HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$103+ Cheap flights from Illinois to Caribbean Islands

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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Illinois to Caribbean Islands

Keep the following information in mind while searching for Illinois to Caribbean Islands flight deals. Data was last updated April 24, 2025.

Round-trip from

$202
(Cheapflightsfares)

One-way from

$103
(FlightHub)

Popular in

December

Cheapest in

August

Average price

$352
From Illinois to Caribbean Islands
Search Deals
One-way flight from Illinois to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

Find flight deals from Illinois to Caribbean Islands

Cheapest flights from Illinois to Caribbean Islands
Explore the most affordable flight options available from Illinois to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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 5/107:47 amORD - SJU
1 stop16h 07mSpirit Airlines
Thu 5/151:33 amSJU - ORD
1 stop18h 44mSpirit Airlines
Deal found 4/22$196
This Delta deal was found by Cheapflights users on 4/23. 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 9/226:00 amSTL - SJU
1 stop6h 23mDelta
Sat 9/275:19 pmSJU - STL
1 stop7h 20mDelta
Deal found 4/23$209
This United Airlines deal was found by Cheapflights users on 4/22. 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 9/196:15 amSTL - SJU
1 stop8h 27mUnited Airlines
Thu 9/252:55 pmSJU - STL
1 stop8h 05mUnited Airlines
Deal found 4/22$229
This Booking.com deal was found by Cheapflights users on 4/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/104:35 pmORD - SJU
1 stop17h 10mMultiple Airlines
Thu 5/1510:46 amSJU - ORD
1 stop13h 25mMultiple Airlines
Deal found 4/23$238
This Mytrip deal was found by Cheapflights users on 4/24. 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.
Sat 5/1010:10 amSTL - SJU
1 stop7h 57mSpirit Airlines
Sat 5/178:12 pmSJU - STL
1 stop14h 03mSpirit Airlines
Deal found 4/24$272
This Booking.com deal was found by Cheapflights users on 4/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1710:10 amSTL - SJU
1 stop7h 57mMultiple Airlines
Sat 5/179:30 pmSJU - STL
1 stop27h 36mMultiple Airlines
Deal found 4/23$274
This American Airlines deal was found by Cheapflights users on 4/23. 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 9/225:31 amSTL - SJU
1 stop6h 14mAmerican Airlines
Sat 9/278:30 amSJU - STL
2 stops12h 53mAmerican Airlines
Deal found 4/23$290
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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 5/26:15 amMDW - SJU
1 stop7h 32mFrontier
Thu 5/86:00 amSJU - MDW
1 stop7h 24mFrontier
Deal found 4/23$294
This Frontier deal was found by Cheapflights users on 4/23. 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.
Fri 5/29:00 amORD - SJU
1 stop8h 47mFrontier
Sun 5/410:46 amSJU - ORD
1 stop13h 25mFrontier
Deal found 4/23$298
This CheapOair deal was found by Cheapflights users on 4/22. 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 5/35:45 pmSTL - SJU
1 stop18h 44mFrontier
Fri 5/93:56 amSJU - STL
1 stop21h 10mFrontier
Deal found 4/22$298
This CheapOair deal was found by Cheapflights users on 4/23. 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.
Tue 5/206:10 amORD - PUJ
Nonstop4h 41mMultiple Airlines
Sat 5/243:22 pmPUJ - ORD
1 stop9h 43mMultiple Airlines
Deal found 4/23$299
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/32:53 pmORD - PUJ
1 stop19h 25mAmerican Airlines
Fri 5/94:53 pmPUJ - ORD
1 stop19h 16mAmerican Airlines
Deal found 4/23$304

Cheapflights Fare Finder

Customize your flight search to find flights from Illinois to Caribbean Islands 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 April 24, 2025.
Use the filters below to find and compare flights from Illinois to Caribbean Islands that are best for you.

Fly from

Illinois

Fly to

Caribbean Islands

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/10

7:47 am-12:54 am

1 stop16h 07m

San Juan Luis Munoz Marin Intl

Thu 5/15

1:33 am-7:17 pm

1 stop18h 44m

$196

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Mon 9/22

6:00 am-1:23 pm

1 stop6h 23m

San Juan Luis Munoz Marin Intl

Sat 9/27

5:19 pm-11:39 pm

1 stop7h 20m

$209

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Fri 9/19

6:15 am-3:42 pm

1 stop8h 27m

San Juan Luis Munoz Marin Intl

Thu 9/25

2:55 pm-10:00 pm

1 stop8h 05m

$229

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/10

4:35 pm-10:45 am

1 stop17h 10m

San Juan Luis Munoz Marin Intl

Thu 5/15

10:46 am-11:11 pm

1 stop13h 25m

$238

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 5/10

10:10 am-7:07 pm

1 stop7h 57m

San Juan Luis Munoz Marin Intl

Sat 5/17

8:12 pm-9:15 am

1 stop14h 03m

$272

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 5/17

10:10 am-7:07 pm

1 stop7h 57m

San Juan Luis Munoz Marin Intl

Sat 5/17

9:30 pm-12:06 am

1 stop27h 36m

$274

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Mon 9/22

5:31 am-12:45 pm

1 stop6h 14m

San Juan Luis Munoz Marin Intl

Sat 9/27

8:30 am-8:23 pm

2 stops12h 53m

$290

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 5/2

6:15 am-2:47 pm

1 stop7h 32m

San Juan Luis Munoz Marin Intl

Thu 5/8

6:00 am-12:24 pm

1 stop7h 24m

$294

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 5/2

4:15 pm-12:05 am

1 stop6h 50m

San Juan Luis Munoz Marin Intl

Mon 5/5

6:00 am-6:29 pm

1 stop13h 29m

$298

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Mon 5/5

5:45 pm-2:51 am

1 stop8h 06m

San Juan Luis Munoz Marin Intl

Sat 5/10

12:05 pm-12:06 am

1 stop13h 01m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Illinois to Caribbean Islands

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

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

Currently, September is the cheapest month in which you can book a flight from Illinois to Caribbean Islands (average of $254). Flying from Illinois to Caribbean Islands in December is currently the most expensive (average of $336). 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 EPX?

Find hourly flight availability from Illinois to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 24, 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 Islands as you normally would.

Weekly flight availability from Illinois to Caribbean Islands

Explore weekly flight availability from Illinois to Caribbean Islands. 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 April 24, 2025.

The most flights from USIL to zzEPX 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).

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated April 24, 2025.
Read through reviews of airlines operating flights from Illinois to Caribbean Islands, such as Delta, Alaska Airlines and Southwest. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,920 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Alaska Airlines
8.0
Very good
9,918 reviews
Delta
8.0
Very good
7,920 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Southwest
8.0
Very good
4,286 reviews
Delta
8.0
Very good
7,920 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Copa Airlines
7.6
Good
1,411 reviews
Delta
8.0
Very good
7,920 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
LATAM Airlines
7.5
Good
1,765 reviews
Delta
8.0
Very good
7,920 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

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

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $103. Frontier flights start at $105 while deals on Delta start at $105 one-way.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Illinois to Caribbean Islands (average of $254). Flying from Illinois to Caribbean Islands in December is currently the most expensive (average of $336). 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 Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to Fort Lauderdale flights
Los Angeles to John F Kennedy Intl flights
Newark to Miami flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to Miami flights
John F Kennedy Intl to Los Angeles flights
LaGuardia to Miami flights
Newark to Orlando flights
Dallas/Fort Worth to John F Kennedy Intl flights
Newark to Los Angeles flights
Newark to Cancún flights
John F Kennedy Intl to Dallas/Fort Worth flights
San Francisco to John F Kennedy Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to Honolulu flights
Seattle to Los Angeles flights
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to LaGuardia flights
Los Angeles to Seattle flights
Los Angeles to Newark flights
John F Kennedy Intl to Fort Lauderdale flights
Dallas/Fort Worth to Cancún flights
John F Kennedy Intl to Cancún flights
Dallas/Fort Worth to Seattle flights
John F Kennedy Intl to San Francisco flights
O'Hare Intl to Dallas/Fort Worth flights
John F Kennedy Intl to Las Vegas flights
LaGuardia to Dallas/Fort Worth flights
San Francisco to Newark flights
Newark to Las Vegas flights
Dallas/Fort Worth to Newark flights
Newark to Dallas/Fort Worth flights
John F Kennedy Intl to Orlando flights
Newark to Seattle flights
John F Kennedy Intl to Seattle flights
Los Angeles to Dallas/Fort Worth flights
O'Hare Intl to LaGuardia flights
LaGuardia to Atlanta flights
Los Angeles to LaGuardia flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Cancún flights
LaGuardia to Orlando flights
Newark to San Francisco flights
Newark to Hobby flights
George Bush Intcntl to Cancún flights
Newark to O'Hare Intl flights
Atlanta to LaGuardia flights
San Jose to Los Angeles flights
John F Kennedy Intl to Hobby flights

Top 10 airlines flying from Illinois to Caribbean Islands

Discover the top 10 airlines that operate flights from Illinois to Caribbean Islands. 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$374FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$142Average$362FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$193Average$537FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$194Average$674FlexibilityNo cancel feeOn-time71%
DeltaCheapest$222Average$654FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$226Average$672FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$293Average$502FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$335Average$780FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$343Average$675FlexibilityNo cancel feeOn-time63%
AviancaCheapest$397Average$953FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.