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Caribbean Islands

$78+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Dec 10 — Dec 171
Wed 12/10
Wed 12/17
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 November 10, 2025.

Round-trip from

$213
(Kiwi.com)

One-way from

$78
(Super.com)

Popular in

December

Cheapest in

April

Average price

$432
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. 11% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 10, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/8. 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 12/612:09 pmORD - SJU
1 stop6h 30mMultiple Airlines
Thu 12/114:31 pmSJU - ORD
1 stop7h 53mMultiple Airlines
Deal found 11/8$213
This Priceline deal was found by Cheapflights users on 11/8. 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.
Fri 12/52:00 pmORD - SJU
1 stop8h 49mMultiple Airlines
Mon 12/84:10 amSJU - ORD
2 stops11h 48mMultiple Airlines
Deal found 11/8$214
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 12/107:41 pmORD - SJU
1 stop11h 56mMultiple Airlines
Thu 12/114:31 pmSJU - ORD
1 stop7h 53mMultiple Airlines
Deal found 11/8$215
This Super.com deal was found by Cheapflights users on 11/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:40 amORD - SJU
Nonstop4h 41mSpirit Airlines
Thu 12/118:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 11/9$216
This CheapOair deal was found by Cheapflights users on 11/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:16 pmMDW - SJU
1 stop18h 16mFrontier
Thu 12/184:21 pmSJU - MDW
1 stop7h 51mFrontier
Deal found 11/10$216
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Fri 12/52:00 pmORD - SJU
1 stop8h 49mMultiple Airlines
Wed 12/107:10 amSJU - ORD
2 stops14h 51mMultiple Airlines
Deal found 11/10$217
This CheapOair deal was found by Cheapflights users on 11/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:40 amORD - SJU
Nonstop4h 42mSpirit Airlines
Mon 12/158:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 11/10$218
This Kiwi.com deal was found by Cheapflights users on 11/8. 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.
Fri 12/52:00 pmORD - SJU
1 stop8h 49mMultiple Airlines
Mon 12/1510:42 amSJU - ORD
1 stop9h 54mMultiple Airlines
Deal found 11/8$219
This Cheapflightsfares deal was found by Cheapflights users on 11/10. 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 11/245:00 amORD - SJU
1 stop13h 27mSpirit Airlines
Thu 11/2711:55 amSJU - ORD
1 stop13h 18mSpirit Airlines
Deal found 11/10$220
This American Airlines deal was found by Cheapflights users on 11/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:26 pmORD - SJU
1 stop12h 09mAmerican Airlines
Thu 1/154:28 pmSJU - ORD
Nonstop5h 32mAmerican Airlines
Deal found 11/10$221
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:44 amMDW - SJU
1 stop30h 29mFrontier
Sat 12/131:59 amSJU - MDW
2 stops35h 09mFrontier
Deal found 11/9$221
This Trip.com deal was found by Cheapflights users on 11/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:00 amORD - SJU
1 stop12h 08mMultiple Airlines
Sun 12/146:00 amSJU - ORD
1 stop16h 09mMultiple Airlines
Deal found 11/9$222

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 November 10, 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

Sun 1/4

5:30 am-5:30 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Sat 1/17

6:15 am-1:40 pm

1 stop9h 25m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/19

10:46 am-11:44 pm

1 stop10h 58m

San Juan Luis Munoz Marin Intl

Fri 1/23

7:30 am-12:01 pm

1 stop6h 31m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/24

10:46 am-11:44 pm

1 stop10h 58m

San Juan Luis Munoz Marin Intl

Tue 1/27

3:55 pm-10:26 pm

1 stop8h 31m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/20

12:48 pm-11:44 pm

1 stop8h 56m

San Juan Luis Munoz Marin Intl

Tue 1/27

3:55 pm-10:26 pm

1 stop8h 31m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/29

3:15 pm-12:35 am

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Tue 2/3

9:05 am-2:45 pm

1 stop7h 40m

$226

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 1/29

10:24 am-11:59 pm

1 stop11h 35m

San Juan Luis Munoz Marin Intl

Wed 2/4

7:00 am-1:14 pm

1 stop8h 14m

$226

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/31

12:15 pm-11:00 pm

1 stop8h 45m

San Juan Luis Munoz Marin Intl

Tue 2/3

6:10 am-1:55 pm

2 stops9h 45m

$246

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 2/3

2:20 pm-12:35 am

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Fri 2/6

4:10 pm-10:25 pm

1 stop8h 15m

$252

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/8

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Tue 2/10

2:05 am-10:53 am

1 stop10h 48m

$254

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

3:45 pm-12:40 am

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:10 am-9:50 pm

2 stops17h 40m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

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, January is the cheapest month in which you can book a flight from Illinois to Caribbean Islands (average of $126). Flying from Illinois to Caribbean Islands in December is currently the most expensive (average of $188). 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 November 10, 2025.

It’s optimal to fly from Illinois to Caribbean Islands in the evening. By choosing this option you can save up to 31% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Illinois to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Illinois to Caribbean Islands. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Illinois to Caribbean Islands flight should consider departing on Tuesday mornings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 10, 2025.

The most flights from USIL to zzEPX are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).

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.

  • How long is the flight from Illinois to Caribbean Islands?

    Departing from Illinois to Caribbean Islands will take you 4h 40m. Illinois and Caribbean Islands are separated by a distance of 2073 mi. This flight may include one or multiple stops.

  • 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 $97. Delta flights start at $113 while deals on Southwest start at $113 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, January is the cheapest month in which you can book a flight from Illinois to Caribbean Islands (average of $126). Flying from Illinois to Caribbean Islands in December is currently the most expensive (average of $188). 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 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 November 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$451FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$376FlexibilityNo cancel feeOn-time65%
DeltaCheapest$186Average$627FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$225Average$656FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$226Average$641FlexibilityNo cancel feeOn-time69%
ArajetCheapest$233Average$330FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$261Average$484FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$335Average$612FlexibilityNo cancel feeOn-time67%

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