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Caribbean Islands

$98+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Aug 10 — Aug 171
Sun 8/10
Sun 8/17
1 adult, Economy
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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 August 5, 2025.

Round-trip from

$189
(FlightHub)

One-way from

$98
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$326
From Illinois to Caribbean Islands
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One-way flight from Illinois to Caribbean Islands
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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 ($18 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 5, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/5. 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 8/1211:28 amORD - SJU
1 stop14h 11mMultiple Airlines
Fri 8/1510:16 pmSJU - ORD
1 stop12h 06mMultiple Airlines
Deal found 8/5$224
This FlightHub deal was found by Cheapflights users on 8/5. 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.
Sun 8/245:05 amORD - SJU
1 stop15h 43mSpirit Airlines
Fri 8/295:42 pmSJU - ORD
1 stop17h 49mSpirit Airlines
Deal found 8/5$225
This Mytrip deal was found by Cheapflights users on 8/3. 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.
Wed 9/311:21 amORD - SJU
2 stops11h 07mSpirit Airlines
Sat 9/66:44 amSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 8/3$227
This Cheapflightsfares deal was found by Cheapflights users on 8/3. 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.
Thu 8/146:56 amORD - SJU
1 stop17h 00mSpirit Airlines
Thu 8/218:00 pmSJU - ORD
1 stop14h 22mSpirit Airlines
Deal found 8/3$228
This Mytrip deal was found by Cheapflights users on 8/5. 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 8/3011:36 amORD - SJU
2 stops26h 31mSpirit Airlines
Sat 9/66:44 amSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 8/5$229
This FlightHub deal was found by Cheapflights users on 8/5. 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.
Sat 8/3011:36 amORD - STT
2 stops25h 12mSpirit Airlines
Sat 9/610:49 amSTT - ORD
1 stop7h 50mSpirit Airlines
Deal found 8/5$230
This FlightHub deal was found by Cheapflights users on 8/5. 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.
Sat 8/236:56 amORD - SJU
1 stop16h 01mMultiple Airlines
Sat 8/303:21 pmSJU - ORD
1 stop9h 12mMultiple Airlines
Deal found 8/5$232
This Mytrip deal was found by Cheapflights users on 8/3. 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 9/611:57 amORD - SJU
2 stops25h 14mSpirit Airlines
Wed 9/103:19 pmSJU - ORD
1 stop7h 39mSpirit Airlines
Deal found 8/3$233
This FlightHub deal was found by Cheapflights users on 8/3. 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.
Sat 8/236:56 amORD - SJU
1 stop16h 01mSpirit Airlines
Sat 8/3010:10 amSJU - ORD
1 stop24h 12mSpirit Airlines
Deal found 8/3$234
This Priceline deal was found by Cheapflights users on 8/5. 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.
Tue 9/28:12 pmORD - STT
2 stops16h 36mSpirit Airlines
Tue 9/910:49 amSTT - ORD
1 stop12h 59mSpirit Airlines
Deal found 8/5$235
This FlightHub deal was found by Cheapflights users on 8/5. 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.
Fri 8/226:35 amORD - SJU
1 stop7h 50mMultiple Airlines
Mon 8/2510:16 pmSJU - ORD
1 stop12h 06mMultiple Airlines
Deal found 8/5$235
This Cheapflightsfares deal was found by Cheapflights users on 8/5. 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 9/206:15 amMDW - SJU
1 stop6h 56mFrontier
Fri 9/263:39 amSJU - MDW
1 stop7h 12mFrontier
Deal found 8/5$235

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 August 5, 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

Tue 8/12

11:28 am-2:39 am

1 stop14h 11m

San Juan Luis Munoz Marin Intl

Fri 8/15

10:16 pm-9:22 am

1 stop12h 06m

$224

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/24

5:05 am-9:48 pm

1 stop15h 43m

San Juan Luis Munoz Marin Intl

Fri 8/29

5:42 pm-10:31 am

1 stop17h 49m

$225

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 9/3

11:21 am-11:28 pm

2 stops11h 07m

San Juan Luis Munoz Marin Intl

Sat 9/6

6:44 am-4:12 pm

1 stop10h 28m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 8/14

6:56 am-12:56 am

1 stop17h 00m

San Juan Luis Munoz Marin Intl

Thu 8/21

8:00 pm-9:22 am

1 stop14h 22m

$228

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/30

11:36 am-3:07 pm

2 stops26h 31m

San Juan Luis Munoz Marin Intl

Sat 9/6

6:44 am-4:12 pm

1 stop10h 28m

$229

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 8/30

11:36 am-1:48 pm

2 stops25h 12m

Saint Thomas Island Cyril E King

Sat 9/6

10:49 am-5:39 pm

1 stop7h 50m

$230

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/23

6:56 am-11:57 pm

1 stop16h 01m

San Juan Luis Munoz Marin Intl

Sat 8/30

3:21 pm-11:33 pm

1 stop9h 12m

$232

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 9/6

11:57 am-2:11 pm

2 stops25h 14m

San Juan Luis Munoz Marin Intl

Wed 9/10

3:19 pm-9:58 pm

1 stop7h 39m

$233

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/23

6:56 am-11:57 pm

1 stop16h 01m

San Juan Luis Munoz Marin Intl

Sat 8/30

10:10 am-9:22 am

1 stop24h 12m

$234

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 9/20

6:15 am-2:11 pm

1 stop6h 56m

San Juan Luis Munoz Marin Intl

Fri 9/26

3:39 am-9:51 am

1 stop7h 12m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/5

Showing 1-10 of 60 results
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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 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 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 August 5, 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 August 5, 2025.

The most flights from USIL to zzEPX are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).

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 August 5, 2025.
Read through reviews of airlines operating flights from Illinois to Caribbean Islands, such as Southwest, Delta, and Copa Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
7,985 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
1,500 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
8,916 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
4,246 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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 Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 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 Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 9 airlines flying from Illinois to Caribbean Islands

Discover the top 9 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 August 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$359FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$382FlexibilityNo cancel feeOn-time65%
DeltaCheapest$190Average$613FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$193Average$476FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$194Average$667FlexibilityNo 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$748FlexibilityNo cancel feeOn-time67%

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