If you’re a physician, dentist, pharmacist, or small business owner, you likely have large expenses that normally can’t be paid by credit card — corporate tax instalments, payroll remittances, GST/HST, professional fees.
What if those same unavoidable expenses could earn you premium flights?
That’s exactly what Chexy allows you to do.
What Is Chexy?
Chexy is a Canadian payment platform that lets you use Visa, Mastercard, or American Express to:
- Pay expenses that normally cannot be paid by credit card
- Earn points on large, one time or recurring, business expenses
Chexy charges a 1.99% fee to allow you to process business-related payments on credit card (and 1.75% for personal expenses). This is currently the lowest in the industry — lower than competitors like PaySimply and Plastiq which charge upward of 2.49%.
For professionals with high fixed expenses, that 1.99% can unlock enormous value and I’ll show you why the fee pales in comparison to the potential rewards.
What Can You Pay with Chexy?
Chexy is particularly powerful for incorporated professionals. Eligible payments include:
- Corporate tax instalments
- Payroll remittances
- GST/HST remittance
- Professional fees (e.g. CMPA)
- Other government and professional payments
If you choose to pay for personal expenses, you can use Chexy to pay for:
- Daycare or private school tuition fees
- Condominium maintainence fees
- Rent
- Utilities like hydro, gas bills
These are expenses you’re paying anyway. Chexy simply changes how you pay them to unlock rewards.
Why It Matters
Using Chexy allows you to:
1. Maximize rewards on large expenses
Large tax payments = large point balances.
2. Deduct the fee
The 1.99% fee is typically deductible as a business banking/processing fee.
3. Improve business cash flow
You gain the interest-free grace period of your credit card (often ~30-60 days).
How Chexy Works
The mechanics are simple:
- Chexy charges your credit card 3–5 business days before your payment date.
- Funds sit in your Chexy wallet (which is essentially a bank account).
- On the due date, Chexy pays the recipient via:
- Monthly PAD (Pre-Authorized Debit)
- Bank transfer
- Bill payment
The person or company or the CRA receiving the payment see the funds arrive as if it were coming from a bank chequing account. They don’t need to do anything differently to receive the funds.
You can connect up to 5 different credit cards in your Chexy wallet, allowing you to separate personal and corporate expenses.
Chexy also frequently run promotions — for example:
- “Spend an average of $10,000 for 3 months, receive 10,000 aeroplan points”
- “Spend $2,000 via Chexy and get 500 bonus Aeroplan or AMEX MR points”
The promos aren’t the primary reason to use Chexy, but they certainly are a nice bonus.
Is It Worth Paying 1.99% to Earn Points?
When I first started looking at credit cards, I was firmly against any product that charged fees if a no-fee alternative existed.
But once I understood how valuable points can be — and how they can be used strategically — the fee became much less significant of a consideration.
Let me explain.
Understanding Why Fees Can Be Worth It
Mexico during March Break
Our family of four wanted to book a March Break trip to Mexico. Being peak travel season for Canadians, the cash cost of simple economy tickets was astronomical.
Cash price for economy tickets for 4 people:
$6,400 total
If you used a no-fee, fixed value 2% cashback card like the Rogers Red World Elite Mastercard, you would need $320,000 of spending to generate $6,400 in cashback. ‘
Based on typical spending patterns for a family, that could take 6+ years to accumulate.
Instead, the same flights were booked for:
- 112,000 Flying Blue miles (which transfer from Amex Membership Rewards 1:1)
- all obtained in under 1 year
- $950 in taxes & fees
Those points came entirely from using a credit card that has an annual fee, the American Express Cobalt Card which earns:
- 5x points on groceries & dining
- 3x points on subscriptions (Youtube, Netflix etc)
- 2x points on gas
- 1x points on everything else
A family of four easily spends ~$2,000/month in the 5x categories. That’s 120,000 points in just one single year from groceries & dining alone.
Annual fee: $191
Total trip cost:
$950 (taxes) + $191 (card fee) = $1,141 instead of $6,400 cash for the flights.
Thus one redemption saved us over $5,000.
In that context, is the annual fee really significant?
Even the American Express Platinum Card with its $799 annual fee can be dwarfed by one strong redemption.
Now Let’s Apply This to Chexy
Let’s say we want to fly 2 people to Madrid in business class round trip on Iberia.
Cash price:
$8,000–$9,000
Points alternative:
- 162,000 Avios
- ~$800 in taxes/fees
Now assume we use Chexy to pay corporate taxes using the American Express Business Platinum Card, which earns 1.25 points per dollar, and for most small businesses owners, is the best card to use for Chexy.
To earn 162,000 points:
You would need to run $129,600 through the card (when compared to a 2% cash back card, this is essentially 1/3 the amount of spend required!). As many professionals and business owners know, having a tax bill of that amount every year is not unusual in Canada.
Chexy fee:
$129,600 × 1.99% = $2,579
If your marginal tax rate is ~50%, that fee is deductible, meaning the real personal cost could feel closer to ~$1,290, but we’ll use the $2,579 cost for our calculation just to be conservative.
Total out-of-pocket for the trip:
$2,579 (Chexy fee) + $800 (taxes) = $3,379
You’ve effectively spent ~$3,400 from corporate funds to fly 2 people business class round trip to Europe — a trip that would normally cost $8,000+ in personal funds (in fact, you would have had to pull out ~$16,000 from your corporation to end up with $8000 to pay for these flights).
That’s at least a $5,000 swing.
In that scenario, the 1.99% fee is absolutely worth it.
Another scenario where Chexy can make perfect sense, especially for personal expenses, is to use it to meet a minimum spend requirement to get a welcome bonus. Lets say you get the CIBC Aeroplan Visa Infinite Privilege card. The welcome bonus is typically 100,000 points, but requires a spend of $25,000 in the first 12 months to get the full points amount. If you don’t have that much to spend on your card naturally (perhaps you are using your Amex Cobalt to pay for your dining and groceries, as you should be, because of the 5x points category, so the residual natural spend you have is much less than $25K), running utility bills, tuition/daycare fees, or personal taxes through Chexy can help you hit the minimum spend requirement. Lets do the math.
$25,000 x 0.0175 (Chexy fee) = $437.50
So it cost us $437.50 to earn 100,000 aeroplan points. When used for business class flights, those 100,000 aeroplan points can easily be worth $3000 (or more). Once again, spending $437.50 to get $3000 is definitely worthwhile. Another way to do the math is to look at cents per point. Each aeroplan point earned via Chexy cost us (437.50 ÷ 100,000 x100) 0.43 cents to obtain. Aeroplan points can easily be redeemed for 2-3 cents per points (or more!). Again, the math makes it clear how worthwhile this can be even on personal expenses when used to unlock a welcome bonus.
The Bigger Picture for Professionals
For incorporated physicians and dentists especially:
- Corporate taxes
- Payroll remittances
- GST/HST
- Professional dues
These are often six-figure annual expenses.
If even a portion of those can be converted into transferable points — especially when combined with welcome bonuses — the travel upside is enormous.
Chexy simply unlocks a category of spend that was previously “dead.”
Who Is Chexy Best For?
Chexy makes the most sense if:
- You have large recurring corporate expenses
- You understand how to redeem points strategically
- You value premium cabin travel
- You can pay your card in full and avoid interest
It is not ideal if:
- You carry balances
- You redeem points at low value (e.g., statement credit)
Final Thoughts
When you only look at the 1.99% fee, Chexy might seem unnecessary.
But when you zoom out and view it through the lens of:
- Business tax deductibility
- Premium flight redemptions
- Six-figure annual expenses
- Transferable points currencies
It becomes a powerful tool.
For professionals who already understand points strategy, Chexy can convert unavoidable corporate obligations into unforgettable travel experiences.
And in that context, the fee becomes very small.
If you want help deciding whether Chexy makes sense for your situation — or how to pair it with the right credit cards — please feel free to reach out. The strategy matters just as much as the tool.
If you’re convinced, sign up for a free Chexy account and read my how-to article for a step-by-step guide to setting up corporate tax payments through Chexy.
Referrals
If you found this article helpful, please consider using one of my referral links to support the work I do. It costs you nothing extra and by using a referral you are often able to get elevated sign-up bonuses, access to points promotions, or a discount. Most importantly, this helps convince my wife that the hours I spend on this hobby are worth it!
For Amex credit cards earning Membership Rewards, the most powerful and flexible travel points in Canada, like the Cobalt, Gold, Business Gold, Platinum, and Business Platinum please reach out to learn about the best sign up bonus options.
If you shop a lot (>$550 month) at Costco and are interested in flying to Europe, the Brim Flying Blue Mastercard is a solid choice and can be applied for using this link.
After your flight is sorted out, you’ll need a hotel room. For Amex credit cards that earn Marriott Bonvoy points such as the Marriott Bonvoy Amex and Marriott Bonvoy Business Amex, please reach out to learn about the best sign up bonus options.
To supercharge your points earning, use Chexy via this link to pay for things like rent, taxes, professional fees and other expenses that normally cannot go on a credit card.
Once you have accumulated points, you will need to search for flight redemptions efficiently. Roame is the best tool to quickly search multiple programs, multiple destinations, across many dates. Please use the following link and use code PP10 for 10% off the Friends of Roame subscription.
If you are new to points and rewards and want to learn more about optimization and have a personalized approach, please reach out to me for a free one-on-one consultation.
