$432 Cheap Flights from Chicago (MDW) to Culebra (CPX)

View $432 flight on Wed, Apr 1, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Culebra (CPX-Benjamin Rivera Noriega)

Cheap Flights from Chicago to Culebra (MDW-CPX)

Prices were available within the past 7 days and start at $432 for one-way flights and $1,034 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Dec 10 - Wed, Dec 17
MDW
Chicago
CPX
Culebra
$1,034 Roundtrip, found 6 days ago
$1,034
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Dec 10 from Chicago to Culebra, returning Wed, Dec 17, priced at $1,034 found 6 days ago
Delta
Wed, Dec 10 - Wed, Dec 17
MDW
Chicago
CPX
Culebra
$1,054 Roundtrip, found 6 days ago
$1,054
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Dec 10 from Chicago to Culebra, returning Wed, Dec 17, priced at $1,054 found 6 days ago
Delta
Mon, Oct 27 - Wed, Oct 29
MDW
Chicago
CPX
Culebra
$1,062 Roundtrip, found 12 hours ago
$1,062
Roundtrip
found 12 hours ago
Select Delta flight, departing Mon, Oct 27 from Chicago to Culebra, returning Wed, Oct 29, priced at $1,062 found 12 hours ago
Delta
Mon, Oct 27 - Thu, Oct 30
MDW
Chicago
CPX
Culebra
$1,087 Roundtrip, found 1 day ago
$1,087
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Oct 27 from Chicago to Culebra, returning Thu, Oct 30, priced at $1,087 found 1 day ago
Delta
Wed, Apr 1 - Sat, Apr 11
MDW
Chicago
CPX
Culebra
$1,265 Roundtrip, found 4 hours ago
$1,265
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Apr 1 from Chicago to Culebra, returning Sat, Apr 11, priced at $1,265 found 4 hours ago
Delta
Fri, Jan 16 - Mon, Jan 19
MDW
Chicago
CPX
Culebra
$1,270 Roundtrip, found 1 day ago
$1,270
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jan 16 from Chicago to Culebra, returning Mon, Jan 19, priced at $1,270 found 1 day ago
Delta
Wed, Apr 1 - Sat, Apr 11
MDW
Chicago
CPX
Culebra
$1,285 Roundtrip, found 4 hours ago
$1,285
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Apr 1 from Chicago to Culebra, returning Sat, Apr 11, priced at $1,285 found 4 hours ago
Delta
Fri, Jan 16 - Mon, Jan 19
MDW
Chicago
CPX
Culebra
$1,305 Roundtrip, found 4 days ago
$1,305
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Jan 16 from Chicago to Culebra, returning Mon, Jan 19, priced at $1,305 found 4 days ago
Delta
Wed, Apr 1 - Sat, Apr 11
MDW
Chicago
CPX
Culebra
$1,362 Roundtrip, found 4 days ago
$1,362
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Apr 1 from Chicago to Culebra, returning Sat, Apr 11, priced at $1,362 found 4 days ago
Delta
Wed, Apr 1 - Sat, Apr 11
MDW
Chicago
CPX
Culebra
$1,370 Roundtrip, found 2 days ago
$1,370
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Apr 1 from Chicago to Culebra, returning Sat, Apr 11, priced at $1,370 found 2 days ago
Delta
Wed, Apr 1 - Sat, Apr 11
MDW
Chicago
CPX
Culebra
$1,390 Roundtrip, found 2 days ago
$1,390
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Apr 1 from Chicago to Culebra, returning Sat, Apr 11, priced at $1,390 found 2 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 $819
STT
Cyril E. King
Cheapest
Flights from $819
Select flight to Antonio Rivera Rodriguez VQS. Average driving time to city center is 1 hour 57 minutes. Flights from $1,195
VQS
Antonio Rivera Rodriguez
Average driving time to city center1 h 57 min
Flights from $1,195

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Benjamin Rivera Noriega Airport (CPX) cost?
Lock in a cheap one-way flight from $432 or cheap return flight from $1,034 from Midway Intl. Airport (MDW) to Benjamin Rivera Noriega Airport (CPX) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Benjamin Rivera Noriega Airport (CPX)?
The cheapest month to fly from MDW to CPX is December, when there's less demand. Off-peak months are often when you'll find cheap fares for travel between these airports.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Benjamin Rivera Noriega Airport (CPX)?
Use the filter tool on Expedia to compare different airlines and find the most affordable carrier that'll fly you from MDW to CPX. Then, sort your results by "Price (lowest to highest)" to snag a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Benjamin Rivera Noriega Airport (CPX)?
You'll need to hop on a flight with a layover when traveling from Midway Intl. Airport (MDW) to Benjamin Rivera Noriega Airport (CPX). There are no daily direct flights on this route. However, simply filter your search to include one or two stops to find the best option for your trip.
What day of the week has the most flights from MDW to CPX?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Just remember that flight schedules can vary based 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 Midway Intl. Airport (MDW) to Benjamin Rivera Noriega Airport (CPX)?
To avoid potential delays on the Midway Intl. Airport (MDW) to Benjamin Rivera Noriega Airport (CPX) route, aim to travel before 3 PM. Flights after this time have a 22% higher chance of cancellation.**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 Midway Intl. Airport (MDW)?
Browse your flight options from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU). This is the only Culebra airport you can jet into if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Benjamin Rivera Noriega Airport (CPX) last-minute?
Last-minute bookings from MDW to CPX are generally more expensive. For the best rates, start searching for flights as soon as possible. That being said, if your travel plans are flexible, you may score a cheap ticket just before your departure.
Is it cheaper to book a MDW to CPX flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to CPX flight and hotel package with Expedia could result in significant savings. What's more, having everything in one place will take the hassle out of travel planning. Simply secure your flights and select from our extensive range of hotels, then customize your trip with extras like car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Benjamin Rivera Noriega Airport (CPX)?
If you reserved your MDW to CPX flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you'd like more information.

Travel information

Origin airport
Midway Intl.
Destination airport
Benjamin Rivera Noriega
Roundtrip price
$1,034
Distance
2091 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 December. 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 $432 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.