$344 Cheap Flights from Chicago (ORD) to Ponta Delgada (PDL)

View $344 flight on Tue, Feb 17, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Joao Paulo II Airport (PDL)

Cheap Flights from Chicago to Ponta Delgada (ORD-PDL)

Prices were available within the past 7 days and start at $344 for one-way flights and $551 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

TAP Portugal
Wed, Apr 8 - Wed, Apr 15
ORD
Chicago
PDL
São Miguel Island
$551 Roundtrip, found 1 hour ago
$551
Roundtrip
found 1 hour ago
Select TAP Portugal flight, departing Wed, Apr 8 from Chicago to São Miguel Island, returning Wed, Apr 15, priced at $551 found 1 hour ago
TAP Portugal
Sun, Nov 9 - Tue, Nov 18
ORD
Chicago
PDL
São Miguel Island
$558 Roundtrip, found 4 hours ago
$558
Roundtrip
found 4 hours ago
Select TAP Portugal flight, departing Sun, Nov 9 from Chicago to São Miguel Island, returning Tue, Nov 18, priced at $558 found 4 hours ago
TAP Portugal
Sun, Mar 8 - Sat, Mar 21
ORD
Chicago
PDL
São Miguel Island
$571 Roundtrip, found 1 day ago
$571
Roundtrip
found 1 day ago
Select TAP Portugal flight, departing Sun, Mar 8 from Chicago to São Miguel Island, returning Sat, Mar 21, priced at $571 found 1 day ago
TAP Portugal
Sun, Feb 1 - Sat, Feb 7
ORD
Chicago
PDL
São Miguel Island
$578 Roundtrip, found 2 days ago
$578
Roundtrip
found 2 days ago
Select TAP Portugal flight, departing Sun, Feb 1 from Chicago to São Miguel Island, returning Sat, Feb 7, priced at $578 found 2 days ago
TAP Portugal
Wed, Apr 22 - Thu, Apr 30
ORD
Chicago
PDL
São Miguel Island
$581 Roundtrip, found 1 day ago
$581
Roundtrip
found 1 day ago
Select TAP Portugal flight, departing Wed, Apr 22 from Chicago to São Miguel Island, returning Thu, Apr 30, priced at $581 found 1 day ago
TAP Portugal
Wed, Dec 31 - Thu, Jan 29
ORD
Chicago
PDL
São Miguel Island
$588 Roundtrip, found 2 days ago
$588
Roundtrip
found 2 days ago
Select TAP Portugal flight, departing Wed, Dec 31 from Chicago to São Miguel Island, returning Thu, Jan 29, priced at $588 found 2 days ago
United
Sat, Aug 15 - Sat, Aug 22
ORD
Chicago
PDL
São Miguel Island
$875 Roundtrip, found 6 days ago
$875
Roundtrip
found 6 days ago
Select United flight, departing Sat, Aug 15 from Chicago to São Miguel Island, returning Sat, Aug 22, priced at $875 found 6 days ago
Turkish Airlines
Mon, Mar 9 - Mon, Mar 16
ORD
Chicago
PDL
São Miguel Island
$1,216 Roundtrip, found 4 days ago
$1,216
Roundtrip
found 4 days ago
Select Turkish Airlines flight, departing Mon, Mar 9 from Chicago to São Miguel Island, returning Mon, Mar 16, priced at $1,216 found 4 days ago
Iberia
Mon, Jun 1 - Mon, Jun 8
ORD
Chicago
PDL
São Miguel Island
$1,543 Roundtrip, found 4 days ago
$1,543
Roundtrip
found 4 days ago
Select Iberia flight, departing Mon, Jun 1 from Chicago to São Miguel Island, returning Mon, Jun 8, priced at $1,543 found 4 days ago
British Airways
Fri, Apr 10 - Sat, Apr 18
ORD
Chicago
PDL
São Miguel Island
$1,981 Roundtrip, found 18 hours ago
$1,981
Roundtrip
found 18 hours ago
Select British Airways flight, departing Fri, Apr 10 from Chicago to São Miguel Island, returning Sat, Apr 18, priced at $1,981 found 18 hours ago

Find the cheapest month to fly from Chicago (ORD) to Ponta Delgada (PDL)

September is typically the cheapest month to fly

From $549 - $1,233 per traveler.

Alternative airports near Ponta Delgada

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

Select flight to Joao Paulo II PDL. Cheapest option available. Flights from $601
PDL
Joao Paulo II
Cheapest
Flights from $601

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Joao Paulo II Airport (PDL) cost?
Grab a cheap one-way flight from $344 or cheap return flight from $551 from O'Hare Intl. Airport (ORD) to Joao Paulo II Airport (PDL) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Joao Paulo II Airport (PDL)?
The cheapest month to fly from ORD to PDL is April, when there's less demand. Off-peak season is typically when better flight deals are available between these airports.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Joao Paulo II Airport (PDL)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Select your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest ORD to PDL flight.
How many flights per day from O'Hare Intl. Airport (ORD) to Joao Paulo II Airport (PDL)?
Nonstop flights from O'Hare Intl. Airport (ORD) to Joao Paulo II Airport (PDL) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel details and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to PDL?
You'll typically find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*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 Joao Paulo II Airport (PDL)?
Select a flight from O'Hare Intl. Airport (ORD) to Joao Paulo II Airport (PDL) that takes off before 3 PM to reduce the risk of cancellations. Departures after this hour are on average 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 Joao Paulo II Airport (PDL) last-minute?
Waiting until just before your trip to book your flight from ORD to PDL generally means paying more. While you might find some last-minute offers, there's no guarantee. Keep your travel plans flexible to boost your chances of getting a bargain.
Is it cheaper to book an ORD to PDL flight and hotel package?
You'll typically save money by booking an ORD to PDL flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. Once you've selected your ideal accommodations and flights, you can add extras such as activities, tours and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Joao Paulo II Airport (PDL)?
In most instances, you can reschedule or cancel your ORD to PDL flight. However, there may be additional fees, especially if you made your booking more than 24 hours ago. Double-check your itinerary for the airline's fees and rules on flight changes, or if you need further information, head to our Customer Service portal.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Joao Paulo II
Airlines serving
British Airways, Lufthansa, Swiss International Air Lines, TAP Portugal, Turkish Airlines
Roundtrip price
$551
Distance
3238 mi

Book with confidence

Chicago to Ponta Delgada Flights

The cheapest times to fly from Chicago to Ponta Delgada

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

 

The best time to book a flight from Chicago to Ponta Delgada

Sunday is one of the best days to book for cheap flights from Chicago to Ponta Delgada: 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 Ponta Delgada

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 Ponta Delgada in 2025. You can also book with separate airlines for your outbound and return journeys, from $344 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 Ponta Delgada 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 Ponta Delgada 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 Ponta Delgada Flights

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*Available to One Key members.