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Caribbean Islands

$87+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
1 adult, Economy
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Cheap 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 February 11, 2026.

This Spirit deal was found by Cheapflights users on 2/10. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2012:18 pm
ORD
-
SJU
Nonstop4h 36m
Spirit Airlines
Thu 4/2312:30 pm
SJU
-
ORD
Nonstop5h 08m
Spirit Airlines
Deal found 2/10$179
This Cheapflightsfares deal was found by Cheapflights users on 2/10. 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 3/28:16 pm
ORD
-
SJU
1 stop17h 15m
Spirit Airlines
Fri 3/611:52 am
SJU
-
ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/10$181
This Cheapflightsfares deal was found by Cheapflights users on 2/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2312:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Fri 2/275:45 pm
SJU
-
ORD
1 stop8h 55m
Spirit Airlines
Deal found 2/8$182
This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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 3/28:16 pm
ORD
-
SJU
1 stop17h 15m
Spirit Airlines
Thu 3/512:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/11$183
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Sat 5/91:27 pm
ORD
-
SJU
1 stop22h 06m
Frontier
Fri 5/156:00 am
SJU
-
ORD
1 stop17h 57m
Frontier
Deal found 2/10$184
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Tue 2/2412:17 pm
ORD
-
SJU
Nonstop4h 32m
Multiple Airlines
Mon 3/93:22 pm
SJU
-
ORD
1 stop8h 17m
Multiple Airlines
Deal found 2/10$185
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Tue 2/2412:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Tue 3/106:00 am
SJU
-
ORD
1 stop12h 03m
Spirit Airlines
Deal found 2/10$186
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Mon 2/2312:17 pm
ORD
-
SJU
Nonstop4h 32m
Multiple Airlines
Wed 2/254:06 pm
SJU
-
ORD
2 stops32h 59m
Multiple Airlines
Deal found 2/11$187
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Wed 2/2512:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Fri 3/612:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/10$188
This CheapOair deal was found by Cheapflights users on 2/7. 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.
Mon 3/29:22 pm
MDW
-
SJU
1 stop25h 21m
Frontier
Wed 3/45:25 pm
SJU
-
MDW
1 stop23h 01m
Frontier
Deal found 2/7$188
This Priceline deal was found by Cheapflights users on 2/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/233:49 pm
STL
-
SJU
1 stop6h 54m
Frontier
Wed 3/45:25 pm
SJU
-
STL
1 stop7h 02m
Frontier
Deal found 2/9$188
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Wed 3/48:30 am
ORD
-
SJU
1 stop16h 23m
Multiple Airlines
Fri 3/611:52 am
SJU
-
ORD
1 stop8h 26m
Multiple Airlines
Deal found 2/9$189

Find 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 February 11, 2026.

Round-trip from

$179
(Spirit)

One-way from

$87
(CheapOair)

Popular in

December

Cheapest in

April

Average price

$387
From Illinois to Caribbean Islands
Search Deals
One-way flight from Illinois to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 11, 2026.
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

MDW - SJU

MDWSJU

Chicago Midway

Wed 5/13

12:51 pm-10:17 pm

1 stop8h 26m

San Juan Luis Munoz Marin Intl

Mon 5/18

12:50 pm-9:09 pm

1 stop9h 19m

$246

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sun 5/3

11:43 am-11:13 pm

1 stop10h 30m

San Juan Luis Munoz Marin Intl

Sun 5/10

5:15 pm-11:59 pm

1 stop7h 44m

$246

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 5/13

2:59 pm-10:17 pm

1 stop6h 18m

San Juan Luis Munoz Marin Intl

Sun 5/24

12:50 pm-11:59 pm

1 stop12h 09m

$256

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 5/13

9:44 am-10:17 pm

1 stop11h 33m

San Juan Luis Munoz Marin Intl

Sat 5/23

7:00 am-5:35 pm

1 stop11h 35m

$256

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/5

8:15 am-4:23 pm

1 stop7h 08m

San Juan Luis Munoz Marin Intl

Thu 5/14

5:15 pm-11:59 pm

1 stop7h 44m

$256

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 5/6

7:14 am-4:23 pm

1 stop8h 09m

San Juan Luis Munoz Marin Intl

Wed 5/13

2:20 pm-8:25 pm

1 stop7h 05m

$256

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/12

6:41 am-4:23 pm

1 stop8h 42m

San Juan Luis Munoz Marin Intl

Wed 5/13

5:15 pm-11:59 pm

1 stop7h 44m

$256

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 5/10

9:44 am-10:17 pm

1 stop11h 33m

San Juan Luis Munoz Marin Intl

Wed 5/13

2:20 pm-8:25 pm

1 stop7h 05m

$256

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 2/24

8:25 am-5:05 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Thu 2/26

5:30 am-1:50 pm

2 stops10h 20m

$286

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 5/9

5:40 am-1:20 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Wed 5/13

5:35 am-1:25 pm

2 stops8h 50m

$286

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

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, April is the cheapest month in which you can book a flight from Illinois to Caribbean Islands (average of $91). Flying from Illinois to Caribbean Islands in December is currently the most expensive (average of $195). 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 February 11, 2026.

It’s optimal to fly from Illinois to Caribbean Islands in the evening. By choosing this option you can save up to 41% 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 February 7, 2026.

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 at noon 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 February 11, 2026.

The most flights from USIL to zzEPX are scheduled on a Monday (11 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 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 6h 40m. Illinois and Caribbean Islands are separated by a distance of 2057 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 JetBlue, which is currently one of the cheapest options available, starting at $67. Spirit Airlines flights start at $72 while deals on Frontier start at $74 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, April is the cheapest month in which you can book a flight from Illinois to Caribbean Islands (average of $91). Flying from Illinois to Caribbean Islands in December is currently the most expensive (average of $195). 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 February 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$450FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$119Average$444FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$130Average$354FlexibilityNo cancel feeOn-time65%
DeltaCheapest$132Average$578FlexibilityNo cancel feeOn-timeN/A
ArajetCheapest$180Average$321FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$193Average$576FlexibilityNo cancel feeOn-time67%
Hahn AirCheapest$213Average$343FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$225Average$631FlexibilityNo cancel feeOn-time71%

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