$90+ Cheap flights from O'Hare Intl (ORD) 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 2/9. 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 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
Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) 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 January 4, 2025.
Round-trip from | $157 (FlightHub) |
|---|---|
One-way from | $90 (Priceline) |
Find flight deals from O'Hare Intl to Caribbean
Cheapest flights from O'Hare Intl to CaribbeanExplore the most affordable flight options available from O'Hare Intl to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 4, 2025.
Explore the most affordable flight options available from O'Hare Intl to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 4, 2025.
This Cheapflightsfares deal was found by Cheapflights users on 1/3. 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 FlightHub deal was found by Cheapflights users on 1/3. 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 1/3. 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 United Airlines deal was found by Cheapflights users on 1/3. 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 1/3. 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 Kiwi.com deal was found by Cheapflights users on 1/3. 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 eDestinos deal was found by Cheapflights users on 1/3. 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 JetBlue Airways deal was found by Cheapflights users on 1/3. 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 Airways 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 1/2. 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 American Airlines deal was found by Cheapflights users on 1/3. 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 Delta deal was found by Cheapflights users on 1/3. 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 Mytrip deal was found by Cheapflights users on 1/3. 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 O'Hare Intl to Caribbean within your budget
Customize your flight search to find flights from O'Hare Intl 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 January 4, 2025.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 2/15
8:44 pm-12:48 am
1 stop26h 04m
San Juan Luis Munoz Marin Intl
Fri 2/21
3:54 am-7:39 pm
1 stop17h 45m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 1/19
6:06 pm-11:18 am
1 stop15h 12m
San Juan Luis Munoz Marin Intl
Fri 1/31
9:26 pm-12:51 am
Nonstop5h 25m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 2/21
7:18 pm-9:35 am
1 stop12h 17m
San Juan Luis Munoz Marin Intl
Wed 2/26
8:31 pm-11:55 pm
Nonstop5h 24m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 3/1
6:35 pm-6:12 am
1 stop9h 37m
San Juan Luis Munoz Marin Intl
Thu 3/6
2:05 am-9:07 am
1 stop9h 02m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Thu 1/30
6:10 am-1:00 pm
Nonstop4h 50m
Punta Cana
Thu 2/6
6:54 pm-10:11 pm
Nonstop5h 17m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 2/3
5:11 am-3:45 pm
1 stop8h 34m
Punta Cana
Fri 2/7
6:10 pm-9:27 pm
Nonstop5h 17m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sun 2/2
5:11 am-3:45 pm
1 stop8h 34m
Punta Cana
Thu 2/6
4:50 pm-11:32 pm
1 stop8h 42m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 3/7
11:44 am-9:50 pm
1 stop8h 06m
San Juan Luis Munoz Marin Intl
Sun 3/9
5:01 am-12:15 pm
1 stop8h 14m
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Mon 1/27
5:28 pm-11:20 am
2 stops15h 52m
Simpson Bay Princess Juliana
Sat 2/1
6:29 pm-12:51 am
1 stop8h 22m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 2/3
8:12 am-4:50 pm
1 stop6h 38m
Punta Cana
Wed 2/12
5:04 pm-12:27 am
1 stop9h 23m
Best time to book a flight from O'Hare Intl to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from O'Hare Intl with our price prediction graph.
Travel insights for flights from O'Hare Intl to Caribbean
Get recent, data-driven insights about flights from O'Hare Intl to Caribbean including ideal travel times, pricing trends, and more.
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Caribbean?
Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean (average of $254). Flying from Chicago O'Hare Intl Airport to Caribbean in March is currently the most expensive (average of $380). 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 CB?
Find hourly flight availability from O'Hare Intl 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 January 4, 2025.
When flying from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Caribbean
Explore weekly flight availability from O'Hare Intl 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 January 4, 2025.
The most flights from ORD to 0CB are scheduled on a Monday (10 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 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 January 4, 2025.
Overall
Crew
Food
Entertainment
Boarding
Comfort
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.
Overall
Crew
Food
Entertainment
Boarding
Comfort
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.
Overall
Crew
Food
Entertainment
Boarding
Comfort
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.
Overall
Crew
Food
Entertainment
Boarding
Comfort
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.
Overall
Crew
Food
Entertainment
Boarding
Comfort
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.
Overall
Crew
Food
Entertainment
Boarding
Comfort
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 O'Hare Intl 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 O'Hare Intl to Caribbean
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
Discover the top 10 airlines that operate flights from O'Hare Intl 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 January 4, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$65 | Average$347 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$487 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$158 | Average$366 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$254 | Average$641 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$323 | Average$624 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$324 | Average$576 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$335 | Average$751 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$379 | Average$489 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$379 | Average$524 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$1,422 | Average$1,422 | FlexibilityNo cancel fee | On-time71% |