ahoyne9Welcome to the second edition of Find Flights Friday, where I guide you on booking luxury flights with points or help you find rare, affordable economy deals to top destinations.
This week, I received an alert from Thrifty Traveler about great award availability with TAP Air Portugal. Following last week’s guide on Iberia business class to Spain, this can be an option for travelers combining Portugal and Spain or looking for a round-trip to Portugal.
There are awards available through several airlines: Air Canada (60k), United (88k), Avianca (63k), and ANA (100k round-trip). Keep in mind, ANA requires booking round-trip, offering less flexibility for open-jaw travelers.
For today, I’ll focus on Air Canada, as I’ve used their platform frequently and they have a variety of credit card transfer options (Chase, Amex, Capital One, Bilt).
Air Canada’s award chart is distance-based. We are aiming for cities within the 0 – 4,000 mile range.
The first step is to see what United States based airports TAP Air Portugal flies to. To do that we will use flightconnections.com, image below. Note for my Canadian readers, both Montreal and Toronto have TAP Air Portugal flights to Lisbon and there is award availability. Flight Connections is free to use, but if you’re interested in purchasing the premium version, please consider using my affiliate link to support my work.
Next, take the list of U.S. and Canadian airports TAP Air Portugal flies to and map out their distances from Lisbon using the distance award chart. To do this, visit Calc Maps and check the distance between each city and Lisbon. For instance, the distance from Chicago to Lisbon is just under 4,000 miles, which makes it eligible for the lower award cost. The same applies to airports like Boston, Newark, New York, Washington D.C., Toronto, and Montreal.
For this letter, I’ll focus on Chicago as it’s centrally located in the U.S. and offers great access for travelers from both the U.S. and Canada, with the option for positioning flights. Start by searching for one-way flights. The best part about Air Canada is that you don’t need an account to check award availability. Simply visit their website and select the option to book with Aeroplan points to see your options.
Thanks to my premium subscription with Thrifty Traveler, finding the exact dates for award availability was much easier, avoiding the guesswork and constant clicking. For next fall, the best dates run from September 22nd to October 10th. For example, I found a flight from Chicago O’Hare (ORD) to Lisbon (LIS) on September 22nd for just 60,000 points and 78 CAD (around 57 USD). It’s a great value for flying business class to Europe.
f you’re interested in a Thrifty Traveler Premium Subscription, you can use my affiliate link to sign up and get access to the best flight deals, including award availability and low-cost flights. It’s a great resource for anyone looking to save on travel and make the most out of points and miles.
By using a simple credit card sign-up bonus from any of the major transfer partners mentioned above, you can book a one-way business class flight from Chicago to Lisbon for just 60,000 points. The value of this flight is approximately $3,450, and after accounting for taxes and fees, you’ll save nearly $350 compared to flying economy one-way. This is an incredible way to leverage points and miles for luxury travel at a fraction of the cost.
Next, you’ll want to find a return flight home. For those interested in exploring both Portugal and Spain, check out last week’s newsletter on booking business class with Iberia for as little as 35,000 points! You can fly one way to Lisbon and return from Madrid. For fall 2025, I found return availability to the U.S. between September 18th and October 10th, with a great option on October 1st. This setup offers a perfect way to explore two beautiful countries with luxury travel using points!
For a slightly higher cost in taxes and fees at 153 CAD (approx. 115 USD), you can enjoy a 10-day vacation in Portugal for just 120,000 points per person and $172 in taxes. This is a significant saving compared to economy tickets, which cost around $800 round trip.
To book positioning flights to Chicago, allow plenty of time for delays. I recommend arriving the night before or at least 6 hours before your international departure. On the return trip, I suggest a 4-hour buffer in case of delays.
How to Earn Aero Plan Points
The best way to earn Aero Plans points is through credit card partners you can certainly sign up to Aero plan’s credit card with Chase or sign up with a credit that has more flexibility. Be sure to pick a card that earns rewards with one of the transfer partners (Chase, American Express, Capital One, & Bilt).
- Capital One Venture Rewards Card
- Capital One Venture X Rewards Card
- Chase Sapphire Preferred Card
- Chase Sapphire Reserve
- American Express Gold Card
- American Express Platinum Card
Each one of these has a sign up bonus of 60,000 points or more which will be enough for your one-way flight. Be sure to check out my credit cards page for affiliate links if you’re interested in using credit card sign-up bonuses to travel luxuriously on a budget—even with a 9-5 job, it’s possible! If you have any questions or comments, feel free to leave them below. Need ideas for visiting Portugal check out my visits here. Cheers!