$308 Cheap Flights from Chicago (ORD) to Culebra (CPX)

View $308 flight on Tue, May 27, 2025Opens in a new window

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

Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Culebra (ORD-CPX)

Prices were available within the past 7 days and start at $308 for one-way flights and $631 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, May 27 - Thu, May 29
ORD
Chicago
CPX
Culebra
$631 Roundtrip, found 8 hours ago
$631
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Tue, May 27 from Chicago to Culebra, returning Thu, May 29, priced at $631 found 8 hours ago
American Airlines
Mon, May 26 - Thu, May 29
ORD
Chicago
CPX
Culebra
$635 Roundtrip, found 8 hours ago
$635
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Mon, May 26 from Chicago to Culebra, returning Thu, May 29, priced at $635 found 8 hours ago
United
Tue, May 27 - Fri, May 30
ORD
Chicago
CPX
Culebra
$645 Roundtrip, found 3 days ago
$645
Roundtrip
found 3 days ago
Select United flight, departing Tue, May 27 from Chicago to Culebra, returning Fri, May 30, priced at $645 found 3 days ago
American Airlines
Wed, May 28 - Thu, May 29
ORD
Chicago
CPX
Culebra
$645 Roundtrip, found 8 hours ago
$645
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Wed, May 28 from Chicago to Culebra, returning Thu, May 29, priced at $645 found 8 hours ago
United
Mon, May 26 - Sat, May 31
ORD
Chicago
CPX
Culebra
$649 Roundtrip, found 8 hours ago
$649
Roundtrip
found 8 hours ago
Select United flight, departing Mon, May 26 from Chicago to Culebra, returning Sat, May 31, priced at $649 found 8 hours ago
American Airlines
Tue, May 27 - Wed, Jun 4
ORD
Chicago
CPX
Culebra
$651 Roundtrip, found 8 hours ago
$651
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Tue, May 27 from Chicago to Culebra, returning Wed, Jun 4, priced at $651 found 8 hours ago
United
Sun, May 25 - Thu, May 29
ORD
Chicago
CPX
Culebra
$655 Roundtrip, found 8 hours ago
$655
Roundtrip
found 8 hours ago
Select United flight, departing Sun, May 25 from Chicago to Culebra, returning Thu, May 29, priced at $655 found 8 hours ago
American Airlines
Mon, May 26 - Wed, Jun 4
ORD
Chicago
CPX
Culebra
$655 Roundtrip, found 8 hours ago
$655
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Mon, May 26 from Chicago to Culebra, returning Wed, Jun 4, priced at $655 found 8 hours ago
JetBlue Airways
Fri, May 2 - Fri, May 9
ORD
Chicago
CPX
Culebra
$657 Roundtrip, found 6 days ago
$657
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Fri, May 2 from Chicago to Culebra, returning Fri, May 9, priced at $657 found 6 days ago
Delta
Sat, May 24 - Mon, Jun 2
ORD
Chicago
CPX
Culebra
$669 Roundtrip, found 8 hours ago
$669
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, May 24 from Chicago to Culebra, returning Mon, Jun 2, priced at $669 found 8 hours ago
Flights from Chicago (ORD) to Culebra (CPX)
Origin airport
O'Hare Intl.
Destination airport
Benjamin Rivera Noriega
Airlines serving
JetBlue Airways, United
Roundtrip price
$630
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 May. 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 $308 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?
Discover the latest flight deals from ORD to CPX by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ORD to CPX?
The cheapest flights from ORD to CPX are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to CPX?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from ORD to CPX. Sort your results by “Price (lowest to highest)” to snap up 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.

Explore a world of travel with Expedia

*Available to One Key members.