$102+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
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 17, 2025.
Round-trip from | $216 (eDestinos) |
|---|---|
One-way from | $102 (Cheapflightsfares) |
Popular in | December |
Cheapest in | August |
Average price | $351 |
Good round-trip deal | $328 or less |
Good one-way deal | $166 or less |
Find flight deals from Illinois to Caribbean
Cheapest flights from Illinois to CaribbeanExplore 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 17, 2025.
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 17, 2025.
This United Airlines deal was found by Cheapflights users on 4/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This eDestinos deal was found by Cheapflights users on 4/17. 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.
This Delta deal was found by Cheapflights users on 4/17. 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.
This Flightnetwork deal was found by Cheapflights users on 4/16. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This American Airlines deal was found by Cheapflights users on 4/16. 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.
This CheapOair deal was found by Cheapflights users on 4/17. 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.
This Mytrip deal was found by Cheapflights users on 4/17. 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.
This Frontier deal was found by Cheapflights users on 4/17. 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.
This Frontier deal was found by Cheapflights users on 4/17. 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.
This Frontier deal was found by Cheapflights users on 4/16. 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.
This Frontier deal was found by Cheapflights users on 4/16. 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.
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
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 17, 2025.
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
St. LouisSan Juan
STL - SJU
STLSJU
Lambert-St Louis
Wed 5/7
6:00 am-3:40 pm
1 stop8h 40m
San Juan Luis Munoz Marin Intl
Fri 5/9
1:05 am-2:50 pm
2 stops14h 45m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 5/11
11:30 am-5:16 pm
Nonstop4h 46m
San Juan Luis Munoz Marin Intl
Thu 5/15
6:09 am-10:25 am
Nonstop5h 16m
St. LouisSan Juan
STL - SJU
STLSJU
Lambert-St Louis
Thu 7/17
9:00 am-7:44 pm
1 stop9h 44m
San Juan Luis Munoz Marin Intl
Wed 7/23
2:15 pm-8:30 pm
1 stop7h 15m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 5/10
4:35 pm-10:45 am
1 stop17h 10m
San Juan Luis Munoz Marin Intl
Sat 5/17
9:58 pm-8:43 am
1 stop11h 45m
St. LouisSan Juan
STL - SJU
STLSJU
Lambert-St Louis
Wed 5/7
7:10 am-8:33 pm
1 stop12h 23m
San Juan Luis Munoz Marin Intl
Thu 5/8
5:25 am-8:58 pm
1 stop16h 33m
St. LouisSan Juan
STL - SJU
STLSJU
Lambert-St Louis
Fri 5/2
5:55 pm-2:51 am
1 stop7h 56m
San Juan Luis Munoz Marin Intl
Tue 5/6
9:25 am-5:15 pm
1 stop8h 50m
St. LouisSan Juan
STL - SJU
STLSJU
Lambert-St Louis
Sun 5/18
10:10 am-7:07 pm
1 stop7h 57m
San Juan Luis Munoz Marin Intl
Sat 5/24
8:12 pm-9:15 am
1 stop14h 03m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 5/4
4:15 pm-12:05 am
1 stop6h 50m
San Juan Luis Munoz Marin Intl
Fri 5/9
2:34 pm-11:32 pm
1 stop9h 58m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 5/2
1:19 pm-10:01 pm
1 stop7h 42m
San Juan Luis Munoz Marin Intl
Sun 5/4
9:58 pm-5:28 pm
1 stop20h 30m
St. LouisSan Juan
STL - SJU
STLSJU
Lambert-St Louis
Thu 5/8
5:45 pm-2:51 am
1 stop8h 06m
San Juan Luis Munoz Marin Intl
Sun 5/11
4:39 pm-12:06 am
1 stop8h 27m
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.
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 17, 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 17, 2025.
The most flights from USIL to 0CB are scheduled on a Monday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 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 17, 2025.
Crew
Boarding
Overall
Entertainment
Food
Comfort
Reviews
Anonymous,Apr 2025
LAS - STS
Crew
Boarding
Overall
Entertainment
Food
Comfort
Reviews
Anonymous,Apr 2025
LAS - STS
Crew
Boarding
Overall
Entertainment
Food
Comfort
Reviews
Anonymous,Apr 2025
LAS - STS
Crew
Boarding
Overall
Entertainment
Food
Comfort
Reviews
Anonymous,Apr 2025
LAS - STS
Crew
Boarding
Overall
Entertainment
Food
Comfort
Reviews
Anonymous,Apr 2025
LAS - STS
Crew
Boarding
Overall
Entertainment
Food
Comfort
Reviews
Anonymous,Apr 2025
LAS - STS
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.
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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.
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 17, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$124 | Average$348 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$144 | Average$359 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$194 | Average$676 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$222 | Average$637 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$226 | Average$671 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$226 | Average$537 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$293 | Average$503 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$335 | Average$768 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$342 | Average$672 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$397 | Average$953 | FlexibilityNo cancel fee | On-time71% |