$477 Cheap Flights from Chicago (ORD) to Ponta Delgada (PDL)

You can find cheap one-way flights from $477 and cheap return flights $801 Chicago, IL (ORD-O'Hare Intl.) to Ponta Delgada (PDL-Joao Paulo II) with Expedia. One-way flights generally range between $582 and $2418, and roundtrip flights usually range from $940 to $8095. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (ORD-O'Hare Intl.) to Ponta Delgada (PDL-Joao Paulo II) ticket fares go up or down.

*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.

The cheapest month to fly from ORD to PDL is October when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.

Enter ORD to PDL and your travel dates, then apply the 'Nonstop' filter to see only direct flights.

Icelandair is one of the cheapest airlines offering connecting flights from Chicago, IL (ORD-O'Hare Intl.) to Ponta Delgada (PDL-Joao Paulo II), with round-trip tickets starting from around $1,642 with a layover in Keflavik Intl. (KEF). Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.

*Prices based on flights available on Expedia in the last year.

To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Ponta Delgada (PDL-Joao Paulo II), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.

The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.

The earliest flight from Chicago O'Hare International Airport (ORD) to Ponta Delgada (PDL) typically departs at around 5:00 AM. This seasonal service is operated by American Airlines and TAP Portugal, allowing you to start your journey early and make the most of your time in the Azores. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.

The most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Ponta Delgada (PDL-Joao Paulo II) are in the evening, from 6pm to 9pm. About 31% of passengers prefer this time window. Many major carriers, including TAP Air Portugal, American Airlines, and British Airways, operate flights during this time. This timing is popular because it allows travelers to enjoy a full day in Chicago before heading off to their destination.

Flying from ORD to PDL with a connection usually takes about 12 hours, traveling roughly 3,239 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.

Business class is available on flights from ORD to PDL. Airlines that offer business class service on this route include:

• TAP Portugal
• American Airlines
• British Airways

It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Ponta Delgada (PDL-Joao Paulo II) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

From O'Hare Intl. (ORD), you can fly into Joao Paulo II (PDL) to reach Ponta Delgada. Some flights may connect through major hubs like Ronald Reagan Washington National (DCA), Philadelphia Intl. (PHL), Logan Intl. (BOS) before reaching Ponta Delgada. Compare routes and airports on Expedia to find the best flight options for your travel plans.

Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Ponta Delgada (PDL-Joao Paulo II) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.

Securing a Chicago, IL (ORD-O'Hare Intl.) to Ponta Delgada (PDL-Joao Paulo II) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.

If you booked your Chicago, IL (ORD-O'Hare Intl.) to Ponta Delgada (PDL-Joao Paulo II) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.