$268 Cheap Flights from Chicago (ORD) to Culebra (CPX)

View $268 flight on Tue, Jan 20, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Culebra (CPX-Benjamin Rivera Noriega)

Cheap Flights from Chicago to Culebra (ORD-CPX)

Prices were available within the past 7 days and start at $268 for one-way flights and $515 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Wed, Apr 15 - Fri, Apr 24
ORD
Chicago
CPX
Culebra
$515 Roundtrip, found 3 days ago
$515
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Apr 15 from Chicago to Culebra, returning Fri, Apr 24, priced at $515 found 3 days ago
United
Mon, Jan 12 - Fri, Jan 23
ORD
Chicago
CPX
Culebra
$541 Roundtrip, found 1 day ago
$541
Roundtrip
found 1 day ago
Select United flight, departing Mon, Jan 12 from Chicago to Culebra, returning Fri, Jan 23, priced at $541 found 1 day ago
United
Sun, Jan 18 - Fri, Jan 23
ORD
Chicago
CPX
Culebra
$545 Roundtrip, found 1 day ago
$545
Roundtrip
found 1 day ago
Select United flight, departing Sun, Jan 18 from Chicago to Culebra, returning Fri, Jan 23, priced at $545 found 1 day ago
United
Mon, Jan 12 - Wed, Jan 21
ORD
Chicago
CPX
Culebra
$561 Roundtrip, found 1 day ago
$561
Roundtrip
found 1 day ago
Select United flight, departing Mon, Jan 12 from Chicago to Culebra, returning Wed, Jan 21, priced at $561 found 1 day ago
JetBlue Airways
Tue, Apr 14 - Fri, Apr 24
ORD
Chicago
CPX
Culebra
$563 Roundtrip, found 3 days ago
$563
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Apr 14 from Chicago to Culebra, returning Fri, Apr 24, priced at $563 found 3 days ago
American Airlines
Wed, Jan 14 - Thu, Jan 22
ORD
Chicago
CPX
Culebra
$565 Roundtrip, found 1 day ago
$565
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jan 14 from Chicago to Culebra, returning Thu, Jan 22, priced at $565 found 1 day ago
United
Sun, Jan 18 - Wed, Jan 21
ORD
Chicago
CPX
Culebra
$565 Roundtrip, found 1 day ago
$565
Roundtrip
found 1 day ago
Select United flight, departing Sun, Jan 18 from Chicago to Culebra, returning Wed, Jan 21, priced at $565 found 1 day ago
JetBlue Airways
Wed, Apr 15 - Wed, Apr 22
ORD
Chicago
CPX
Culebra
$585 Roundtrip, found 3 days ago
$585
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Apr 15 from Chicago to Culebra, returning Wed, Apr 22, priced at $585 found 3 days ago
United
Mon, Feb 9 - Fri, Feb 20
ORD
Chicago
CPX
Culebra
$606 Roundtrip, found 3 days ago
$606
Roundtrip
found 3 days ago
Select United flight, departing Mon, Feb 9 from Chicago to Culebra, returning Fri, Feb 20, priced at $606 found 3 days ago
JetBlue Airways
Tue, Apr 14 - Mon, Apr 27
ORD
Chicago
CPX
Culebra
$611 Roundtrip, found 3 days ago
$611
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Apr 14 from Chicago to Culebra, returning Mon, Apr 27, priced at $611 found 3 days ago

Alternative airports near Culebra

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Cyril E. King STT. Cheapest option available. Flights from $459
STT
Cyril E. King
Cheapest
Flights from $459
Select flight to Antonio Rivera Rodriguez VQS. Average driving time to city center is 1 hour 57 minutes. Flights from $794
VQS
Antonio Rivera Rodriguez
Average driving time to city center1 h 57 min
Flights from $794

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Benjamin Rivera Noriega Airport (CPX) cost?
Snag a cheap one-way flight from $268 or cheap return flight from $515 from O'Hare Intl. Airport (ORD) to Benjamin Rivera Noriega Airport (CPX) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Benjamin Rivera Noriega Airport (CPX)?
Flying in April is a great way to save, as it's the cheapest month for flights between ORD and CPX. You'll usually find the lowest fares during the off-season.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Benjamin Rivera Noriega Airport (CPX)?
Use the filter tool on Expedia to compare different airlines and find the most affordable carrier that'll take you from ORD to CPX. Then, sort your results by "Price (lowest to highest)" to snag a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to Benjamin Rivera Noriega Airport (CPX)?
Direct flights from O'Hare Intl. Airport (ORD) to Benjamin Rivera Noriega Airport (CPX) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel details and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to CPX?
Friday is usually the busiest day for flights, while Tuesday is often the quietest.* Keep in mind that flight schedules can vary depending on a range of factors, such as the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Benjamin Rivera Noriega Airport (CPX)?
To touch down at Benjamin Rivera Noriega Airport (CPX) on schedule, select a flight that leaves from O'Hare Intl. Airport (ORD) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Culebra from O'Hare Intl. Airport (ORD)?
Explore your flight options from O'Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU). This is the only airport in Culebra you can land at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Benjamin Rivera Noriega Airport (CPX) last-minute?
Last-minute bookings from ORD to CPX are typically more expensive. To lock in the best prices, start searching for flights as early as possible. That said, if your travel plans are flexible, you may find a cheap fare right before you leave.
Is it cheaper to book an ORD to CPX flight and hotel package?
You'll generally save money by securing an ORD to CPX flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. Once you've selected your ideal accommodations and flights, consider adding extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Benjamin Rivera Noriega Airport (CPX)?
Typically, it's possible to reschedule or cancel your ORD to CPX flight. However, if it's been more than 24 hours since booking, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Benjamin Rivera Noriega
Airlines serving
JetBlue Airways, United
Roundtrip price
$515
Distance
2106 mi

Book with confidence

Chicago to Culebra Flights

The cheapest times to fly from Chicago to Culebra

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Culebra are during the month of April. You can find some of the cheapest flights from Chicago to Culebra with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Culebra

Sunday is one of the best days to book for cheap flights from Chicago to Culebra: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Culebra

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Culebra in 2025. You can also book with separate airlines for your outbound and return journeys, from $268 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Culebra flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Culebra airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Culebra Flights

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*Available to One Key members.