In This Issue: 

🚀 100,000 Aeroplan Points Contest

✈️ New Expansion of Air Canada Flights at Billy Bishop Airport

🔗 Prince’s Corner: 25% Off VIPorter Award Flights

🛫 Chexy Deals: Business Class to London, Vienna, & Zurich

🌍 Prince of Travel Signature Event: Toronto 2025

Flights are getting pricier, hotels aren’t getting cheaper, and travel rewards have never been more powerful. On Saturday, November 8, 2025, join the Prince of Travel team at the W Hotel in Downtown Toronto for a full day of insider tips, advanced points strategies, and networking with fellow Miles & Points enthusiasts.

From deep-dive sessions on maximizing points and luxury redemptions to curated panels, giveaways, and a VIP dinner with founder Ricky Zhang, this is your chance to level up your travel game and turn your points into unforgettable experiences.

Use code “CHEXY” to get $20 off your ticket.

💥 Chexy 100,000 Aeroplan Points Contest

Turn your everyday payments into your next getaway! For a limited time, we’re giving away 200,000 Aeroplan Points to three lucky users - including one grand prize of 100,000 points.

Whether it’s rent, utilities, or insurance, every new payment you make is another chance to win.

🎁 The Prizes

Three winners will share a total of 200,000 Aeroplan Points:

• 1st Prize: 100,000 points

• 2nd Prize: 70,000 points

• 3rd Prize: 30,000 points

Winners are selected randomly on December 12, 2025, and points will appear in your Aeroplan account within 60 days.

📝 How to Enter

Every $500 in new bill payments through Chexy = 1 contest entry. There’s no limit, which means: pay more bills, get more entries. 

You’ll also get a bonus entry for referring a friend who completes their first $500 payment. 

Example:

• $1,500 rent payment = 3 entries

• $500 car insurance = 1 entry

• Refer 2 friends = 2 bonus entries

Total = 6 chances to win!

What Can You Do With 100,000 Points?

If you win the first prize, you could get: 

• Multiple round-trip flights across North America

• Business class tickets to Europe

• Mix-and-match trips with flights, hotels, and car rentals

A single entry could be the start of your next adventure, or your entire trip if you win big.

 📚Stack Your Rewards

You can stack this contest with our other Aeroplan offers to really maximize your points: 

• For everyday users: Earn up to 5,000 Aeroplan Points when you activate your account and make your first qualifying payment. 

• For small business owners: Earn up to 100,000 Aeroplan Points on eligible business payments such as rent, taxes, or payroll.

Your new eligible payments could count towards both the contest and these bonus offers. You get double the rewards for the same bill payments! 

Ready to turn your bills into your next adventure? Start adding your bills now. 

View full contest details here. 

✈️ Air Canada Expands US Flights at Toronto’s Billy Bishop Airport

Getting to the US from downtown Toronto is about to get a lot easier. Starting Spring 2026, Air Canada will launch new non-stop flights from Billy Bishop Toronto City Airport to New York (LaGuardia), Boston, Chicago, and Washington, D.C.

Each route will run multiple times a day, making it possible to hop down for a quick day trip or weekend away, without the pain of trekking to Pearson. Here’s what you need to know: 👇

📅 The New Routes

Here’s when these new U.S. routes from Billy Bishop take off: 

• New York (LGA): March 29, 2026 - 4x daily

• Chicago (ORD): June 1, 2026 - 2x daily

• Washington D.C. (IAD): June 1, 2026 - 1x daily

• Boston (BOS): July 1, 2026 - 3x daily

Plus, Air Canada is boosting service to Montréal (9x daily) and Ottawa (6x daily) starting January 2026.

With the launch of these new routes, you can also expect:

• Fast, free Wi-Fi on board (a first for the Dash 8-400 aircraft anywhere in the world!) 

• Complimentary premium snacks, beer and wine

• Access to the Aspire Air Canada Café for eligible travellers (those with Aeroplan 50k, 75k, or Super Elite Status, or those with a premium Aeroplan co-branded credit card)

And when Billy Bishop opens US Customs Pre-Clearance next year, you’ll be able to clear customs in Toronto before boarding, meaning you’ll land in the US as a domestic passenger, with no extra hassle. 

🤔 How Many Aeroplan Points Will You Need for These Flights?

Since these are short-haul North American routes (0-500 miles), one-way award flights start at 6,000 Aeroplan points in economy. Realistically, expect pricing to be between 6,000 and 12,000 points each way, depending on demand and time of booking.

For example, we found a flight from Billy Bishop to Chicago at just 6k Aeroplan points:

And another to New York at 8.6k points:

If you do some digging, you can find economy class redemptions as low as 5.5k points one-way. 

Most of these flights don’t have business-class cabins, but it’s not really a big deal for flights under two hours. You’re better off saving your points for a long-haul business class flight overseas. 

 💳 How to Earn Points for These Flights 

Using an Aeroplan co-branded credit card on your everyday purchases, plus paying for large monthly expenses like rent and bills with Chexy, helps you earn points faster:

• Amex Aeroplan Reserve: Earn 3x points on Air Canada purchases, 2x on dining & food delivery, and 1.25x on everything else

• TD Aeroplan Visa Infinite Privilege: Earn 2x points on Air Canada purchases and 1.25x on everything else

• CIBC Aeroplan Visa Infinite Privilege: Earn 2x points on Air Canada purchases, 1.5x on gas, groceries, & dining, and 1.25x on everything else 

You can also use an American Express card and convert your Amex MR points to Aeroplan at a 1:1 ratio. Our favourites are the Amex Cobalt (earn 5x points on groceries, food, and drinks) and the Amex Platinum (earn up to 2x points with incredible travel perks). 

💡 Quick example: If you use your Amex Aeroplan Reserve to pay $2,000 in rent through Chexy each month, you’d earn about 2,543 points per month, or 30,516 points in a year. That’s enough for multiple short-haul flights, and that’s before factoring in any other spending or your welcome bonus. 

The Bottom Line

For downtown travellers, this expansion is turning Billy Bishop into a great alternative to Pearson, especially for business or quick leisure trips to the US East Coast. With free Wi-Fi, complimentary drinks and snacks, and customs pre-clearance, Air Canada’s making the short-haul experience feel a bit premium.

Fly to Europe for 25% Fewer Points

Porter Airlines has launched a limited-time VIPorter award sale, offering 25% off points redemptions on select routes. Simply book by November 6, 2025, for travel through April 30, 2026.

The discount applies to the points portion only and is automatically reflected when redeeming online. This sale covers flights with Porter Airlines, Air Transat, and Alaska Airlines, opening up travel options across North America and beyond.

One standout deal is Toronto (YYZ) to London Gatwick (LGW) for just 18,750 VIPorter points + $76 in taxes and fees.

This same flight typically costs 25,000 points or around $652 CAD in cash, meaning you’d be getting an impressive 3.1 cents per point in value — more than double our 1.5 cents per point valuation for VIPorter points at Prince of Travel.

Whether you’re planning a quick domestic trip or a transatlantic getaway, this sale stretches your balance significantly further.

And if you hold the BMO VIPorter World Elite®* Mastercard®*, you’ll enjoy even more value with perks like a free checked bag, priority check-in, and early boarding for you and up to eight companions. 

The card also earns 3x VIPorter points on Porter purchases and offers a strong welcome bonus to help you top up your account faster.

With 25% fewer points needed and the chance to combine this offer with VIPorter card perks, now’s a great time to lock in your next trip.

Check out these awesome deals you definitely don't want to miss if you're thinking about travelling in the next few months!

1. Toronto (YYZ) ➡️ Newark (EWR) ➡️ London (LHR)

   • Cost: 70,000 (Business Class)

     

   • Dates: November 27th, 2025

   • Book: Here

2. Vancouver (YVR) ➡️ Montreal (YYC) ➡️ Frankfurt (FRA) ➡️ Vienna (VEI)

   • Cost: 70,000 (Business Class)

     

   • Dates: February 08th, 2026

   • Book: Here

3. Montreal (YUL) ➡️ Zurich (ZRH)

   • Cost: 60,000 (Business Class)

     

   • Dates: December 28th, 2025

   • Book: Here