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$108+ Cheap flights from Caribbean 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Caribbean to Illinois

Keep the following information in mind while searching for Caribbean to Illinois flight deals. Data was last updated September 11, 2025.

Round-trip from

$181
(Cheapflightsfares)

One-way from

$108
(Southwest)

Popular in

June

Cheapest in

January

Average price

$294

Good round-trip deal

$171 or less

Good one-way deal

$169 or less
From Caribbean to Illinois
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One-way flight from Caribbean to Illinois
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Highest demand for flights based on searches. 2% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 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 Caribbean to Illinois.
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Price to beat on a one-way flight from Caribbean to Illinois.
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Find flight deals from Caribbean to Illinois

Cheapest flights from Caribbean to Illinois
Explore the most affordable flight options available from Caribbean to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/113:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Sat 10/183:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Deal found 9/11$181
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/306:44 amSJU - ORD
1 stop10h 28mSpirit Airlines
Sat 10/46:30 amORD - SJU
1 stop6h 41mSpirit Airlines
Deal found 9/11$186
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/27:40 pmSJU - ORD
Nonstop5h 16mSpirit Airlines
Fri 10/312:55 pmORD - SJU
Nonstop4h 39mSpirit Airlines
Deal found 9/11$187
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/37:40 pmSJU - ORD
Nonstop5h 16mSpirit Airlines
Wed 10/86:00 amORD - SJU
1 stop7h 12mSpirit Airlines
Deal found 9/11$189
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/13:19 pmSJU - ORD
1 stop7h 39mSpirit Airlines
Fri 10/312:55 pmORD - SJU
Nonstop4h 39mSpirit Airlines
Deal found 9/11$192
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/277:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sat 11/12:03 pmORD - SJU
Nonstop4h 39mSpirit Airlines
Deal found 9/10$196
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/13:19 pmSJU - ORD
1 stop7h 39mSpirit Airlines
Sat 10/46:30 amORD - SJU
1 stop6h 41mSpirit Airlines
Deal found 9/10$198
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/73:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Fri 10/109:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/11$200
This Spirit deal was found by Cheapflights users on 9/9. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/83:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Wed 11/196:55 amORD - SJU
Nonstop4h 38mSpirit Airlines
Deal found 9/9$203
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/306:44 amSJU - ORD
1 stop10h 28mSpirit Airlines
Fri 10/312:55 pmORD - SJU
Nonstop4h 39mSpirit Airlines
Deal found 9/11$204
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/243:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Mon 10/279:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/10$208
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/412:10 pmMBJ - ORD
1 stop10h 38mSpirit Airlines
Sat 10/117:43 pmORD - MBJ
1 stop15h 17mSpirit Airlines
Deal found 9/11$223

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean 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 September 11, 2025.
Use the filters below to find and compare flights from Caribbean to Illinois that are best for you.

Fly from

Caribbean

Fly to

Illinois

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 10/4

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Sat 10/11

7:43 pm-11:00 am

1 stop15h 17m

$223

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Wed 10/29

7:05 am-6:20 pm

2 stops12h 15m

Lambert-St Louis

Mon 11/3

8:13 am-8:48 pm

1 stop10h 35m

$230

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 10/7

12:09 pm-6:38 pm

1 stop6h 29m

Chicago O'Hare Intl

Sat 10/11

7:43 pm-11:00 am

1 stop15h 17m

$245

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 9/17

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Tue 9/30

5:05 am-11:05 am

1 stop6h 00m

$252

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 9/18

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Tue 9/30

5:05 am-11:05 am

1 stop6h 00m

$252

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 10/4

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Mon 10/13

5:05 am-11:00 am

1 stop5h 55m

$253

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 10/4

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Tue 10/14

5:05 am-11:00 am

1 stop5h 55m

$253

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 10/8

12:09 pm-6:38 pm

1 stop6h 29m

Chicago O'Hare Intl

Tue 10/14

5:05 am-11:00 am

1 stop5h 55m

$256

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 10/4

3:22 pm-11:41 pm

1 stop9h 19m

Chicago Midway

Tue 10/7

8:05 am-2:30 am

2 stops17h 25m

$262

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 2/14

5:47 am-8:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 2/21

10:27 am-5:12 pm

Nonstop4h 45m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 60 results
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Best time to book a flight from Caribbean to Illinois

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

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

Currently, August is the cheapest month in which you can book a flight from Caribbean to Illinois (average of $245). Flying from Caribbean 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 CB to IL?

Find hourly flight availability from Caribbean 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 September 11, 2025.

When flying from Caribbean 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.

Weekly flight availability from Caribbean to Illinois

Explore weekly flight availability from Caribbean to Illinois. 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 September 11, 2025.

The most flights from 0CB to USIL are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

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 September 11, 2025.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Caribbean to Illinois 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.
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Spirit Airlines
6.3
Okay
8,023 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Frontier
5.8
Fair
3,177 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

Related info for your journey

Find useful and relevant information for your journey from Caribbean 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 Caribbean to Illinois?

    Departing from Caribbean to Illinois will take you 9h 19m. Caribbean and Illinois are separated by a distance of 2057 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $108. Delta flights start at $113 while deals on United Airlines start at $113 one-way.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Caribbean to Illinois (average of $245). Flying from Caribbean 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

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Alternative routes for Caribbean to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Caribbean to Illinois

Discover the top 6 airlines that operate flights from Caribbean 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$135Average$309FlexibilityNo cancel feeOn-time65%
FrontierCheapest$137Average$310FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$421FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$238Average$548FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$505FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$333Average$518FlexibilityNo cancel feeOn-time71%

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