$89+ Cheap flights from Caribbean to Illinois
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 7/13. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Caribbean to Illinois 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 Caribbean to Illinois
Keep the following information in mind while searching for Caribbean to Illinois flight deals. Data was last updated junio 12, 2025.
Round-trip from | $191 (Booking.com) |
|---|---|
One-way from | $89 (FlightHub) |
Popular in | March |
Cheapest in | January |
Average price | $298 |
Good round-trip deal | $255 or less |
Good one-way deal | $189 or less |
Find flight deals from Caribbean to Illinois
Cheapest flights from Caribbean to IllinoisExplore the most affordable flight options available from Caribbean to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on junio 12, 2025.
Explore the most affordable flight options available from Caribbean to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on junio 12, 2025.
This Booking.com deal was found by Cheapflights users on 6/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Priceline deal was found by Cheapflights users on 6/12. 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.
This Priceline deal was found by Cheapflights users on 6/10. 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.
This Priceline deal was found by Cheapflights users on 6/12. 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.
This Priceline deal was found by Cheapflights users on 6/12. 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.
This Southwest deal was found by Cheapflights users on 6/10. 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 Delta deal was found by Cheapflights users on 6/12. 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 FlightHub deal was found by Cheapflights users on 6/11. 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 Priceline deal was found by Cheapflights users on 6/10. 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.
This American Airlines deal was found by Cheapflights users on 6/10. 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 JetBlue deal was found by Cheapflights users on 6/10. 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 United Airlines deal was found by Cheapflights users on 6/10. 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.
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean to Illinois 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 junio 12, 2025.
Use the filters below to find and compare flights from Caribbean to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
mar. 7/15
3:50 pm-11:13 pm
1 stop8h 23m
Chicago O'Hare Intl
mar. 7/22
5:05 am-3:30 pm
1 stop9h 25m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
vie. 9/5
3:40 am-2:53 pm
1 stop12h 13m
Chicago O'Hare Intl
jue. 9/11
6:20 am-11:58 pm
1 stop16h 38m
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
jue. 9/25
4:42 pm-1:17 pm
1 stop21h 35m
Lambert-St Louis
lun. 9/29
2:12 pm-2:34 am
1 stop11h 22m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
jue. 9/11
1:11 am-7:20 am
1 stop7h 09m
Chicago Midway
dom. 9/21
8:15 am-11:58 pm
1 stop14h 43m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
jue. 6/26
8:24 pm-8:50 am
1 stop13h 26m
Chicago O'Hare Intl
jue. 8/28
6:35 am-11:54 pm
1 stop16h 19m
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
jue. 9/25
11:10 am-10:35 pm
2 stops12h 25m
Lambert-St Louis
lun. 9/29
2:00 pm-11:50 pm
1 stop8h 50m
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
jue. 7/31
6:15 am-4:18 pm
1 stop11h 03m
Lambert-St Louis
mié. 8/13
9:17 am-4:36 pm
1 stop6h 19m
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
sáb. 7/19
1:37 am-9:52 am
1 stop9h 15m
Lambert-St Louis
dom. 7/27
10:47 am-11:32 am
1 stop23h 45m
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
jue. 6/26
9:30 pm-11:53 pm
1 stop27h 23m
Lambert-St Louis
lun. 6/30
11:28 am-7:19 pm
1 stop6h 51m
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
mié. 7/9
3:31 pm-7:36 pm
Nonstop5h 05m
Chicago O'Hare Intl
mié. 8/13
8:34 pm-11:05 am
1 stop13h 31m
Best time to book a flight from Caribbean to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Caribbean with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Caribbean to Illinois
What is the cheapest month to book a flight from Caribbean to Illinois?
Currently, August is the cheapest month in which you can book a flight from Caribbean to Illinois (average of $245). Flying from Caribbean to Illinois in March is currently the most expensive (average of $321). 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 CB to IL?
Find hourly flight availability from Caribbean to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated junio 12, 2025.
When flying from Caribbean to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Caribbean to Illinois
Explore weekly flight availability from Caribbean to Illinois. 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 junio 12, 2025.
The most flights from 0CB to USIL are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).
Rainfall in Illinois by month
Plan your trip to Illinois by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.
Temperature in Illinois by month
Plan your trip to Illinois by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated junio 12, 2025.
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
John,May 2025
PVD - BNA
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
John,May 2025
PVD - BNA
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
John,May 2025
PVD - BNA
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
John,May 2025
PVD - BNA
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
John,May 2025
PVD - BNA
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
John,May 2025
PVD - BNA
Related info for your journey
Find useful and relevant information for your journey from Caribbean to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Caribbean to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Caribbean to Illinois
Discover the top 6 airlines that operate flights from Caribbean to Illinois. 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 junio 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$326 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$137 | Average$293 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$172 | Average$438 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$217 | Average$528 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$257 | Average$495 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$329 | Average$558 | FlexibilityNo cancel fee | On-time71% |