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$114+ Cheap flights from Illinois to Caribbean

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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Jun 20 — Jun 271
Fr 6/20
Fr 6/27
1 adult, Economy
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Cheap flight deals from Illinois to Caribbean

Keep the following information in mind while searching for Illinois to Caribbean flight deals. Data was last updated Juni 15, 2025.

Round-trip from

$215
(Priceline)

One-way from

$114
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$413

Good round-trip deal

$298 or less

Good one-way deal

$150 or less
From Illinois to Caribbean
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One-way flight from Illinois to Caribbean
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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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Price to beat on a round-trip flight from Illinois to Caribbean.
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Price to beat on a one-way flight from Illinois to Caribbean.
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Find flight deals from Illinois to Caribbean

Cheapest flights from Illinois to Caribbean
Explore the most affordable flight options available from Illinois to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on Juni 15, 2025.

This Priceline deal was found by Cheapflights users on 6/13. 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.
Sa 7/1212:20 pmORD - SJU
1 stop11h 07mMultiple Airlines
Di 7/154:43 pmSJU - ORD
1 stop15h 21mMultiple Airlines
Deal found 6/13$215
This FlightHub deal was found by Cheapflights users on 6/13. 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.
Mo 9/295:10 amORD - SJU
1 stop8h 05mFrontier
Sa 10/43:21 pmSJU - ORD
1 stop9h 00mFrontier
Deal found 6/13$216
This eDestinos deal was found by Cheapflights users on 6/14. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 7/110:46 amORD - SJU
1 stop13h 45mSpirit Airlines
Di 7/154:43 pmSJU - ORD
1 stop15h 21mSpirit Airlines
Deal found 6/14$217
This Priceline deal was found by Cheapflights users on 6/14. 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.
So 6/299:12 pmMDW - SJU
1 stop28h 23mFrontier
Fr 7/43:34 amSJU - MDW
1 stop17h 48mFrontier
Deal found 6/14$221
This FlightHub deal was found by Cheapflights users on 6/13. 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.
Di 7/87:49 pmORD - STT
1 stop15h 41mSpirit Airlines
Sa 7/124:05 pmSTT - ORD
1 stop8h 22mSpirit Airlines
Deal found 6/13$269
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Di 8/128:34 pmORD - PUJ
1 stop15h 31mAmerican Airlines
Di 8/192:20 pmPUJ - ORD
1 stop9h 39mAmerican Airlines
Deal found 6/14$295
This Cheapflightsfares deal was found by Cheapflights users on 6/13. 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.
Di 8/195:05 amORD - PUJ
1 stop8h 25mSpirit Airlines
Sa 8/233:35 pmPUJ - ORD
1 stop9h 24mSpirit Airlines
Deal found 6/13$297
This Travelocity deal was found by Cheapflights users on 6/14. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 12/610:27 amORD - PUJ
Nonstop4h 45mArajet
Sa 12/135:47 amPUJ - ORD
Nonstop5h 10mArajet
Deal found 6/14$302
This Vliegwinkel deal was found by Cheapflights users on 6/13. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 7/148:45 pmORD - PUJ
1 stop13h 16mFinnair
Di 7/224:10 pmPUJ - ORD
2 stops19h 27mFinnair
Deal found 6/13$303
This United Airlines deal was found by Cheapflights users on 6/13. 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.
So 11/166:00 amORD - PUJ
1 stop9h 25mUnited Airlines
Do 11/202:55 pmPUJ - ORD
Nonstop5h 13mUnited Airlines
Deal found 6/13$305
This Orbitz deal was found by Cheapflights users on 6/13. 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.
Mi 11/125:05 amORD - PUJ
1 stop8h 29mMultiple Airlines
So 11/166:00 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Deal found 6/13$313
This United Airlines deal was found by Cheapflights users on 6/14. 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.
Sa 6/286:03 pmORD - SJU
Nonstop4h 51mUnited Airlines
Fr 10/33:56 pmSJU - ORD
Nonstop5h 07mUnited Airlines
Deal found 6/14$320

Cheapflights Fare Finder

Customize your flight search to find flights from Illinois to Caribbean 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 Juni 15, 2025.
Use the filters below to find and compare flights from Illinois to Caribbean that are best for you.

Fly from

Illinois

Fly to

Caribbean

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sa 7/12

12:20 pm-12:27 am

1 stop11h 07m

San Juan Luis Munoz Marin Intl

Di 7/15

4:43 pm-7:04 am

1 stop15h 21m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mo 9/29

5:10 am-2:15 pm

1 stop8h 05m

San Juan Luis Munoz Marin Intl

Sa 10/4

3:21 pm-11:21 pm

1 stop9h 00m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Di 7/1

10:46 am-1:31 am

1 stop13h 45m

San Juan Luis Munoz Marin Intl

Di 7/15

4:43 pm-7:04 am

1 stop15h 21m

$217

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

So 6/29

9:12 pm-2:35 am

1 stop28h 23m

San Juan Luis Munoz Marin Intl

Fr 7/4

3:34 am-8:22 pm

1 stop17h 48m

$221

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Di 7/8

7:49 pm-12:30 pm

1 stop15h 41m

Saint Thomas Island Cyril E King

Sa 7/12

4:05 pm-11:27 pm

1 stop8h 22m

$269

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Di 8/12

8:34 pm-1:05 pm

1 stop15h 31m

Punta Cana

Di 8/19

2:20 pm-10:59 pm

1 stop9h 39m

$295

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Di 8/19

5:05 am-2:30 pm

1 stop8h 25m

Punta Cana

Sa 8/23

3:35 pm-11:59 pm

1 stop9h 24m

$297

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sa 12/6

10:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sa 12/13

5:47 am-8:57 am

Nonstop5h 10m

$302

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mo 7/14

8:45 pm-11:01 am

1 stop13h 16m

Punta Cana

Di 7/22

4:10 pm-10:37 am

2 stops19h 27m

$303

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

So 11/16

6:00 am-5:25 pm

1 stop9h 25m

Punta Cana

Do 11/20

2:55 pm-6:08 pm

Nonstop5h 13m

$305

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/13

Showing 1-10 of 60 results
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Best time to book a flight from Illinois to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

What is the cheapest month to book a flight from Illinois to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Illinois to Caribbean (average of $254). Flying from Illinois to Caribbean 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 CB?

Find hourly flight availability from Illinois to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated Juni 15, 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 as you normally would.

Weekly flight availability from Illinois to Caribbean

Explore weekly flight availability from Illinois to Caribbean. 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 Juni 15, 2025.

The most flights from USIL to 0CB 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 by month

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

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated Juni 15, 2025.
Delta
8.0
Very good
7,958 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Boarding

8.2

Crew

8.5

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
7,958 reviews
Delta
8.0
Very good
7,958 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Boarding

8.2

Crew

8.5

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
4,285 reviews
Delta
8.0
Very good
7,958 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Boarding

8.2

Crew

8.5

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!
Finnair
7.6
Good
1,290 reviews
Delta
8.0
Very good
7,958 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Boarding

8.2

Crew

8.5

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
1,451 reviews
Delta
8.0
Very good
7,958 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Boarding

8.2

Crew

8.5

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
8,793 reviews
Delta
8.0
Very good
7,958 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Boarding

8.2

Crew

8.5

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. 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 one-way?

    The cheapest airlines for a one-way flight from Illinois to Caribbean are Frontier ($114), Spirit Airlines ($117), and Southwest ($121).

  • Can I find deals for flights from Illinois to Caribbean that include hotel bookings?

    Yes. In addition to deals on Illinois to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Caribbean.

  • Can I find deals for business class flights from Illinois to Caribbean?

    Yes. Cheapflights offers flight deals from Illinois to Caribbean 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?

    Currently, September is the cheapest month in which you can book a flight from Illinois to Caribbean (average of $254). Flying from Illinois to Caribbean 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

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to LaGuardia flights
Los Angeles to John F Kennedy Intl flights
John F Kennedy Intl to O'Hare Intl flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to Cancún flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
Los Angeles to Seattle flights
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Miami flights
Newark to Miami flights
Newark to Cancún flights
Los Angeles to Newark flights
Dallas/Fort Worth to Seattle flights
Dallas/Fort Worth to O'Hare Intl flights
Los Angeles to Haneda flights
John F Kennedy Intl to Seattle flights
John F Kennedy Intl to Las Vegas flights
Newark to O'Hare Intl flights
John F Kennedy Intl to San Francisco flights
LaGuardia to Fort Lauderdale flights
Dallas/Fort Worth to John F Kennedy Intl flights
John F Kennedy Intl to Heathrow flights
Newark to Los Angeles flights
Newark to Seattle flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Charles de Gaulle flights
Los Angeles to Honolulu flights
LaGuardia to O'Hare Intl flights
Dallas/Fort Worth to Newark flights
Newark to Las Vegas flights
Dallas/Fort Worth to Cancún flights
Los Angeles to O'Hare Intl flights
O'Hare Intl to John F Kennedy Intl flights
LaGuardia to Miami flights
San Francisco to John F Kennedy Intl flights
George Bush Intcntl to Cancún flights
Seattle to Los Angeles flights
John F Kennedy Intl to Santiago de los Caballeros flights
Dallas/Fort Worth to Las Vegas flights
Atlanta to John F Kennedy Intl flights
O'Hare Intl to Cancún flights
Los Angeles to Narita flights
Newark to Orlando flights
LaGuardia to Dallas/Fort Worth flights
San Francisco to Newark flights
John F Kennedy Intl to Atlanta flights
John F Kennedy Intl to Leonardo da Vinci/Fiumicino flights
Newark to Charles de Gaulle flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Haneda flights

Top 10 airlines flying from Illinois to Caribbean

Discover the top 10 airlines that operate flights from Illinois to Caribbean. 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 Juni 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$374FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$140Average$361FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$193Average$538FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$194Average$670FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$202Average$483FlexibilityNo cancel feeOn-time62%
DeltaCheapest$216Average$621FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$226Average$674FlexibilityNo cancel feeOn-time69%
ArajetCheapest$240Average$330FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$335Average$751FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$354Average$654FlexibilityNo cancel feeOn-time63%

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