$522 Cheap Flights from Ponta Delgada (PDL) to Chicago (ORD)

View $522 flight on Fri, Apr 24, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $522 for one-way flights and $609 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

TAP Portugal
Sat, Jan 31 - Fri, Feb 6
PDL
São Miguel Island
ORD
Chicago
$609 Roundtrip, found 5 days ago
$609
Roundtrip
found 5 days ago
Select TAP Portugal flight, departing Sat, Jan 31 from São Miguel Island to Chicago, returning Fri, Feb 6, priced at $609 found 5 days ago
TAP Portugal
Sat, Jan 31 - Fri, Feb 6
PDL
São Miguel Island
ORD
Chicago
$616 Roundtrip, found 5 days ago
$616
Roundtrip
found 5 days ago
Select TAP Portugal flight, departing Sat, Jan 31 from São Miguel Island to Chicago, returning Fri, Feb 6, priced at $616 found 5 days ago
TAP Portugal
Sat, Jan 31 - Fri, Feb 6
PDL
São Miguel Island
ORD
Chicago
$877 Roundtrip, found 5 days ago
$877
Roundtrip
found 5 days ago
Select TAP Portugal flight, departing Sat, Jan 31 from São Miguel Island to Chicago, returning Fri, Feb 6, priced at $877 found 5 days ago
TAP Portugal
Sat, Jan 31 - Fri, Feb 6
PDL
São Miguel Island
ORD
Chicago
$884 Roundtrip, found 5 days ago
$884
Roundtrip
found 5 days ago
Select TAP Portugal flight, departing Sat, Jan 31 from São Miguel Island to Chicago, returning Fri, Feb 6, priced at $884 found 5 days ago
TAP Portugal
Sat, Jan 31 - Fri, Feb 6
PDL
São Miguel Island
ORD
Chicago
$897 Roundtrip, found 5 days ago
$897
Roundtrip
found 5 days ago
Select TAP Portugal flight, departing Sat, Jan 31 from São Miguel Island to Chicago, returning Fri, Feb 6, priced at $897 found 5 days ago
TAP Portugal
Sat, Jan 31 - Fri, Feb 6
PDL
São Miguel Island
ORD
Chicago
$904 Roundtrip, found 5 days ago
$904
Roundtrip
found 5 days ago
Select TAP Portugal flight, departing Sat, Jan 31 from São Miguel Island to Chicago, returning Fri, Feb 6, priced at $904 found 5 days ago
TAP Portugal
Sat, Jan 31 - Fri, Feb 6
PDL
São Miguel Island
ORD
Chicago
$914 Roundtrip, found 5 days ago
$914
Roundtrip
found 5 days ago
Select TAP Portugal flight, departing Sat, Jan 31 from São Miguel Island to Chicago, returning Fri, Feb 6, priced at $914 found 5 days ago
Lufthansa
Sat, Jan 31 - Fri, Feb 6
PDL
São Miguel Island
ORD
Chicago
$1,040 Roundtrip, found 5 days ago
$1,040
Roundtrip
found 5 days ago
Select Lufthansa flight, departing Sat, Jan 31 from São Miguel Island to Chicago, returning Fri, Feb 6, priced at $1,040 found 5 days ago
Air Canada
Sat, Jan 31 - Fri, Feb 6
PDL
São Miguel Island
ORD
Chicago
$1,056 Roundtrip, found 5 days ago
$1,056
Roundtrip
found 5 days ago
Select Air Canada flight, departing Sat, Jan 31 from São Miguel Island to Chicago, returning Fri, Feb 6, priced at $1,056 found 5 days ago
United
Sun, Jul 5 - Sun, Jul 12
PDL
São Miguel Island
ORD
Chicago
$1,197 Roundtrip, found 1 day ago
$1,197
Roundtrip
found 1 day ago
Select United flight, departing Sun, Jul 5 from São Miguel Island to Chicago, returning Sun, Jul 12, priced at $1,197 found 1 day ago

Frequently asked questions

How much does a flight from Joao Paulo II Airport (PDL) to O'Hare Intl. Airport (ORD) cost?
Grab a cheap one-way flight from $522 or cheap return flight from $609 from Joao Paulo II Airport (PDL) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Joao Paulo II Airport (PDL) to O'Hare Intl. Airport (ORD)?
Traveling in January may help you find better deals, as it's the cheapest month for flights between PDL and ORD. You'll typically find the lowest prices during off-peak months.
What is the cheapest airline that flies from Joao Paulo II Airport (PDL) to O'Hare Intl. Airport (ORD)?
To find the cheapest airline flying from PDL to ORD, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from Joao Paulo II Airport (PDL) to O'Hare Intl. Airport (ORD)?
There are no daily nonstop flights departing from Joao Paulo II Airport (PDL) to O'Hare Intl. Airport (ORD). But you can opt for flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be cruising above the clouds in no time.
What day of the week has the most flights from PDL to ORD?
Generally you'll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* However, this can change depending on the airline, time of year 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 Joao Paulo II Airport (PDL) to O'Hare Intl. Airport (ORD)?
To avoid possible delays on the Joao Paulo II Airport (PDL) to O'Hare Intl. Airport (ORD) route, aim to fly before 3 PM. Departures after this time have a 22% higher chance of being 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 Joao Paulo II Airport (PDL) to O'Hare Intl. Airport (ORD) last-minute?
Booking your ticket from PDL to ORD just before your getaway is typically more expensive. But if you're flexible with your travel dates and times, you could snag a cheap last-minute fare.
Is it cheaper to book a PDL to ORD flight and hotel package?
You'll typically save money by booking a PDL to ORD 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 convenient place. After choosing your ideal flights and accommodations, consider other add-ons like activities, car rentals and tours.
Can I cancel or change the date of my flight from Joao Paulo II Airport (PDL) to O'Hare Intl. Airport (ORD)?
If you reserved your PDL to ORD flight within the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of fare you have, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for further details.

Travel information

Origin airport
Joao Paulo II
Destination airport
O'Hare Intl.
Roundtrip price
$609
Distance
3238 mi

Book with confidence

Ponta Delgada to Chicago Flights

The cheapest times to fly from Ponta Delgada to Chicago

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

 

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

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

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 Ponta Delgada to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $522 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 Ponta Delgada to Chicago 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 Ponta Delgada to Chicago 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.

 

Ponta Delgada to Chicago Flights

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