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Caribbean

$103+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 29, 2025.

Round-trip from

$205
(Delta)

One-way from

$103
(United Airlines)

Popular in

December

Cheapest in

September

Average price

$377

Good round-trip deal

$280 or less

Good one-way deal

$126 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 ($54 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 29, 2025.

This Delta deal was found by Cheapflights users on 7/27. 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.
Sat 9/201:26 pmSTL - SJU
1 stop7h 34mDelta
Fri 9/265:41 pmSJU - STL
1 stop6h 43mDelta
Deal found 7/27$205
This FlightHub deal was found by Cheapflights users on 7/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/198:12 pmORD - STT
2 stops16h 36mSpirit Airlines
Tue 8/262:43 pmSTT - ORD
1 stop8h 39mSpirit Airlines
Deal found 7/28$213
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/308:47 pmORD - SJU
1 stop17h 20mMultiple Airlines
Fri 9/53:39 amSJU - ORD
1 stop12h 38mMultiple Airlines
Deal found 7/29$227
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/66:44 pmORD - SJU
1 stop15h 20mSpirit Airlines
Sat 9/203:19 pmSJU - ORD
1 stop7h 39mSpirit Airlines
Deal found 7/29$228
This Cheapflightsfares deal was found by Cheapflights users on 7/27. 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 9/136:15 amMDW - SJU
1 stop6h 56mFrontier
Fri 9/263:39 amSJU - MDW
1 stop7h 12mFrontier
Deal found 7/27$236
This Frontier deal was found by Cheapflights users on 7/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/912:20 pmORD - SJU
1 stop11h 07mFrontier
Mon 8/113:34 amSJU - ORD
1 stop7h 40mFrontier
Deal found 7/27$238
This Priceline deal was found by Cheapflights users on 7/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/135:40 pmSTL - SJU
1 stop14h 24mFrontier
Sat 8/169:30 pmSJU - STL
1 stop27h 17mFrontier
Deal found 7/29$239
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/191:57 pmSTL - SJU
1 stop11h 37mMultiple Airlines
Wed 9/241:59 amSJU - STL
2 stops9h 51mMultiple Airlines
Deal found 7/29$247
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/242:30 pmSTL - SJU
2 stops9h 26mSpirit Airlines
Thu 8/282:11 amSJU - STL
2 stops12h 21mSpirit Airlines
Deal found 7/29$249
This Southwest deal was found by Cheapflights users on 7/27. 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.
Fri 9/192:00 pmSTL - SJU
1 stop8h 50mSouthwest
Sun 9/2110:30 pmSJU - STL
1 stop11h 00mSouthwest
Deal found 7/27$260
This FlightHub deal was found by Cheapflights users on 7/27. 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.
Wed 10/85:05 amORD - PUJ
1 stop8h 09mSpirit Airlines
Wed 10/153:19 pmPUJ - ORD
1 stop9h 26mSpirit Airlines
Deal found 7/27$298
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Sat 8/236:00 amSTL - SJU
1 stop15h 49mAmerican Airlines
Sat 8/306:00 amSJU - STL
2 stops11h 14mAmerican Airlines
Deal found 7/29$300

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 29, 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

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 9/20

1:26 pm-10:00 pm

1 stop7h 34m

San Juan Luis Munoz Marin Intl

Fri 9/26

5:41 pm-11:24 pm

1 stop6h 43m

$205

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 8/19

8:12 pm-1:48 pm

2 stops16h 36m

Saint Thomas Island Cyril E King

Tue 8/26

2:43 pm-10:22 pm

1 stop8h 39m

$213

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/30

8:47 pm-3:07 pm

1 stop17h 20m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-3:17 pm

1 stop12h 38m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 9/6

6:44 pm-11:04 am

1 stop15h 20m

San Juan Luis Munoz Marin Intl

Sat 9/13

3:19 pm-9:58 pm

1 stop7h 39m

$228

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/30

10:51 am-7:18 pm

1 stop7h 27m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-9:51 am

1 stop7h 12m

$235

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/9

12:20 pm-12:27 am

1 stop11h 07m

San Juan Luis Munoz Marin Intl

Mon 8/11

3:34 am-10:14 am

1 stop7h 40m

$238

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Wed 8/13

5:40 pm-9:04 am

1 stop14h 24m

San Juan Luis Munoz Marin Intl

Sat 8/16

9:30 pm-11:47 pm

1 stop27h 17m

$239

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Fri 9/19

1:57 pm-2:34 am

1 stop11h 37m

San Juan Luis Munoz Marin Intl

Wed 9/24

1:59 am-10:50 am

2 stops9h 51m

$247

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sun 8/24

2:30 pm-12:56 am

2 stops9h 26m

San Juan Luis Munoz Marin Intl

Thu 8/28

2:11 am-1:32 pm

2 stops12h 21m

$249

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Fri 9/19

2:00 pm-11:50 pm

1 stop8h 50m

San Juan Luis Munoz Marin Intl

Sun 9/21

10:30 pm-8:30 am

1 stop11h 00m

$260

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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 29, 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 29, 2025.

The most flights from USIL to 0CB are scheduled on a Monday (9 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 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 29, 2025.
See what other customers who have flown with Southwest, Delta, and Copa Airlines 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
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Copa Airlines
7.5
Good
1,493 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,899 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 United Airlines ($103), Frontier ($106), and Spirit Airlines ($108).

  • 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

Browse thousands of different options on Cheapflights for your next trip

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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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$357FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$379FlexibilityNo cancel feeOn-time65%
DeltaCheapest$190Average$614FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$193Average$476FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$194Average$663FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$226Average$662FlexibilityNo cancel feeOn-time69%
ArajetCheapest$235Average$315FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$261Average$481FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$335Average$750FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$352Average$648FlexibilityNo cancel feeOn-time63%

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