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Caribbean

$87+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

This Frontier deal was found by Cheapflights users on 1/25. 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.
Sat 2/213:49 pm
STL
-
SJU
1 stop9h 04m
Frontier
Tue 3/311:07 am
SJU
-
STL
1 stop13h 20m
Frontier
Deal found 1/25$178
This Priceline deal was found by Cheapflights users on 1/26. 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 2/233:49 pm
STL
-
SJU
1 stop9h 04m
Frontier
Sat 2/285:25 pm
SJU
-
STL
1 stop8h 34m
Frontier
Deal found 1/26$182
This CheapOair deal was found by Cheapflights users on 1/25. 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.
Mon 2/212:17 pm
ORD
-
SJU
Nonstop4h 32m
Multiple Airlines
Mon 2/93:53 am
SJU
-
ORD
1 stop13h 59m
Multiple Airlines
Deal found 1/25$185
This Travelocity deal was found by Cheapflights users on 1/27. 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.
Tue 4/218:31 am
ORD
-
SJU
1 stop8h 59m
Multiple Airlines
Mon 4/276:00 am
SJU
-
ORD
1 stop17h 57m
Multiple Airlines
Deal found 1/27$186
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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.
Mon 2/912:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Sat 2/1412:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/27$187
This Trip.com deal was found by Cheapflights users on 1/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:17 pm
ORD
-
SJU
Nonstop4h 32m
Multiple Airlines
Tue 2/241:44 pm
SJU
-
ORD
1 stop11h 15m
Multiple Airlines
Deal found 1/24$188
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/178:30 am
ORD
-
SJU
1 stop16h 18m
Frontier
Tue 2/245:25 pm
SJU
-
ORD
1 stop24h 27m
Frontier
Deal found 1/25$189
This Kiwi.com deal was found by Cheapflights users on 1/26. 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
Spirit Airlines
Mon 4/131:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/26$190
This JetBlue deal was found by Cheapflights users on 1/27. 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.
Wed 2/1810:00 am
ORD
-
SJU
1 stop10h 53m
JetBlue
Thu 2/261:44 pm
SJU
-
ORD
1 stop11h 15m
JetBlue
Deal found 1/27$191
This JetBlue deal was found by Cheapflights users on 1/26. 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.
Wed 4/88:15 am
ORD
-
SJU
1 stop7h 40m
JetBlue
Fri 4/1711:59 pm
SJU
-
ORD
1 stop8h 42m
JetBlue
Deal found 1/26$192
This Priceline deal was found by Cheapflights users on 1/26. 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.
Sat 4/1110:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Mon 4/131:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/26$193
This CheapOair deal was found by Cheapflights users on 1/25. 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.
Thu 4/169:14 am
MDW
-
SJU
1 stop15h 47m
Frontier
Sat 4/258:00 am
SJU
-
MDW
1 stop9h 13m
Frontier
Deal found 1/25$193

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 January 27, 2026.

Round-trip from

$178
(Frontier)

One-way from

$87
(Priceline)

Popular in

December

Cheapest in

April

Average price

$358

Good round-trip deal

$303 or less

Good one-way deal

$128 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 ($47 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 January 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 January 27, 2026.
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

Wed 2/18

10:00 am-10:53 pm

1 stop10h 53m

San Juan Luis Munoz Marin Intl

Tue 2/24

5:10 am-11:59 am

1 stop8h 49m

$191

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 3/13

5:00 pm-1:42 am

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Tue 3/24

3:26 am-11:25 am

1 stop8h 59m

$197

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 3/13

5:00 pm-1:42 am

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Mon 3/23

3:26 am-11:25 am

1 stop8h 59m

$197

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 3/10

12:39 pm-11:29 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Fri 3/13

3:26 am-11:25 am

1 stop8h 59m

$197

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 4/14

4:55 pm-2:01 am

1 stop8h 06m

San Juan Luis Munoz Marin Intl

Wed 4/15

11:07 am-11:19 pm

1 stop13h 12m

$203

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 4/15

8:31 am-6:30 pm

1 stop8h 59m

San Juan Luis Munoz Marin Intl

Tue 4/21

11:25 pm-8:51 am

1 stop10h 26m

$203

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 3/12

12:20 pm-8:26 pm

1 stop7h 06m

San Juan Luis Munoz Marin Intl

Mon 3/23

3:26 am-11:25 am

1 stop8h 59m

$212

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 3/7

12:59 pm-10:24 pm

1 stop7h 25m

San Juan Luis Munoz Marin Intl

Tue 3/10

4:15 am-11:48 am

1 stop8h 33m

$212

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 3/24

12:20 pm-8:26 pm

1 stop7h 06m

San Juan Luis Munoz Marin Intl

Thu 3/26

3:26 am-11:25 am

1 stop8h 59m

$212

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 4/9

10:00 am-10:01 pm

1 stop11h 01m

San Juan Luis Munoz Marin Intl

Fri 4/17

11:59 pm-7:41 am

1 stop8h 42m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

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 $126). 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 January 27, 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 40% 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 January 24, 2026.

Travelers seeking maximum savings on their Illinois to Caribbean flight should consider departing on Tuesday mornings 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 January 27, 2026.

The most flights from USIL to 0CB are scheduled on a Monday (11 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (9 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 8h 06m. Fly via JetBlue, Frontier, or American 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), Frontier ($74), and Spirit Airlines ($87).

  • 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 $126). 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

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.
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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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$450FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$119Average$445FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$130Average$343FlexibilityNo cancel feeOn-time65%
DeltaCheapest$136Average$569FlexibilityNo cancel feeOn-timeN/A
ArajetCheapest$185Average$320FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$193Average$576FlexibilityNo cancel feeOn-time67%
Hahn AirCheapest$213Average$343FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$616FlexibilityNo cancel feeOn-time69%

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