$82+ 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 2/7. 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
Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 21, 2025.
Round-trip from | $160 (Booking.com) |
|---|---|
One-way from | $82 (Cheapflightsfares) |
Good round-trip deal | $295 or less |
Good one-way deal | $185 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 enero 21, 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 enero 21, 2025.
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
This FlightHub deal was found by Cheapflights users on 1/21. 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 FlightHub 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 1/20. 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.
This Frontier deal was found by Cheapflights users on 1/21. 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 Southwest deal was found by Cheapflights users on 1/20. 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.
This United Airlines deal was found by Cheapflights users on 1/21. 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 Kiwi.com deal was found by Cheapflights users on 1/20. 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.
This JetBlue deal was found by Cheapflights users on 1/20. 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.
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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.
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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.
This CheapOair deal was found by Cheapflights users on 1/21. 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 1/21. 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.
Find flights from Illinois to Caribbean within your budget
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 enero 21, 2025.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
mar. 2/25
12:21 pm-6:52 pm
Nonstop4h 31m
San Juan Luis Munoz Marin Intl
jue. 3/6
7:00 am-10:36 am
Nonstop5h 36m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
mar. 4/1
2:36 pm-11:54 pm
1 stop8h 18m
San Juan Luis Munoz Marin Intl
lun. 4/7
5:01 am-7:46 pm
1 stop15h 45m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
mar. 3/4
3:14 pm-9:49 am
1 stop16h 35m
San Juan Luis Munoz Marin Intl
mié. 3/12
5:45 pm-12:07 am
1 stop7h 22m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
vie. 2/21
7:18 pm-9:49 am
1 stop12h 31m
San Juan Luis Munoz Marin Intl
mar. 2/25
9:30 pm-9:27 am
1 stop13h 57m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
dom. 2/2
1:20 pm-12:50 am
2 stops9h 30m
San Juan Luis Munoz Marin Intl
vie. 2/7
1:45 pm-10:00 pm
1 stop10h 15m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
dom. 2/2
10:35 am-9:28 pm
1 stop8h 53m
San Juan Luis Munoz Marin Intl
lun. 12/8
2:05 am-9:37 am
1 stop9h 32m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
vie. 2/7
8:12 pm-11:10 am
1 stop12h 58m
Punta Cana
jue. 2/20
2:29 pm-11:20 pm
1 stop10h 51m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
mié. 2/19
12:45 pm-1:13 am
1 stop10h 28m
San Juan Luis Munoz Marin Intl
jue. 2/27
5:10 am-10:59 am
1 stop7h 49m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
lun. 2/24
7:10 am-3:43 pm
1 stop6h 33m
Punta Cana
vie. 2/28
4:48 pm-11:58 pm
1 stop9h 10m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
mar. 4/1
2:36 pm-10:18 am
1 stop18h 42m
Punta Cana
lun. 4/7
2:49 pm-11:50 pm
1 stop10h 01m
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.
Travel insights for flights from Illinois to Caribbean
Get recent, data-driven insights about flights from Illinois to Caribbean including ideal travel times, pricing trends, and more.
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 March is currently the most expensive (average of $378). 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 enero 21, 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 enero 21, 2025.
The most flights from USIL to 0CB are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 enero 21, 2025.
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
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 enero 21, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$124 | Average$367 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$155 | Average$361 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$194 | Average$689 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$226 | Average$518 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$258 | Average$640 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$274 | Average$499 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$317 | Average$675 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$324 | Average$691 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$335 | Average$839 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$1,422 | Average$1,422 | FlexibilityNo cancel fee | On-time71% |