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$101+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 October 28, 2025.

Round-trip from

$209
(Frontier)

One-way from

$101
(Expedia)

Popular in

December

Cheapest in

April

Average price

$360

Good round-trip deal

$350 or less

Good one-way deal

$191 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. 7% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1511:35 amORD - SJU
1 stop13h 58mMultiple Airlines
Fri 11/217:10 amSJU - ORD
1 stop12h 49mMultiple Airlines
Deal found 10/27$212
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Thu 11/2712:55 pmORD - SJU
1 stop11h 59mMultiple Airlines
Thu 12/410:42 amSJU - ORD
1 stop9h 54mMultiple Airlines
Deal found 10/28$213
This Frontier deal was found by Cheapflights users on 10/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:15 pmORD - SJU
1 stop8h 14mFrontier
Thu 1/157:00 amSJU - ORD
1 stop14h 00mFrontier
Deal found 10/27$214
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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.
Wed 12/315:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Wed 1/78:01 pmSJU - ORD
Nonstop5h 20mSpirit Airlines
Deal found 10/27$217
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Sun 11/1612:17 pmORD - SJU
1 stop11h 15mMultiple Airlines
Sun 11/234:12 pmSJU - ORD
Nonstop5h 11mMultiple Airlines
Deal found 10/25$218
This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/278:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Thu 12/49:00 amSJU - ORD
Nonstop5h 23mSpirit Airlines
Deal found 10/28$219
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:40 amORD - SJU
2 stops30h 02mMultiple Airlines
Fri 11/215:19 pmSJU - ORD
1 stop17h 58mMultiple Airlines
Deal found 10/27$220
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/186:00 amSTL - SJU
2 stops12h 48mAmerican Airlines
Wed 11/196:25 amSJU - STL
1 stop16h 35mAmerican Airlines
Deal found 10/28$220
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Wed 11/266:15 pmORD - SJU
1 stop24h 57mMultiple Airlines
Thu 12/410:42 amSJU - ORD
1 stop9h 54mMultiple Airlines
Deal found 10/28$221
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Thu 11/274:00 pmMDW - SJU
2 stops39h 27mFrontier
Thu 12/410:42 amSJU - MDW
1 stop13h 11mFrontier
Deal found 10/28$221
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/117:34 pmORD - SJU
1 stop20h 20mMultiple Airlines
Thu 11/209:30 pmSJU - ORD
1 stop15h 05mMultiple Airlines
Deal found 10/27$222
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Sun 11/1612:17 pmORD - SJU
1 stop11h 15mMultiple Airlines
Sat 11/229:30 pmSJU - ORD
2 stops39h 41mMultiple Airlines
Deal found 10/26$223

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 October 28, 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

Mon 1/12

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Thu 1/15

8:35 am-11:57 am

Nonstop5h 22m

$218

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 11/18

10:00 am-10:22 pm

2 stops10h 22m

San Juan Luis Munoz Marin Intl

Thu 11/20

8:10 am-3:46 pm

1 stop9h 36m

$225

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Mon 2/16

9:30 am-4:18 pm

Nonstop4h 48m

Saint Thomas Island Cyril E King

Thu 2/19

3:05 pm-6:45 pm

Nonstop5h 40m

$242

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 11/18

10:00 am-10:22 pm

2 stops10h 22m

San Juan Luis Munoz Marin Intl

Tue 11/18

2:05 am-10:40 am

1 stop10h 35m

$243

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/31

1:00 pm-12:36 am

1 stop9h 36m

San Juan Luis Munoz Marin Intl

Mon 2/2

2:05 am-9:40 am

1 stop9h 35m

$262

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/28

6:20 pm-6:11 am

1 stop9h 51m

San Juan Luis Munoz Marin Intl

Tue 3/3

8:10 am-2:20 pm

1 stop8h 10m

$285

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 2/17

2:30 pm-12:36 am

1 stop8h 06m

San Juan Luis Munoz Marin Intl

Tue 2/24

4:52 pm-8:20 pm

Nonstop5h 28m

$302

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 12/5

8:45 am-5:25 pm

1 stop6h 40m

Punta Cana

Fri 12/12

12:56 pm-11:44 pm

1 stop12h 48m

$303

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 12/5

8:45 am-5:25 pm

1 stop6h 40m

Punta Cana

Wed 12/10

5:20 pm-11:43 pm

1 stop8h 23m

$303

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 12/24

6:45 am-4:23 pm

1 stop7h 38m

San Juan Luis Munoz Marin Intl

Fri 1/2

2:21 pm-10:04 pm

1 stop9h 43m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

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, February is the cheapest month in which you can book a flight from Illinois to Caribbean (average of $127). Flying from Illinois to Caribbean in December is currently the most expensive (average of $188). 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 October 28, 2025.

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 32% 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 December 16, 2024.

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 mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 4h 40m. Fly via United Airlines, Southwest, or Frontier to get the fastest option. The distance from Illinois to Caribbean is about 2073 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 Spirit Airlines ($101), United Airlines ($109), and Delta ($113).

  • 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, February is the cheapest month in which you can book a flight from Illinois to Caribbean (average of $127). Flying from Illinois to Caribbean in December is currently the most expensive (average of $188). 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$450FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$140Average$393FlexibilityNo cancel feeOn-time65%
DeltaCheapest$186Average$626FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$188Average$431FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$225Average$649FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$226Average$641FlexibilityNo cancel feeOn-time69%
ArajetCheapest$233Average$331FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$261Average$470FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$380Average$662FlexibilityNo cancel feeOn-time63%

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