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Caribbean

$97+ 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 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Apr 15 — Apr 221
Wed 4/15
Wed 4/22
1 adult, Economy
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Cheap 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 March 16, 2026.

This eDestinos deal was found by Cheapflights users on 3/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:20 am
ORD
-
SJU
1 stop28h 13m
Frontier
Wed 4/1510:54 am
SJU
-
ORD
1 stop29h 14m
Frontier
Deal found 3/13$201
This Mytrip deal was found by Cheapflights users on 3/12. 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 3/3110:55 am
ORD
-
SJU
1 stop12h 03m
Multiple Airlines
Thu 4/1611:30 am
SJU
-
ORD
1 stop13h 29m
Multiple Airlines
Deal found 3/12$204
This Cheapflightsfares deal was found by Cheapflights users on 3/11. 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.
Tue 3/3110:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Tue 4/71:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/11$208
This Priceline deal was found by Cheapflights users on 3/15. 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.
Mon 4/1310:55 am
ORD
-
SJU
1 stop12h 03m
Multiple Airlines
Thu 4/166:00 am
SJU
-
ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/15$210
This Mytrip deal was found by Cheapflights users on 3/11. 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 3/3110:55 am
ORD
-
SJU
1 stop12h 03m
Multiple Airlines
Tue 4/73:16 am
SJU
-
ORD
1 stop21h 20m
Multiple Airlines
Deal found 3/11$211
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 4/710:55 am
ORD
-
SJU
1 stop12h 03m
Multiple Airlines
Fri 4/173:37 pm
SJU
-
ORD
1 stop8h 29m
Multiple Airlines
Deal found 3/12$212
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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.
Tue 3/3110:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Mon 4/61:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/13$213
This CheapOair deal was found by Cheapflights users on 3/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3110:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Wed 4/81:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/13$214
This Cheapflightsfares deal was found by Cheapflights users on 3/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Wed 4/81:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/14$218
This CheapOair deal was found by Cheapflights users on 3/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:17 am
ORD
-
SJU
1 stop10h 38m
Multiple Airlines
Thu 4/166:30 am
SJU
-
ORD
1 stop9h 38m
Multiple Airlines
Deal found 3/13$220
This Booking.com deal was found by Cheapflights users on 3/15. 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.
Thu 4/92:56 pm
MDW
-
SJU
1 stop8h 56m
Frontier
Thu 4/163:03 pm
SJU
-
MDW
1 stop8h 16m
Frontier
Deal found 3/15$220
This Priceline deal was found by Cheapflights users on 3/11. 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.
Tue 3/314:51 pm
STL
-
SJU
1 stop8h 12m
Frontier
Thu 4/96:33 pm
SJU
-
STL
1 stop14h 18m
Frontier
Deal found 3/11$222

Find flight deals from Illinois to Caribbean

Keep the following information in mind while searching for Illinois to Caribbean flight deals. Data was last updated March 16, 2026.

Round-trip from

$201
(eDestinos)

One-way from

$97
(Super.com)

Popular in

December

Cheapest in

October

Average price

$416

Good round-trip deal

$302 or less

Good one-way deal

$132 or less
From Illinois to Caribbean
Search Deals
One-way flight from Illinois to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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

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 March 16, 2026.
Use the filters below to find and compare flights from Illinois to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 5/5

1:02 pm-8:24 pm

1 stop6h 22m

San Juan Luis Munoz Marin Intl

Sat 5/16

2:48 pm-9:29 pm

1 stop7h 41m

$262

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 4/21

7:45 am-9:24 pm

2 stops12h 39m

San Juan Luis Munoz Marin Intl

Tue 4/28

2:55 pm-10:28 pm

1 stop8h 33m

$285

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Thu 4/9

11:25 am-3:28 pm

2 stops27h 03m

Saint Thomas Island Cyril E King

Wed 4/15

5:10 pm-12:24 am

1 stop8h 14m

$319

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Thu 4/30

11:42 am-8:24 pm

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Tue 5/5

6:15 am-11:56 am

1 stop6h 41m

$325

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 6/9

1:15 pm-10:48 pm

1 stop8h 33m

San Juan Luis Munoz Marin Intl

Tue 6/16

6:15 am-4:44 pm

1 stop11h 29m

$326

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 6/2

5:30 am-4:33 pm

1 stop10h 03m

San Juan Luis Munoz Marin Intl

Tue 6/9

7:00 am-5:41 pm

1 stop11h 41m

$326

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 4/18

8:40 am-12:50 pm

Nonstop4h 10m

Montego Bay Sangster Intl

Sat 4/25

2:40 pm-12:45 am

1 stop10h 05m

$328

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 5/24

8:40 am-3:10 pm

1 stop6h 30m

Montego Bay Sangster Intl

Sun 5/31

4:33 pm-12:45 am

1 stop8h 12m

$342

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 4/21

9:10 am-9:24 pm

2 stops11h 14m

San Juan Luis Munoz Marin Intl

Fri 4/24

1:00 am-10:45 am

2 stops10h 45m

$343

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 7/7

3:30 pm-12:15 am

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Tue 7/14

7:20 pm-7:40 am

1 stop13h 20m

$346

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/15

Showing 1-10 of 60 resultsSorted by cheapest first
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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, April is the cheapest month in which you can book a flight from Illinois to Caribbean (average of $91). Flying from Illinois to Caribbean in December is currently the most expensive (average of $195). 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 March 16, 2026.

One of the essential ways to save on airfare from Illinois to Caribbean is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 37% on airfare.

What is the cheapest day to fly from Illinois to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Illinois to Caribbean. Price data was last updated on March 14, 2026.

Travelers seeking maximum savings on their Illinois to Caribbean flight should consider departing on Tuesday evenings 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

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 March 16, 2026.

The most flights from USIL to 0CB are scheduled on a Saturday (16 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).

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.

  • How long is the flight from Illinois to Caribbean?

    There are many flights that can get you from Illinois to Caribbean in 10h 31m. Fly via Delta, United Airlines, or Spirit Airlines to get the fastest option. The distance from Illinois to Caribbean is about 2024 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 JetBlue ($67), Spirit Airlines ($75), and Frontier ($84).

  • 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, April is the cheapest month in which you can book a flight from Illinois to Caribbean (average of $91). Flying from Illinois to Caribbean in December is currently the most expensive (average of $195). 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

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

Discover the top 9 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 March 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$100Average$394FlexibilityNo cancel feeOn-time65%
FrontierCheapest$112Average$454FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$119Average$443FlexibilityNo cancel feeOn-time62%
DeltaCheapest$132Average$554FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$175Average$522FlexibilityNo cancel feeOn-time67%
Copa AirlinesCheapest$188Average$458FlexibilityNo cancel feeOn-time70%
ArajetCheapest$191Average$325FlexibilityNo cancel feeOn-timeN/A
Hahn AirCheapest$213Average$395FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$225Average$626FlexibilityNo cancel feeOn-time71%

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