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Caribbean Islands

$72+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Feb 1 — Feb 81
Sun 2/1
Sun 2/8
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 January 2, 2026.

This Kiwi.com deal was found by Cheapflights users on 12/31. 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 12/316:05 pmORD - SJU
1 stop23h 08mMultiple Airlines
Tue 1/139:00 amSJU - ORD
1 stop9h 52mMultiple Airlines
Deal found 12/31$330
This Mytrip deal was found by Cheapflights users on 12/31. 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 12/317:10 amORD - PUJ
Nonstop4h 37mMultiple Airlines
Wed 1/74:55 pmPUJ - ORD
1 stop27h 56mMultiple Airlines
Deal found 12/31$337
This Kiwi.com deal was found by Cheapflights users on 12/31. 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 12/316:05 pmORD - SJU
1 stop23h 08mSpirit Airlines
Tue 1/131:22 pmSJU - ORD
Nonstop5h 15mSpirit Airlines
Deal found 12/31$346
This Kiwi.com deal was found by Cheapflights users on 12/31. 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 12/316:05 pmORD - SJU
1 stop23h 08mMultiple Airlines
Wed 1/79:19 pmSJU - ORD
1 stop20h 09mMultiple Airlines
Deal found 12/31$371
This CheapOair deal was found by Cheapflights users on 12/31. 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 12/3112:39 pmORD - SJU
1 stop9h 15mFrontier
Thu 1/86:30 amSJU - ORD
1 stop10h 58mFrontier
Deal found 12/31$374
This CheapOair deal was found by Cheapflights users on 12/31. 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 12/318:15 amMDW - SJU
1 stop13h 39mFrontier
Tue 1/134:35 pmSJU - MDW
1 stop7h 44mFrontier
Deal found 12/31$374
This Kiwi.com deal was found by Cheapflights users on 12/30. 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 12/317:10 amORD - SJU
1 stop7h 34mMultiple Airlines
Wed 12/318:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Deal found 12/30$435
This Kiwi.com deal was found by Cheapflights users on 12/31. 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 12/317:10 amORD - PUJ
Nonstop4h 37mFrontier
Wed 1/72:32 pmPUJ - ORD
2 stops34h 07mFrontier
Deal found 12/31$442
This CheapOair deal was found by Cheapflights users on 12/31. 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 12/316:00 pmORD - PUJ
2 stops25h 45mAir Canada
Tue 1/611:00 pmPUJ - ORD
2 stops21h 50mAir Canada
Deal found 12/31$444
This Priceline deal was found by Cheapflights users on 12/30. 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 12/316:45 amORD - SJU
1 stop10h 04mMultiple Airlines
Thu 1/14:21 pmSJU - ORD
1 stop8h 03mMultiple Airlines
Deal found 12/30$453
This FlightHub deal was found by Cheapflights users on 12/31. 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 12/3110:35 amORD - PUJ
1 stop25h 25mAir Canada
Wed 1/74:55 pmPUJ - ORD
1 stop29h 15mAir Canada
Deal found 12/31$458
This Kiwi.com deal was found by Cheapflights users on 12/30. 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 12/317:10 amORD - SJU
1 stop7h 34mFrontier
Thu 1/14:21 pmSJU - ORD
1 stop8h 03mFrontier
Deal found 12/30$484

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 January 2, 2026.

Round-trip from

$192
(CheapOair)

One-way from

$72
(Priceline)

Popular in

December

Cheapest in

April

Average price

$343
From Illinois to Caribbean Islands
Search Deals
One-way flight from Illinois to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 2, 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

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 3/19

6:44 am-5:23 pm

1 stop9h 39m

San Juan Luis Munoz Marin Intl

Tue 3/24

3:26 am-11:25 am

1 stop8h 59m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/24

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Sun 2/1

9:25 am-6:32 pm

1 stop11h 07m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/25

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Sun 2/1

9:25 am-6:32 pm

1 stop11h 07m

$197

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 1/9

7:45 am-6:07 pm

1 stop8h 22m

San Juan Luis Munoz Marin Intl

Thu 1/15

11:06 am-7:36 pm

1 stop10h 30m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

10:15 am-7:26 pm

1 stop7h 11m

San Juan Luis Munoz Marin Intl

Sat 1/24

10:25 am-7:36 pm

1 stop11h 11m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 3/19

6:44 am-5:23 pm

1 stop9h 39m

San Juan Luis Munoz Marin Intl

Wed 3/25

1:30 am-10:05 am

1 stop9h 35m

$206

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/5

6:45 am-4:26 pm

1 stop7h 41m

San Juan Luis Munoz Marin Intl

Wed 1/14

11:06 am-7:36 pm

1 stop10h 30m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/28

12:59 pm-12:29 am

1 stop9h 30m

San Juan Luis Munoz Marin Intl

Fri 3/13

1:30 am-10:05 am

1 stop9h 35m

$220

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 1/17

5:15 am-4:36 pm

1 stop9h 21m

Punta Cana

Sat 1/24

5:47 pm-11:46 pm

1 stop7h 59m

$258

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 2/3

7:20 am-4:37 pm

1 stop7h 17m

Saint Thomas Island Cyril E King

Wed 2/11

3:57 pm-9:44 pm

1 stop7h 47m

$280

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/31

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 $127). Flying from Illinois to Caribbean Islands in December is currently the most expensive (average of $221). 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 January 2, 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 December 27, 2025.

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 January 2, 2026.

The most flights from USIL to zzEPX are scheduled on a Monday (12 on average). You will have fewer flight options on Tuesday, 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 9h 05m. 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 $54. Frontier flights start at $65 while deals on Spirit Airlines start at $92 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 $127). Flying from Illinois to Caribbean Islands in December is currently the most expensive (average of $221). 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 January 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$115Average$450FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$136Average$449FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$375FlexibilityNo cancel feeOn-time65%
DeltaCheapest$186Average$593FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
ArajetCheapest$199Average$335FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$623FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$225Average$640FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$277Average$639FlexibilityNo cancel feeOn-time63%

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