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Caribbean Islands

$115+ 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
jun. 23 — jun. 301
lun. 6/23
lun. 6/30
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 junio 18, 2025.

Round-trip from

$212
(Priceline)

One-way from

$115
(Frontier)

Popular in

December

Cheapest in

September

Average price

$413
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 ($54 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 June 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 junio 18, 2025.

This Priceline deal was found by Cheapflights users on 6/17. 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.
mar. 6/2411:28 amORD - SJU
1 stop14h 07mFrontier
lun. 6/305:40 amSJU - ORD
1 stop29h 37mFrontier
Deal found 6/17$212
This FlightHub deal was found by Cheapflights users on 6/17. 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.
mar. 7/810:43 amORD - SJU
1 stop12h 22mSpirit Airlines
mar. 7/154:43 pmSJU - ORD
1 stop15h 21mSpirit Airlines
Deal found 6/17$215
This FlightHub deal was found by Cheapflights users on 6/16. 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.
vie. 7/1111:15 amORD - SJU
1 stop12h 31mMultiple Airlines
mar. 7/154:43 pmSJU - ORD
1 stop15h 21mMultiple Airlines
Deal found 6/16$219
This Priceline deal was found by Cheapflights users on 6/16. 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.
dom. 6/299:12 pmMDW - SJU
1 stop26h 16mFrontier
vie. 7/43:15 pmSJU - MDW
1 stop9h 03mFrontier
Deal found 6/16$221
This Booking.com deal was found by Cheapflights users on 6/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/87:49 pmORD - STT
1 stop15h 41mSpirit Airlines
mar. 7/224:05 pmSTT - ORD
1 stop8h 06mSpirit Airlines
Deal found 6/17$255
This American Airlines deal was found by Cheapflights users on 6/16. 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.
lun. 8/187:05 pmORD - PUJ
1 stop14h 50mAmerican Airlines
jue. 8/2111:55 amPUJ - ORD
1 stop8h 49mAmerican Airlines
Deal found 6/16$295
This Orbitz deal was found by Cheapflights users on 6/17. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/24:35 amORD - PUJ
Nonstop4h 45mArajet
dom. 12/76:00 pmPUJ - ORD
Nonstop5h 10mArajet
Deal found 6/17$302
This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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.
mar. 7/295:05 amORD - PUJ
1 stop8h 25mSpirit Airlines
jue. 7/313:25 pmPUJ - ORD
1 stop9h 28mSpirit Airlines
Deal found 6/16$306
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
mar. 7/11:43 pmORD - PUJ
1 stop29h 11mMultiple Airlines
sáb. 2/75:47 amPUJ - ORD
Nonstop5h 10mMultiple Airlines
Deal found 6/17$312
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/226:35 amMDW - PUJ
1 stop6h 20mSouthwest
vie. 9/263:05 pmPUJ - MDW
1 stop7h 55mSouthwest
Deal found 6/16$315
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 7/75:15 pmMDW - SJU
1 stop6h 40mSouthwest
vie. 7/1111:25 amSJU - MDW
2 stops8h 55mSouthwest
Deal found 6/16$327
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/89:23 amORD - PUJ
Nonstop4h 42mUnited Airlines
mar. 8/124:35 pmPUJ - ORD
1 stop7h 55mUnited Airlines
Deal found 6/17$335

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 junio 18, 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

mar. 6/24

11:28 am-2:35 am

1 stop14h 07m

San Juan Luis Munoz Marin Intl

lun. 6/30

5:40 am-10:17 am

1 stop29h 37m

$212

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 7/8

10:43 am-12:05 am

1 stop12h 22m

San Juan Luis Munoz Marin Intl

mar. 7/15

4:43 pm-7:04 am

1 stop15h 21m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

vie. 7/11

11:15 am-12:46 am

1 stop12h 31m

San Juan Luis Munoz Marin Intl

sáb. 7/19

4:30 pm-7:04 am

1 stop15h 34m

$217

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

dom. 6/29

9:12 pm-12:28 am

1 stop26h 16m

San Juan Luis Munoz Marin Intl

vie. 7/4

10:59 am-11:51 pm

1 stop13h 52m

$221

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

mar. 7/8

7:49 pm-12:30 pm

1 stop15h 41m

Saint Thomas Island Cyril E King

mar. 7/22

4:05 pm-11:11 pm

1 stop8h 06m

$255

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

lun. 8/18

7:05 pm-10:55 am

1 stop14h 50m

Punta Cana

jue. 8/21

11:55 am-7:44 pm

1 stop8h 49m

$295

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 7/29

5:05 am-2:30 pm

1 stop8h 25m

Punta Cana

jue. 7/31

3:25 pm-11:53 pm

1 stop9h 28m

$306

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 7/1

1:43 pm-7:54 pm

1 stop29h 11m

Punta Cana

sáb. 2/7

5:47 am-8:57 am

Nonstop5h 10m

$312

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

lun. 9/22

6:35 am-1:55 pm

1 stop6h 20m

Punta Cana

vie. 9/26

3:05 pm-10:00 pm

1 stop7h 55m

$315

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

lun. 7/7

5:15 pm-12:55 am

1 stop6h 40m

San Juan Luis Munoz Marin Intl

vie. 7/11

11:25 am-7:20 pm

2 stops8h 55m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

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 junio 18, 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 junio 18, 2025.

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

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 junio 18, 2025.
Read through reviews of airlines operating flights from Illinois to Caribbean Islands, such as Delta, Southwest and Air Transat. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,964 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Southwest
8.0
Very good
4,280 reviews
Delta
8.0
Very good
7,964 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Transat
7.8
Good
398 reviews
Delta
8.0
Very good
7,964 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Copa Airlines
7.5
Good
1,455 reviews
Delta
8.0
Very good
7,964 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,810 reviews
Delta
8.0
Very good
7,964 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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 $115. American Airlines flights start at $121 while deals on Southwest start at $121 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

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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 10 airlines flying from Illinois to Caribbean Islands

Discover the top 10 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 junio 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$364FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$140Average$364FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$193Average$537FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$194Average$669FlexibilityNo cancel feeOn-time71%
DeltaCheapest$216Average$618FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$226Average$674FlexibilityNo cancel feeOn-time69%
ArajetCheapest$240Average$330FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$261Average$496FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$335Average$751FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$354Average$653FlexibilityNo cancel feeOn-time63%

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