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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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
May 30 — Jun 61
Sat 5/30
Sat 6/6
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 April 30, 2026.

This Frontier deal was found by Cheapflights users on 4/29. 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.
Tue 5/2612:33 am
ORD
-
SJU
Nonstop4h 51m
Frontier
Thu 6/117:14 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 4/29$218
This Frontier deal was found by Cheapflights users on 4/28. 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.
Tue 5/193:55 pm
ORD
-
SJU
1 stop9h 13m
Frontier
Wed 5/206:24 pm
SJU
-
ORD
Nonstop5h 22m
Frontier
Deal found 4/28$219
This Priceline deal was found by Cheapflights users on 4/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:30 am
ORD
-
SJU
1 stop14h 58m
Frontier
Sat 5/236:00 am
SJU
-
ORD
1 stop7h 37m
Frontier
Deal found 4/30$221
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sun 5/174:44 pm
ORD
-
SJU
Nonstop4h 37m
Multiple Airlines
Sat 5/233:58 pm
SJU
-
ORD
1 stop8h 15m
Multiple Airlines
Deal found 4/28$222
This Priceline deal was found by Cheapflights users on 4/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:11 pm
ORD
-
SJU
1 stop13h 53m
Multiple Airlines
Thu 5/2811:39 am
SJU
-
ORD
Nonstop5h 10m
Multiple Airlines
Deal found 4/30$223
This Frontier deal was found by Cheapflights users on 4/29. 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 5/155:30 pm
ORD
-
SJU
1 stop7h 38m
Frontier
Thu 5/216:24 pm
SJU
-
ORD
Nonstop5h 22m
Frontier
Deal found 4/29$224
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 5/2312:59 pm
ORD
-
SJU
Nonstop4h 36m
Multiple Airlines
Sun 5/246:24 pm
SJU
-
ORD
Nonstop5h 22m
Multiple Airlines
Deal found 4/28$225
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 8/191:15 pm
ORD
-
SJU
1 stop8h 08m
Delta
Wed 9/25:45 pm
SJU
-
ORD
1 stop7h 12m
Delta
Deal found 4/28$226
This Southwest deal was found by Cheapflights users on 4/28. 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.
Thu 8/207:15 am
MDW
-
SJU
1 stop8h 40m
Southwest
Tue 8/255:15 am
SJU
-
MDW
2 stops7h 50m
Southwest
Deal found 4/28$226
This Expedia deal was found by Cheapflights users on 4/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:52 pm
ORD
-
SJU
1 stop7h 09m
Frontier
Fri 5/227:04 pm
SJU
-
ORD
Nonstop5h 22m
Frontier
Deal found 4/29$227
This Frontier deal was found by Cheapflights users on 4/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
MDW
-
SJU
1 stop7h 07m
Frontier
Fri 5/156:00 am
SJU
-
MDW
1 stop10h 57m
Frontier
Deal found 4/26$227
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 5/114:44 pm
ORD
-
SJU
Nonstop4h 37m
Spirit Airlines
Fri 5/2911:39 am
SJU
-
ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/29$228

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 April 30, 2026.

Round-trip from

$218
(Frontier)

One-way from

$97
(Super.com)

Popular in

December

Cheapest in

January

Average price

$381

Good round-trip deal

$309 or less

Good one-way deal

$138 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 ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 30, 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

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 8/20

7:15 am-4:55 pm

1 stop8h 40m

San Juan Luis Munoz Marin Intl

Mon 8/24

5:30 am-2:55 pm

2 stops10h 25m

$226

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 8/27

2:55 pm-10:15 pm

1 stop6h 20m

San Juan Luis Munoz Marin Intl

Mon 8/31

10:00 am-3:35 pm

1 stop6h 35m

$266

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 8/26

6:00 am-4:35 pm

1 stop9h 35m

San Juan Luis Munoz Marin Intl

Tue 9/1

1:06 pm-9:46 pm

1 stop9h 40m

$296
Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 5/18

8:05 am-12:13 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Thu 5/21

2:30 pm-7:15 pm

Nonstop4h 45m

$318

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 8/14

7:15 am-4:55 pm

1 stop8h 40m

San Juan Luis Munoz Marin Intl

Tue 8/18

6:00 am-1:05 pm

2 stops8h 05m

$331

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 6/2

6:30 am-3:10 pm

1 stop8h 40m

Montego Bay Sangster Intl

Tue 6/9

4:12 pm-11:26 pm

1 stop7h 14m

$332

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 7/24

6:00 am-3:10 pm

1 stop9h 10m

Montego Bay Sangster Intl

Tue 7/28

4:12 pm-11:26 pm

1 stop7h 14m

$332

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 9/21

9:35 pm-11:43 am

1 stop14h 08m

Montego Bay Sangster Intl

Sat 9/26

2:40 pm-10:36 pm

1 stop7h 56m

$332

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 5/7

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Mon 5/11

7:40 am-11:53 am

Nonstop5h 13m

$333

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/12

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Sat 5/16

4:55 pm-11:44 pm

1 stop7h 49m

$345

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 60 resultsSorted by cheapest first
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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

How far ahead should I book a flight from Illinois to Caribbean?

Booking 48 days in advance of your planned departure date is, on average, the best time to get cheap flights from Illinois to Caribbean. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 $390). Flying from Illinois to Caribbean in December is currently the most expensive (average of $585). 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 30, 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 33% 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 April 25, 2026.

Travelers seeking maximum savings on their Illinois to Caribbean flight should consider departing on Wednesday 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 April 30, 2026.

The most flights from USIL to 0CB are scheduled on a Wednesday (9 on average). You will have fewer flight options on Monday, 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 8h 40m. Fly via Southwest, Frontier, or Delta to get the fastest option. The distance from Illinois to Caribbean is about 2057 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 ($79).

  • 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 $390). Flying from Illinois to Caribbean in December is currently the most expensive (average of $585). 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 April 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$100Average$394FlexibilityNo cancel feeOn-time65%
FrontierCheapest$118Average$455FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$119Average$421FlexibilityNo cancel feeOn-time62%
DeltaCheapest$132Average$558FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$175Average$480FlexibilityNo cancel feeOn-time67%
ArajetCheapest$202Average$342FlexibilityNo cancel feeOn-timeN/A
Hahn AirCheapest$213Average$484FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$225Average$617FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$255Average$581FlexibilityNo cancel feeOn-time69%

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