$113+ Cheap flights from Chicago (CHI) 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Chicago 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 Chicago to Caribbean
Keep the following information in mind while searching for Chicago to Caribbean flight deals. Data was last updated junio 12, 2025.
Round-trip from | $210 (FlightHub) |
|---|---|
One-way from | $113 (SmartFares) |
Popular in | December |
Cheapest in | September |
Average price | $417 |
Good round-trip deal | $298 or less |
Good one-way deal | $150 or less |
Find flight deals from Chicago to Caribbean
Cheapest flights from Chicago to CaribbeanExplore the most affordable flight options available from Chicago to Caribbean. 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 Chicago to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on junio 12, 2025.
This FlightHub 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 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 Cheapflightsfares 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 Cheapflightsfares 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 6/11. 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 Priceline 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 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 Cheapflightsfares 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 Vliegwinkel 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 Vliegwinkel 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.
This Kissandfly.com 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 Kissandfly.com 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 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 Cheapflightsfares 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 6/12. 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 American 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 Chicago 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 junio 12, 2025.
Use the filters below to find and compare flights from Chicago to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
lun. 8/18
7:45 am-4:43 pm
1 stop7h 58m
San Juan Luis Munoz Marin Intl
jue. 8/21
3:21 pm-11:54 pm
1 stop9h 33m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
vie. 8/29
2:05 pm-11:54 pm
1 stop8h 49m
San Juan Luis Munoz Marin Intl
vie. 9/5
4:42 pm-11:56 am
1 stop20h 14m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
mar. 7/8
10:43 am-12:05 am
1 stop12h 22m
San Juan Luis Munoz Marin Intl
mar. 7/15
4:43 pm-7:04 am
1 stop15h 21m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
sáb. 7/12
12:20 pm-12:27 am
1 stop11h 07m
San Juan Luis Munoz Marin Intl
mar. 7/22
4:43 pm-7:04 am
1 stop15h 21m
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
mar. 7/8
7:49 pm-12:30 pm
1 stop15h 41m
Saint Thomas Island Cyril E King
mar. 7/15
1:25 pm-11:11 pm
1 stop10h 46m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
mar. 7/1
8:35 am-2:10 pm
Nonstop4h 35m
Punta Cana
vie. 7/4
3:31 pm-7:36 pm
Nonstop5h 05m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
lun. 7/14
8:45 pm-11:01 am
1 stop13h 16m
Punta Cana
mar. 7/22
4:10 pm-9:35 am
2 stops18h 25m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
mar. 7/1
6:03 pm-11:54 pm
Nonstop4h 51m
San Juan Luis Munoz Marin Intl
lun. 7/7
1:10 am-10:53 am
1 stop10h 43m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
lun. 7/14
8:45 pm-2:00 pm
1 stop16h 15m
Punta Cana
mié. 7/16
1:50 pm-5:55 pm
Nonstop5h 05m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
mié. 8/20
6:00 am-2:57 pm
1 stop7h 57m
San Juan Luis Munoz Marin Intl
dom. 8/24
2:59 pm-9:58 pm
1 stop7h 59m
Best time to book a flight from Chicago to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Chicago with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Caribbean
What is the cheapest month to book a flight from Chicago to Caribbean?
Currently, September is the cheapest month in which you can book a flight from Chicago to Caribbean (average of $254). Flying from Chicago to Caribbean in June is currently the most expensive (average of $339). 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 CHI to CB?
Find hourly flight availability from Chicago 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 junio 12, 2025.
When flying from Chicago to Caribbean, 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 Chicago to Caribbean
Explore weekly flight availability from Chicago 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 junio 12, 2025.
The most flights from CHI 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 junio 12, 2025.
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
Kim,May 2025
PIH - SLC
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
Kim,May 2025
PIH - SLC
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
Kim,May 2025
PIH - SLC
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
Kim,May 2025
PIH - SLC
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
Kim,May 2025
PIH - SLC
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
Kim,May 2025
PIH - SLC
Related info for your journey
Find useful and relevant information for your journey from Chicago to Caribbean. 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 Chicago to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Top 10 airlines flying from Chicago to Caribbean
Discover the top 10 airlines that operate flights from Chicago 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 junio 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$106 | Average$374 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$140 | Average$361 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$193 | Average$538 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$202 | Average$483 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$216 | Average$631 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$226 | Average$619 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$240 | Average$330 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$335 | Average$751 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$338 | Average$645 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$354 | Average$654 | FlexibilityNo cancel fee | On-time63% |