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Caribbean

$114+ Cheap flights from Illinois to Caribbean

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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Jul 21 — Jul 281
Mon 7/21
Mon 7/28
1 adult, Economy
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Cheap flight deals from Illinois to Caribbean

Keep the following information in mind while searching for Illinois to Caribbean flight deals. Data was last updated July 16, 2025.

Round-trip from

$218
(Spirit)

One-way from

$114
(Priceline)

Popular in

December

Cheapest in

September

Average price

$385

Good round-trip deal

$260 or less

Good one-way deal

$146 or less
From Illinois to Caribbean
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One-way flight from Illinois to Caribbean
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Highest demand for flights based on searches. 12% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Illinois to Caribbean.
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Price to beat on a one-way flight from Illinois to Caribbean.
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Find flight deals from Illinois to Caribbean

Cheapest flights from Illinois to Caribbean
Explore the most affordable flight options available from Illinois to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 16, 2025.

This Spirit deal was found by Cheapflights users on 7/15. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/36:23 pmORD - SJU
Nonstop4h 43mSpirit Airlines
Fri 8/83:50 pmSJU - ORD
1 stop16h 14mSpirit Airlines
Deal found 7/15$218
This Priceline deal was found by Cheapflights users on 7/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/186:20 amMDW - SJU
1 stop6h 58mFrontier
Fri 8/223:21 pmSJU - MDW
1 stop9h 06mFrontier
Deal found 7/14$220
This Priceline deal was found by Cheapflights users on 7/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/117:45 amORD - SJU
1 stop7h 58mFrontier
Thu 8/217:25 amSJU - ORD
1 stop12h 03mFrontier
Deal found 7/14$225
This Delta deal was found by Cheapflights users on 7/14. 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.
Tue 9/1610:35 amMDW - SJU
1 stop10h 25mDelta
Fri 9/1912:58 pmSJU - MDW
1 stop9h 38mDelta
Deal found 7/14$233
This Delta deal was found by Cheapflights users on 7/15. 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.
Mon 11/36:00 amORD - SJU
1 stop9h 18mDelta
Fri 11/76:20 pmSJU - ORD
1 stop7h 33mDelta
Deal found 7/15$243
This FlightHub deal was found by Cheapflights users on 7/16. 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.
Mon 8/2510:26 amORD - SJU
1 stop10h 22mMultiple Airlines
Sat 8/303:21 pmSJU - ORD
1 stop9h 12mMultiple Airlines
Deal found 7/16$253
This Cheapflightsfares deal was found by Cheapflights users on 7/16. 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.
Wed 11/56:05 amORD - STT
1 stop7h 06mSpirit Airlines
Wed 11/124:06 pmSTT - ORD
1 stop7h 17mSpirit Airlines
Deal found 7/16$258
This Cheapflightsfares deal was found by Cheapflights users on 7/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/235:05 amORD - PUJ
1 stop8h 55mSpirit Airlines
Wed 8/274:05 pmPUJ - ORD
1 stop8h 54mSpirit Airlines
Deal found 7/15$316
This Kiwi.com deal was found by Cheapflights users on 7/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/97:39 pmORD - PUJ
1 stop16h 06mMultiple Airlines
Sat 11/155:47 amPUJ - ORD
Nonstop5h 10mMultiple Airlines
Deal found 7/15$318
This Kiwi.com deal was found by Cheapflights users on 7/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/56:45 amORD - PUJ
Nonstop4h 40mFrontier
Wed 8/135:08 pmPUJ - ORD
Nonstop5h 08mFrontier
Deal found 7/15$327
This American Airlines deal was found by Cheapflights users on 7/16. 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 8/118:35 amORD - PUJ
Nonstop4h 40mAmerican Airlines
Wed 8/203:30 pmPUJ - ORD
Nonstop5h 00mAmerican Airlines
Deal found 7/16$328
This Southwest deal was found by Cheapflights users on 7/15. 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.
Mon 8/115:05 amMDW - PUJ
1 stop7h 50mSouthwest
Wed 8/202:50 pmPUJ - MDW
1 stop7h 50mSouthwest
Deal found 7/15$343

Cheapflights Fare Finder

Customize your flight search to find flights from Illinois to Caribbean 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 July 16, 2025.
Use the filters below to find and compare flights from Illinois to Caribbean that are best for you.

Fly from

Illinois

Fly to

Caribbean

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/3

6:23 pm-12:06 am

Nonstop4h 43m

San Juan Luis Munoz Marin Intl

Fri 8/8

3:50 pm-7:04 am

1 stop16h 14m

$218

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 8/18

6:20 am-2:18 pm

1 stop6h 58m

San Juan Luis Munoz Marin Intl

Fri 8/22

3:21 pm-11:27 pm

1 stop9h 06m

$220

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 8/11

7:45 am-4:43 pm

1 stop7h 58m

San Juan Luis Munoz Marin Intl

Thu 8/21

7:25 am-6:28 pm

1 stop12h 03m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 9/16

10:35 am-10:00 pm

1 stop10h 25m

San Juan Luis Munoz Marin Intl

Fri 9/19

12:58 pm-9:36 pm

1 stop9h 38m

$233

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 9/8

7:00 am-4:27 pm

1 stop8h 27m

San Juan Luis Munoz Marin Intl

Sat 9/13

7:30 am-4:31 pm

1 stop10h 01m

$243

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 8/25

10:26 am-9:48 pm

1 stop10h 22m

San Juan Luis Munoz Marin Intl

Sat 8/30

3:21 pm-11:33 pm

1 stop9h 12m

$253

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Mon 8/18

6:56 am-3:19 pm

1 stop7h 23m

Saint Thomas Island Cyril E King

Mon 8/25

2:43 pm-10:22 pm

1 stop8h 39m

$260

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 8/23

5:05 am-3:00 pm

1 stop8h 55m

Punta Cana

Wed 8/27

4:05 pm-11:59 pm

1 stop8h 54m

$316

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 8/5

6:45 am-12:25 pm

Nonstop4h 40m

Punta Cana

Wed 8/13

5:08 pm-9:16 pm

Nonstop5h 08m

$327

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 8/11

6:45 am-12:25 pm

Nonstop4h 40m

Punta Cana

Wed 8/20

4:05 pm-11:59 pm

1 stop8h 54m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/14

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

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

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

Currently, September is the cheapest month in which you can book a flight from Illinois to Caribbean (average of $254). Flying from Illinois to Caribbean in June is currently the most expensive (average of $339). 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 CB?

Find hourly flight availability from Illinois to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Caribbean as you normally would.

Weekly flight availability from Illinois to Caribbean

Explore weekly flight availability from Illinois to Caribbean. 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 July 16, 2025.

The most flights from USIL to 0CB are scheduled on a Monday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 on average).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated July 16, 2025.
See what other customers who have flown with Southwest, Delta, and KLM from Illinois to Caribbean 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.
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,959 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
KLM
7.8
Good
1,373 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Copa Airlines
7.5
Good
1,483 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,863 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

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

    The cheapest airlines for a one-way flight from Illinois to Caribbean are Frontier ($114), Spirit Airlines ($115), and Delta ($117).

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Illinois to Caribbean (average of $254). Flying from Illinois to Caribbean in June is currently the most expensive (average of $339). 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 Illinois to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 10 airlines flying from Illinois to Caribbean

Discover the top 10 airlines that operate flights from Illinois to Caribbean. 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 July 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$357FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$378FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$193Average$536FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$194Average$656FlexibilityNo cancel feeOn-time71%
DeltaCheapest$216Average$617FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$226Average$667FlexibilityNo cancel feeOn-time69%
ArajetCheapest$234Average$313FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$261Average$481FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$335Average$750FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$352Average$649FlexibilityNo cancel feeOn-time63%

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