$276 Cheap Flights from Chicago (ORD) to Culebra (CPX)

View $276 flight on Mon, Feb 23, 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 $276 for one-way flights and $577 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sun, Feb 22 - Tue, Feb 24
ORD
Chicago
CPX
Culebra
$577 Roundtrip, found 1 day ago
$577
Roundtrip
found 1 day ago
Select United flight, departing Sun, Feb 22 from Chicago to Culebra, returning Tue, Feb 24, priced at $577 found 1 day ago
United
Sat, Feb 21 - Tue, Feb 24
ORD
Chicago
CPX
Culebra
$581 Roundtrip, found 1 day ago
$581
Roundtrip
found 1 day ago
Select United flight, departing Sat, Feb 21 from Chicago to Culebra, returning Tue, Feb 24, priced at $581 found 1 day ago
JetBlue Airways
Mon, Mar 30 - Fri, Apr 17
ORD
Chicago
CPX
Culebra
$585 Roundtrip, found 1 day ago
$585
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Mar 30 from Chicago to Culebra, returning Fri, Apr 17, priced at $585 found 1 day ago
United
Mon, Jan 12 - Thu, Jan 29
ORD
Chicago
CPX
Culebra
$597 Roundtrip, found 1 day ago
$597
Roundtrip
found 1 day ago
Select United flight, departing Mon, Jan 12 from Chicago to Culebra, returning Thu, Jan 29, priced at $597 found 1 day ago
United
Sun, Feb 1 - Thu, Feb 19
ORD
Chicago
CPX
Culebra
$601 Roundtrip, found 1 day ago
$601
Roundtrip
found 1 day ago
Select United flight, departing Sun, Feb 1 from Chicago to Culebra, returning Thu, Feb 19, priced at $601 found 1 day ago
JetBlue Airways
Sun, Feb 1 - Fri, Feb 6
ORD
Chicago
CPX
Culebra
$604 Roundtrip, found 6 days ago
$604
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sun, Feb 1 from Chicago to Culebra, returning Fri, Feb 6, priced at $604 found 6 days ago
American Airlines
Mon, Feb 16 - Tue, Mar 3
ORD
Chicago
CPX
Culebra
$606 Roundtrip, found 1 day ago
$606
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Feb 16 from Chicago to Culebra, returning Tue, Mar 3, priced at $606 found 1 day ago
United
Sat, Dec 6 - Tue, Dec 16
ORD
Chicago
CPX
Culebra
$607 Roundtrip, found 1 day ago
$607
Roundtrip
found 1 day ago
Select United flight, departing Sat, Dec 6 from Chicago to Culebra, returning Tue, Dec 16, priced at $607 found 1 day ago
American Airlines
Mon, Feb 23 - Fri, Feb 27
ORD
Chicago
CPX
Culebra
$608 Roundtrip, found 5 hours ago
$608
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Mon, Feb 23 from Chicago to Culebra, returning Fri, Feb 27, priced at $608 found 5 hours ago
United
Wed, Jan 28 - Fri, Feb 13
ORD
Chicago
CPX
Culebra
$614 Roundtrip, found 1 day ago
$614
Roundtrip
found 1 day ago
Select United flight, departing Wed, Jan 28 from Chicago to Culebra, returning Fri, Feb 13, priced at $614 found 1 day 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 $673
STT
Cyril E. King
Cheapest
Flights from $673
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
Flights from Chicago (ORD) to Culebra (CPX)
Origin airport
O'Hare Intl.
Destination airport
Benjamin Rivera Noriega
Airlines serving
JetBlue Airways, United
Roundtrip price
$576
Distance
2106 mi

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 February. 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 $276 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.

 

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 $276 or cheap return flight from $577 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 February 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.

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*Available to One Key members.