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Caribbean Islands

$92+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Oct 25 — Nov 11
Sat 10/25
Sat 11/1
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 September 25, 2025.

Round-trip from

$196
(Cheapflightsfares)

One-way from

$92
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$380
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. 8% potential increase in price ($36 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 September 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 September 25, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 10/319:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Mon 11/38:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 9/23$196
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/179:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 9/23$199
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/209:06 pmORD - SJU
Nonstop4h 45mMultiple Airlines
Sun 10/269:19 pmSJU - ORD
1 stop10h 51mMultiple Airlines
Deal found 9/23$200
This CheapOair deal was found by Cheapflights users on 9/23. 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.
Sat 10/253:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Sun 11/212:51 pmSJU - ORD
1 stop7h 47mSpirit Airlines
Deal found 9/23$201
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/209:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Tue 10/283:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/23$202
This Mytrip deal was found by Cheapflights users on 9/24. 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.
Fri 10/249:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Fri 10/315:18 pmSJU - ORD
2 stops27h 32mSpirit Airlines
Deal found 9/24$203
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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.
Sat 10/256:58 pmORD - STT
1 stop17h 37mSpirit Airlines
Sat 11/12:01 pmSTT - ORD
1 stop8h 32mSpirit Airlines
Deal found 9/23$205
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/12:03 pmORD - SJU
Nonstop4h 39mSpirit Airlines
Wed 11/192:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 9/24$205
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/227:43 pmORD - SJU
1 stop14h 13mMultiple Airlines
Thu 10/239:06 pmSJU - ORD
1 stop13h 16mMultiple Airlines
Deal found 9/24$206
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/209:06 pmORD - SJU
Nonstop4h 45mMultiple Airlines
Fri 10/241:59 amSJU - ORD
1 stop19h 49mMultiple Airlines
Deal found 9/24$207
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/227:43 pmORD - SJU
1 stop14h 13mSpirit Airlines
Wed 10/293:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/24$208
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/156:40 amORD - SJU
1 stop18h 22mMultiple Airlines
Sat 10/253:19 pmSJU - ORD
1 stop7h 14mMultiple Airlines
Deal found 9/23$209

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 September 25, 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

MDW - SJU

MDWSJU

Chicago Midway

Thu 10/30

6:35 am-4:40 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Tue 11/4

11:20 am-7:35 pm

2 stops10h 15m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 10/30

1:00 pm-9:22 pm

1 stop7h 22m

San Juan Luis Munoz Marin Intl

Mon 11/3

2:05 am-9:05 am

1 stop9h 00m

$276

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 10/22

3:10 pm-11:50 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Wed 10/29

2:45 pm-10:45 pm

1 stop9h 00m

$311

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 10/31

8:55 am-2:40 pm

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Mon 11/10

2:05 am-9:05 am

1 stop9h 00m

$313

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 11/12

10:35 am-11:56 pm

1 stop11h 21m

San Juan Luis Munoz Marin Intl

Tue 11/18

7:15 am-5:53 pm

1 stop12h 38m

$319

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 11/3

9:30 am-4:02 pm

Nonstop4h 32m

Punta Cana

Sat 11/8

4:25 pm-7:38 pm

Nonstop5h 13m

$328

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 11/10

6:00 am-3:38 pm

1 stop7h 38m

Punta Cana

Sat 11/15

3:40 pm-9:01 am

1 stop19h 21m

$337

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 11/10

5:23 am-3:38 pm

1 stop8h 15m

Punta Cana

Fri 11/14

2:38 pm-12:01 am

1 stop11h 23m

$337

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Thu 11/13

8:02 pm-1:13 pm

1 stop15h 11m

Punta Cana

Sat 11/15

2:57 pm-8:42 am

2 stops19h 45m

$342

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 10/28

9:30 am-3:02 pm

Nonstop4h 32m

Punta Cana

Tue 11/4

2:55 pm-6:08 pm

Nonstop5h 13m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/25

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 September 25, 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 September 25, 2025.

The most flights from USIL to zzEPX are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 7h 22m. 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 Frontier, which is currently one of the cheapest options available, starting at $99. Arajet flights start at $104 while deals on United Airlines start at $109 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 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

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 September 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$377FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$372FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$194Average$664FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$621FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$226Average$651FlexibilityNo cancel feeOn-time69%
ArajetCheapest$232Average$318FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$261Average$477FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$335Average$647FlexibilityNo cancel feeOn-time67%

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