$391 Cheap Flights from Chicago (ORD) to Porto Santo (PXO)

View $391 flight on Sun, Oct 5, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Porto Santo (PXO)

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Cheap Flights from Chicago to Porto Santo (ORD-PXO)

Prices were available within the past 7 days and start at $391 for one-way flights and $590 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

TAP Portugal
Fri, Sep 26 - Wed, Oct 1
ORD
Chicago
PXO
Porto Santo
$590 Roundtrip, found 14 hours ago
$590
Roundtrip
found 14 hours ago
Select TAP Portugal flight, departing Fri, Sep 26 from Chicago to Porto Santo, returning Wed, Oct 1, priced at $590 found 14 hours ago
TAP Portugal
Mon, Aug 11 - Wed, Aug 27
ORD
Chicago
PXO
Porto Santo
$591 Roundtrip, found 6 days ago
$591
Roundtrip
found 6 days ago
Select TAP Portugal flight, departing Mon, Aug 11 from Chicago to Porto Santo, returning Wed, Aug 27, priced at $591 found 6 days ago
TAP Portugal
Fri, Sep 26 - Thu, Oct 2
ORD
Chicago
PXO
Porto Santo
$615 Roundtrip, found 14 hours ago
$615
Roundtrip
found 14 hours ago
Select TAP Portugal flight, departing Fri, Sep 26 from Chicago to Porto Santo, returning Thu, Oct 2, priced at $615 found 14 hours ago
TAP Portugal
Sun, Oct 5 - Wed, Oct 15
ORD
Chicago
PXO
Porto Santo
$616 Roundtrip, found 2 days ago
$616
Roundtrip
found 2 days ago
Select TAP Portugal flight, departing Sun, Oct 5 from Chicago to Porto Santo, returning Wed, Oct 15, priced at $616 found 2 days ago
TAP Portugal
Sun, Sep 21 - Tue, Sep 30
ORD
Chicago
PXO
Porto Santo
$616 Roundtrip, found 6 days ago
$616
Roundtrip
found 6 days ago
Select TAP Portugal flight, departing Sun, Sep 21 from Chicago to Porto Santo, returning Tue, Sep 30, priced at $616 found 6 days ago
TAP Portugal
Sun, Sep 7 - Thu, Sep 25
ORD
Chicago
PXO
Porto Santo
$641 Roundtrip, found 6 days ago
$641
Roundtrip
found 6 days ago
Select TAP Portugal flight, departing Sun, Sep 7 from Chicago to Porto Santo, returning Thu, Sep 25, priced at $641 found 6 days ago
TAP Portugal
Sun, Aug 10 - Wed, Aug 27
ORD
Chicago
PXO
Porto Santo
$727 Roundtrip, found 6 days ago
$727
Roundtrip
found 6 days ago
Select TAP Portugal flight, departing Sun, Aug 10 from Chicago to Porto Santo, returning Wed, Aug 27, priced at $727 found 6 days ago
United
Tue, Sep 23 - Tue, Sep 30
ORD
Chicago
PXO
Porto Santo
$847 Roundtrip, found 14 hours ago
$847
Roundtrip
found 14 hours ago
Select United flight, departing Tue, Sep 23 from Chicago to Porto Santo, returning Tue, Sep 30, priced at $847 found 14 hours ago
Air Canada
Sun, Sep 28 - Mon, Oct 13
ORD
Chicago
PXO
Porto Santo
$849 Roundtrip, found 6 days ago
$849
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sun, Sep 28 from Chicago to Porto Santo, returning Mon, Oct 13, priced at $849 found 6 days ago
Turkish Airlines
Sun, Sep 28 - Sun, Oct 12
ORD
Chicago
PXO
Porto Santo
$1,094 Roundtrip, found 6 days ago
$1,094
Roundtrip
found 6 days ago
Select Turkish Airlines flight, departing Sun, Sep 28 from Chicago to Porto Santo, returning Sun, Oct 12, priced at $1,094 found 6 days ago

Alternative airports near Porto Santo

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

Select flight to Porto Santo PXO. Cheapest and Closest option available. Average driving time to city center is 1 minute. Flights from $902
PXO
Porto Santo
CheapestClosest
Average driving time to city center1 min
Flights from $902
Flights from Chicago (ORD) to Porto Santo (PXO)
Origin airport
O'Hare Intl.
Destination airport
Porto Santo
Roundtrip price
$589
Distance
3855 mi

Chicago to Porto Santo Flights

The cheapest times to fly from Chicago to Porto Santo

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 Porto Santo are during the month of September. You can find some of the cheapest flights from Chicago to Porto Santo with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Porto Santo

Sunday is one of the best days to book for cheap flights from Chicago to Porto Santo: 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 Porto Santo

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 Porto Santo in 2025. You can also book with separate airlines for your outbound and return journeys, from $391 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 Porto Santo 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 Porto Santo 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 Porto Santo Airport (PXO) cost?
Discover the latest flight deals from ORD to PXO 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 PXO?
The cheapest flights from ORD to PXO 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 PXO?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from ORD to PXO. 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 Porto Santo Airport (PXO)?
Direct flights from O'Hare Intl. Airport (ORD) to Porto Santo Airport (PXO) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your travel dates and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to PXO?
Usually you'll find the largest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, this can vary based on the time of year, carrier and other factors.*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 Porto Santo Airport (PXO)?
To avoid potential delays on the O'Hare Intl. Airport (ORD) to Porto Santo Airport (PXO) route, aim to travel before 3 PM. Later flights are 22% more likely to be canceled.**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.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Porto Santo Airport (PXO) last-minute?
Last-minute fares from ORD to PXO are generally more expensive. To lock in the best rates, start searching for flights ahead of time. That being said, if you can play around with your travel dates, it's possible to score a cheap fare just before your departure.
Is it cheaper to book an ORD to PXO flight and hotel package?
Opting for an ORD to PXO flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Pick from our extensive range of accommodations and then add activities, car rentals and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Porto Santo Airport (PXO)?
Usually, it's possible to cancel or reschedule your ORD to PXO flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find further details on our Customer Service portal.

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*Available to One Key members.