HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$90+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to Caribbean with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 1, 2025.

Round-trip from

$180
(eDestinos)

One-way from

$90
(eDestinos)

Popular in

December

Cheapest in

August

Average price

$312

Good round-trip deal

$297 or less

Good one-way deal

$175 or less
From Illinois to Caribbean
Search Deals
One-way flight from Illinois to Caribbean
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($69 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Illinois to Caribbean.
Search Deals
Price to beat on a one-way flight from Illinois to Caribbean.
Search Deals

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 April 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/138:45 amORD - SJU
1 stop14h 01mSpirit Airlines
Wed 4/306:35 amSJU - ORD
Nonstop5h 23mSpirit Airlines
Deal found 3/30$182
This FlightHub deal was found by Cheapflights users on 3/31. 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.
Tue 4/157:00 pmORD - SJU
1 stop12h 26mMultiple Airlines
Sun 4/205:55 amSJU - ORD
1 stop10h 11mMultiple Airlines
Deal found 3/31$264
This CheapOair deal was found by Cheapflights users on 3/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2611:45 amORD - STT
2 stops21h 15mSpirit Airlines
Sat 5/311:05 amSTT - ORD
1 stop14h 53mSpirit Airlines
Deal found 3/30$265
This Frontier deal was found by Cheapflights users on 3/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/212:15 pmMDW - SJU
1 stop12h 35mFrontier
Thu 5/810:46 amSJU - MDW
1 stop13h 53mFrontier
Deal found 3/30$296
This Frontier deal was found by Cheapflights users on 3/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/14:15 pmORD - SJU
1 stop9h 36mFrontier
Thu 5/810:46 amSJU - ORD
1 stop13h 25mFrontier
Deal found 3/30$306
This American Airlines deal was found by Cheapflights users on 3/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/95:00 amORD - PUJ
1 stop9h 40mAmerican Airlines
Sun 4/134:40 pmPUJ - ORD
1 stop19h 25mAmerican Airlines
Deal found 3/30$316
This Mytrip deal was found by Cheapflights users on 3/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/86:45 amORD - PUJ
2 stops29h 20mSpirit Airlines
Thu 4/1712:39 pmPUJ - ORD
1 stop20h 25mSpirit Airlines
Deal found 3/30$318
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Tue 4/89:08 pmORD - PUJ
1 stop13h 36mMultiple Airlines
Fri 4/1812:39 pmPUJ - ORD
1 stop27h 19mMultiple Airlines
Deal found 3/30$320
This JetBlue deal was found by Cheapflights users on 3/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/181:35 pmORD - SJU
1 stop11h 10mJetBlue
Tue 9/2311:30 amSJU - ORD
1 stop10h 24mJetBlue
Deal found 3/31$324
This Delta deal was found by Cheapflights users on 3/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/205:30 amORD - PUJ
1 stop6h 45mDelta
Thu 4/243:55 pmPUJ - ORD
1 stop9h 04mDelta
Deal found 3/30$335
This Delta deal was found by Cheapflights users on 3/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/66:04 amMDW - PUJ
1 stop6h 11mDelta
Sat 5/101:05 pmPUJ - MDW
1 stop9h 09mDelta
Deal found 3/30$335
This Booking.com deal was found by Cheapflights users on 3/31. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/185:05 amORD - AUA
1 stop8h 35mSpirit Airlines
Thu 5/223:45 pmAUA - ORD
1 stop9h 20mSpirit Airlines
Deal found 3/31$338

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 April 1, 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

Sun 4/13

8:45 am-11:46 pm

1 stop14h 01m

San Juan Luis Munoz Marin Intl

Wed 4/30

6:35 am-10:58 am

Nonstop5h 23m

$182

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sun 4/27

7:33 pm-10:00 am

1 stop13h 27m

Saint Thomas Island Cyril E King

Wed 4/30

11:05 am-12:20 am

1 stop14h 15m

$261

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 4/15

7:00 pm-8:26 am

1 stop12h 26m

San Juan Luis Munoz Marin Intl

Sun 4/20

5:55 am-3:06 pm

1 stop10h 11m

$264

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 5/2

12:15 pm-1:50 am

1 stop12h 35m

San Juan Luis Munoz Marin Intl

Thu 5/8

10:46 am-11:39 pm

1 stop13h 53m

$296

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 5/1

4:15 pm-2:51 am

1 stop9h 36m

San Juan Luis Munoz Marin Intl

Mon 5/5

10:46 am-11:11 pm

1 stop13h 25m

$306

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 5/11

5:00 am-1:10 pm

1 stop7h 10m

Punta Cana

Thu 5/15

3:16 pm-7:36 pm

Nonstop5h 20m

$317

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 5/5

5:07 pm-11:44 am

1 stop17h 37m

Punta Cana

Thu 5/15

12:42 pm-8:03 pm

1 stop8h 21m

$318

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 4/20

5:30 am-1:15 pm

1 stop6h 45m

Punta Cana

Thu 4/24

3:55 pm-11:59 pm

1 stop9h 04m

$335

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 5/6

6:04 am-2:30 pm

1 stop7h 26m

Punta Cana

Wed 5/14

1:05 pm-9:28 pm

1 stop9h 23m

$335

ChicagoOranjestad

ORD - AUA

ORDAUA

Chicago O'Hare Intl

Sun 5/18

5:05 am-2:40 pm

1 stop8h 35m

Oranjestad Reina Beatrix

Thu 5/22

3:45 pm-12:05 am

1 stop9h 20m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 60 results
1
2
3
...
6

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 December is currently the most expensive (average of $336). 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 April 1, 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 April 1, 2025.

The most flights from USIL to 0CB are scheduled on a Monday (10 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (8 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 April 1, 2025.
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Alaska Airlines
8.0
Very good
9,818 reviews
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Southwest
8.0
Very good
4,276 reviews
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Copa Airlines
7.6
Good
1,400 reviews
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
SWISS
7.5
Good
1,570 reviews
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 Spirit Airlines ($90), American Airlines ($126), and Frontier ($137).

  • 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 December is currently the most expensive (average of $336). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Illinois to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to Miami flights
Newark to Fort Lauderdale flights
Newark to Cancún flights
John F Kennedy Intl to Cancún flights
Newark to Miami flights
LaGuardia to Fort Lauderdale flights
John F Kennedy Intl to Heathrow flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to Los Angeles flights
Los Angeles to John F Kennedy Intl flights
John F Kennedy Intl to Miami flights
Newark to Orlando flights
Newark to Las Vegas flights
Los Angeles to Haneda flights
Dallas/Fort Worth to Cancún flights
Dallas/Fort Worth to Seattle flights
Newark to Heathrow flights
LaGuardia to Orlando flights
John F Kennedy Intl to Charles de Gaulle flights
Dallas/Fort Worth to LaGuardia flights
Newark to Charles de Gaulle flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Leonardo da Vinci/Fiumicino flights
LaGuardia to Dallas/Fort Worth flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Mexico City flights
Newark to Los Angeles flights
John F Kennedy Intl to Haneda flights
San Francisco to John F Kennedy Intl flights
John F Kennedy Intl to Gatwick flights
O'Hare Intl to Cancún flights
Los Angeles to Newark flights
Los Angeles to Honolulu flights
Los Angeles to Narita flights
Dallas/Fort Worth to O'Hare Intl flights
Newark to Seattle flights
Dallas/Fort Worth to Las Vegas flights
Newark to Leonardo da Vinci/Fiumicino flights
Newark to Dallas/Fort Worth flights
LaGuardia to Atlanta flights
Denver to Las Vegas flights
O'Hare Intl to Las Vegas flights
Dulles Intl to Cancún flights
Newark to Narita flights
John F Kennedy Intl to Seattle flights
Newark to Tampa flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
Dallas/Fort Worth to Newark flights
John F Kennedy Intl to San Francisco 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 April 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$352FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$144Average$340FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$193Average$540FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$194Average$683FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$226Average$624FlexibilityNo cancel feeOn-time69%
DeltaCheapest$235Average$651FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$293Average$576FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$335Average$762FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$342Average$680FlexibilityNo cancel feeOn-time63%
AviancaCheapest$397Average$953FlexibilityNo cancel feeOn-time71%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.