pm-9:46 pm

1 stop8h 21m

$452

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 8/21

9:52 am-3:34 pm

1 stop5h 42m

Montego Bay Sangster Intl

Tue 8/25

4:59 pm-7:56 am

2 stops14h 57m

$457

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 7/18

3:21 pm-10:11 am

1 stop18h 50m

Montego Bay Sangster Intl

Fri 7/24

11:16 am-12:01 am

1 stop12h 45m

$468

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/9

Showing 1-10 of 60 resultsSorted by cheapest first
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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

How far ahead should I book a flight from Illinois to Jamaica?

To ensure you get the cheapest price possible for a flight from Illinois to Jamaica, you should look to book at least 58 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, December is the cheapest month in which you can book a flight from Illinois to Jamaica (average of $84). Flying from Illinois to Jamaica in September is currently the most expensive (average of $238). 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 May 14, 2026.

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 May 14, 2026.

The most flights from USIL to JM0 are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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.

  • How long is the flight from Illinois to Jamaica?

    Airlines like JetBlue, United Airlines, and American Airlines fly from Illinois to Jamaica in about 8h 56m. The time it takes to get you to your destination can typically vary by up to 10h 31m. There are 1724 mi between Illinois and Jamaica. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Illinois to Jamaica one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $108. Spirit Airlines flights start at $127 while deals on American Airlines start at $138 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, December is the cheapest month in which you can book a flight from Illinois to Jamaica (average of $84). Flying from Illinois to Jamaica in September is currently the most expensive (average of $238). 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.
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Top 7 airlines flying from Illinois to Jamaica

Discover the top 7 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 May 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$100Average$457FlexibilityNo cancel feeOn-time65%
FrontierCheapest$144Average$653FlexibilityNo cancel feeOn-time62%
DeltaCheapest$178Average$537FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$297Average$452FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$302Average$523FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$319Average$645FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$468Average$646FlexibilityNo cancel feeOn-time63%

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