$117+ Cheap flights from Caribbean to O'Hare Intl (ORD)
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 7/17. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Caribbean to O'Hare Intl 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 O'Hare Intl
Keep the following information in mind while searching for Caribbean to O'Hare Intl flight deals. Data was last updated June 12, 2025.
Round-trip from | $191 (Booking.com) |
|---|---|
One-way from | $117 (SmartFares) |
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 O'Hare Intl
Cheapest flights from Caribbean to O'Hare IntlExplore the most affordable flight options available from Caribbean to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
Explore the most affordable flight options available from Caribbean to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 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 6/12. 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 Cheapflightsfares deal was found by Cheapflights users on 6/9. 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 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 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 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.
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This SmartFares 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 SmartFares 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 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 CheapOair 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.
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean to O'Hare Intl 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 June 12, 2025.
Use the filters below to find and compare flights from Caribbean to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 7/15
3:50 pm-11:13 pm
1 stop8h 23m
Chicago O'Hare Intl
Tue 7/22
5:05 am-3:30 pm
1 stop9h 25m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 9/5
3:40 am-2:53 pm
1 stop12h 13m
Chicago O'Hare Intl
Thu 9/11
6:20 am-11:58 pm
1 stop16h 38m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 6/26
8:24 pm-8:50 am
1 stop13h 26m
Chicago O'Hare Intl
Thu 8/28
6:35 am-11:54 pm
1 stop16h 19m
Saint Thomas IslandChicago
STT - ORD
STTORD
Saint Thomas Island Cyril E King
Wed 7/2
1:24 pm-8:23 pm
1 stop7h 59m
Chicago O'Hare Intl
Tue 7/15
5:40 pm-9:48 am
1 stop15h 08m
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Wed 7/9
3:31 pm-7:36 pm
Nonstop5h 05m
Chicago O'Hare Intl
Wed 8/13
8:34 pm-11:05 am
1 stop13h 31m
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Wed 7/23
12:10 pm-11:13 pm
1 stop11h 03m
Chicago O'Hare Intl
Sat 8/2
5:38 pm-9:53 am
1 stop16h 15m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 11/12
6:01 am-3:08 pm
1 stop11h 07m
Chicago O'Hare Intl
Wed 11/19
4:05 pm-2:45 am
1 stop8h 40m
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Tue 8/5
4:35 pm-4:46 pm
1 stop25h 11m
Chicago O'Hare Intl
Tue 8/26
12:50 pm-12:40 pm
1 stop22h 50m
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Fri 6/27
2:23 pm-7:00 pm
Nonstop4h 37m
Chicago O'Hare Intl
Mon 6/30
8:44 am-12:42 pm
Nonstop3h 58m
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Tue 8/19
3:29 pm-9:55 am
1 stop19h 26m
Chicago O'Hare Intl
Wed 8/27
5:05 am-2:34 pm
1 stop8h 29m
Best time to book a flight from Caribbean to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Caribbean with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Caribbean to Chicago O'Hare Intl Airport
What is the cheapest month to book a flight from Caribbean to Chicago O'Hare Intl Airport?
Currently, August is the cheapest month in which you can book a flight from Caribbean to Chicago O'Hare Intl Airport (average of $245). Flying from Caribbean to Chicago O'Hare Intl Airport 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 ORD?
Find hourly flight availability from Caribbean to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.
When flying from Caribbean to Chicago O'Hare Intl Airport, 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 Chicago O'Hare Intl Airport
Explore weekly flight availability from Caribbean to O'Hare Intl. 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 June 12, 2025.
The most flights from 0CB to ORD 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 O'Hare Intl by month
Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago O'Hare Intl Airport 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 Chicago O'Hare Intl Airport when rainfall is around 1.7 in.
Temperature in O'Hare Intl by month
Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago O'Hare Intl Airport, 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 O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated June 12, 2025.
Food
Boarding
Comfort
Overall
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Comfort
Overall
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Comfort
Overall
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Comfort
Overall
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Comfort
Overall
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Comfort
Overall
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
Related info for your journey
Find useful and relevant information for your journey from Caribbean to O'Hare Intl. 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 Caribbean to O'Hare Intl
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Caribbean to O'Hare Intl
Discover the top 6 airlines that operate flights from Caribbean to O'Hare Intl. 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 June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$326 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$137 | Average$322 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$172 | Average$473 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$217 | Average$528 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$257 | Average$431 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$329 | Average$558 | FlexibilityNo cancel fee | On-time71% |