$112+ Cheap flights from O'Hare Intl (ORD) to Caribbean Islands
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 6/24. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from O'Hare Intl to Caribbean Islands 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 O'Hare Intl to Caribbean Islands
Keep the following information in mind while searching for O'Hare Intl to Caribbean Islands flight deals. Data was last updated 5月 11, 2025.
Round-trip from | $209 (eDestinos) |
|---|---|
One-way from | $112 (Mytrip) |
Popular in | December |
Cheapest in | August |
Average price | $343 |
Find flight deals from O'Hare Intl to Caribbean Islands
Cheapest flights from O'Hare Intl to Caribbean IslandsExplore the most affordable flight options available from O'Hare Intl to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 5月 11, 2025.
Explore the most affordable flight options available from O'Hare Intl to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 5月 11, 2025.
This eDestinos deal was found by Cheapflights users on 5/11. 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 eDestinos 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 5/11. 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 5/10. 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 Booking.com deal was found by Cheapflights users on 5/10. 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 Booking.com 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 5/9. 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 American Airlines deal was found by Cheapflights users on 5/10. 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 CheapOair deal was found by Cheapflights users on 5/10. 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 CheapOair 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 5/11. 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 Frontier 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 5/11. 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 Delta deal was found by Cheapflights users on 5/11. 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 Delta 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 5/11. 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 United Airlines 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 5/10. 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.
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl to Caribbean Islands 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 5月 11, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Caribbean Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
火 6/3
11:30 am-5:16 pm
Nonstop4h 46m
San Juan Luis Munoz Marin Intl
金 6/6
8:12 pm-8:50 am
1 stop13h 38m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
土 8/16
10:00 am-3:51 pm
Nonstop4h 51m
San Juan Luis Munoz Marin Intl
月 9/8
3:21 pm-12:10 am
1 stop9h 49m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
水 5/28
5:05 am-2:17 pm
1 stop8h 12m
Punta Cana
水 6/4
3:22 pm-11:04 pm
1 stop8h 42m
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
木 6/5
7:35 pm-9:57 am
1 stop13h 22m
Saint Thomas Island Cyril E King
土 6/7
2:41 pm-11:29 pm
1 stop9h 48m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
水 7/2
5:05 am-2:10 pm
1 stop8h 05m
Punta Cana
水 7/9
5:08 pm-9:16 pm
Nonstop5h 08m
ChicagoChristiansted
ORD - STX
ORDSTX
Chicago O'Hare Intl
火 6/17
5:05 am-3:49 pm
1 stop9h 44m
Christiansted Henry Rohlsen
火 6/24
4:48 pm-8:50 am
1 stop17h 02m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
木 6/12
8:50 pm-10:50 am
1 stop13h 00m
Punta Cana
木 6/19
1:35 pm-7:25 am
2 stops18h 50m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
金 5/23
5:14 pm-2:32 am
1 stop8h 18m
San Juan Luis Munoz Marin Intl
土 5/31
12:06 pm-12:04 am
1 stop12h 58m
ChicagoOranjestad
ORD - AUA
ORDAUA
Chicago O'Hare Intl
土 6/7
5:05 am-2:40 pm
1 stop8h 35m
Oranjestad Reina Beatrix
土 6/14
3:45 pm-11:45 pm
1 stop9h 00m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
月 8/11
7:10 am-2:30 pm
1 stop6h 20m
Punta Cana
金 8/15
1:10 pm-9:21 pm
1 stop9h 11m
Best time to book a flight from O'Hare Intl to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from O'Hare Intl with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Chicago O'Hare Intl Airport to Caribbean Islands
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Caribbean Islands?
Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean Islands (average of $254). Flying from Chicago O'Hare Intl Airport to Caribbean Islands 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 ORD to EPX?
Find hourly flight availability from O'Hare Intl to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 5月 11, 2025.
When flying from Chicago O'Hare Intl Airport to Caribbean Islands, 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 O'Hare Intl Airport to Caribbean Islands
Explore weekly flight availability from O'Hare Intl to Caribbean Islands. 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 5月 11, 2025.
The most flights from ORD to zzEPX are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (8 on average).
Rainfall in Caribbean Islands by month
Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.
Temperature in Caribbean Islands by month
Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Caribbean Islands, 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 Islands
Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated 5月 11, 2025.
Read reviews from past customers who have flown Delta, Alaska Airlines and Southwest from Chicago to Caribbean Islands. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
Comfort
Food
Boarding
Overall
Entertainment
Reviews
Kim,May 2025
PIH - SLC
Crew
Comfort
Food
Boarding
Overall
Entertainment
Reviews
Kim,May 2025
PIH - SLC
Crew
Comfort
Food
Boarding
Overall
Entertainment
Reviews
Kim,May 2025
PIH - SLC
Crew
Comfort
Food
Boarding
Overall
Entertainment
Reviews
Kim,May 2025
PIH - SLC
Crew
Comfort
Food
Boarding
Overall
Entertainment
Reviews
Kim,May 2025
PIH - SLC
Crew
Comfort
Food
Boarding
Overall
Entertainment
Reviews
Kim,May 2025
PIH - SLC
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Caribbean Islands. 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
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for O'Hare Intl to Caribbean Islands
See prices for flight routes from nearby airports that may be better suited for you.
Top 10 airlines flying from O'Hare Intl to Caribbean Islands
Discover the top 10 airlines that operate flights from O'Hare Intl to Caribbean Islands. 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 5月 11, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$124 | Average$351 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$141 | Average$375 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$193 | Average$542 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$216 | Average$610 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$226 | Average$643 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$293 | Average$487 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$335 | Average$768 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$336 | Average$648 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$385 | Average$484 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$397 | Average$953 | FlexibilityNo cancel fee | On-time71% |