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Chexy lets you charge certain business expenses to a credit card, even when the provider doesn’t accept cards directly, so you can earn points on them. For many entrepreneurs, the expenses their business needs to run also become a chance to earn thousands of points and unlock some of the best welcome offers from business credit cards faster, through Chexy Business.
Here’s how to calculate the real cost of this strategy, factoring in service fees and the potential tax impact, plus the best American Express Business cards to pair with Chexy.
Business expenses can add up to significant amounts quickly. Tax instalments and GST/QST remittances alone can reach several thousand dollars a year. Then come supplier fees and operating costs on top of that.
Yet most of these expenses usually earn no rewards at all when paid directly from a bank account.
That’s why some small business owners use solutions like Chexy to pay certain expenses with a credit card and earn rewards. In some cases, this strategy can even get you points at a lower cost than buying them directly from a loyalty program.
This strategy becomes especially interesting when combined with business credit cards offering generous welcome offers, such as several American Express Business cards.
Chexy is a Canadian platform that lets you pay certain expenses that normally aren’t accepted by credit card. In exchange for a service fee, Chexy makes the payment on the client’s behalf using an eligible payment method. The user can then charge the transaction to their credit card and earn the associated rewards.
Chexy charges a service fee of 1.75% per transaction for Canadian credit cards (Visa and American Express), and 2.5% for international cards. For a consumer who just wants points, those fees can seem high. For a business that already needs to make large payments, though, the math can look different.
For a full overview of the platform, see our complete guide to Chexy as well as our article on Chexy for small businesses, which covers the sign-up and account verification steps in detail.
One of the main benefits for businesses using Chexy is that it covers certain expenses that generally can’t be paid by credit card. Eligible payments change over time and depend on the services Chexy offers as well as the recipient’s eligibility.
Among the business expenses that may be eligible, you’ll find:
Before making a payment, we recommend checking directly with Chexy whether the expense you want to pay is eligible.
Tax instalments alone often represent a major cash outflow for many self-employed workers and business owners.
Take the example of an entrepreneur who needs to pay $25,000 in tax instalments over a year, paid through Chexy with a card like the American Express Aeroplan Business Reserve Card.
The basic math, before any tax impact, is the same regardless of your business structure:
*31,250 points come from the initial payment ($25,000 × 1.25 points). About 547 additional points come from the Chexy fee ($437.50 × 1.25 points), based on the earn rate of the card used. In this case, the American Express Aeroplan Business Reserve Card earns 1.25 Aeroplan points per dollar on everyday purchases.
At this stage, the gross cost is about 1.38¢ per point, no matter who pays the bill, a self-employed worker or an incorporated business. It’s only once you factor in the potential tax impact that the paths diverge, and that’s where you need to be careful.
If the service fees turned out to be deductible for your business, part of the cost could be offset by a tax saving, but that saving varies a lot depending on your structure. For a corporation eligible for the small business deduction (SBD), the combined tax rate applicable to eligible income sits at about 11.2% for tax years starting after April 29, 2026, a drop from the previous 12.2% rate. A corporation that doesn’t meet the provincial 5,500-paid-hours test, but still qualifies for the federal deduction, instead lands at a combined rate of about 20.5%. Beyond the $500,000 eligible income limit, or for a corporation not eligible for the SBD, the general combined rate is about 26.5%.
Either way, the potential tax saving remains secondary: it would improve the return, but it isn’t the reason the strategy is worth it, since the business already needs to make the real $25,000 expense regardless. Confirm your specific situation with a tax professional before assuming any portion of the Chexy fees will be deductible.
To measure Chexy’s advantage, let’s compare its cost per point to buying Aeroplan points directly. At the regular price of 3.75¢ per point, getting 31,797 points would cost about $1,192 before tax, with no bonus at all.
Unlike the service fees tied to a real business expense, buying Aeroplan points for personal use isn’t a deductible business expense. Even leaving aside any potential tax deduction, Chexy’s fees stay below the cost of buying an equivalent number of points directly, even at the best promotion of the year.
Our Aeroplan point value estimate sits at 2¢, which confirms the advantage of the Chexy strategy in this example.
Before adding Chexy to your points strategy, here are a few things to check so interest charges or an administrative surprise don’t wipe out the advantage you gained.
Beyond earning points, Chexy can also become an excellent tool for hitting the spending thresholds required by the best travel credit cards.
Cards with the most generous welcome offers often require several thousand dollars in spending within the first few months after opening the account. For many individuals, those thresholds can be hard to reach.
Entrepreneurs, however, have a real advantage: they often have business expenses they need to pay anyway. Whether it’s tax instalments, government remittances, or supplier payments, these expenses can help unlock a welcome offer much faster. Even with service fees applied, the value of a welcome offer can far outweigh the cost of the transaction.
The best choice depends mainly on your travel goals and the type of rewards you want to earn. Depending on the credit card you use, business expenses paid through Chexy can help you earn different types of rewards.
The Business Platinum Card from American Express is aimed at entrepreneurs looking for maximum flexibility. If you haven’t decided which rewards program to prioritize yet, Membership Rewards points are probably the most flexible option: the card earns 1.25 Membership Rewards points per dollar on expenses charged through Chexy.
Unlike points tied to a single loyalty program, Membership Rewards points can be held until you’re ready to book your trip, then converted to whichever program offers the best value for your destination. They can notably be transferred to:
For an entrepreneur who generates a significant volume of spending each year, this flexibility lets you build up a sizable reserve of points while keeping a lot of freedom when planning your trips. Its generous welcome offer is also one of the card’s biggest draws: business expenses paid through Chexy can help you hit the required spending threshold quickly.
The American Express Business Gold Rewards Card is an appealing option for entrepreneurs who want to earn Membership Rewards points while paying a more accessible annual fee than the Business Platinum Card. Eligible expenses paid through Chexy can also help you hit the spending threshold required for its welcome offer.
This card is especially appealing for entrepreneurs who travel regularly with Air Canada and its partners, thanks in part to travel perks like Maple Leaf Lounge access and free baggage on Air Canada.
Your business expenses can help you earn Aeroplan points quickly. For an entrepreneur with few opportunities to earn Aeroplan points through everyday spending, Chexy can be an especially valuable opportunity. These points can then be used for flights within Canada and internationally, notably in business class, where their value is often highest.
If your goal is instead to cut down on hotel costs, the Marriott Bonvoy Business American Express Card can be an excellent choice. This card comes with a free annual night certificate that helps offset the annual fee every year.
As with the Aeroplan strategy, Chexy also speeds up point accumulation that can later be redeemed for free nights across more than 30 Marriott brands, including Marriott Hotels, Sheraton, Westin, Delta Hotels, W Hotels, and St. Regis. For entrepreneurs who travel often, or families looking to cut vacation costs, this strategy can carry real value.
Earning points through your business spending can be an excellent strategy, but it’s important to understand that certain tax considerations may apply. The tax treatment of points varies depending on the nature of the expenses, your business structure, and how you use the rewards.
For example, an entrepreneur who earns points through business spending and then uses them for a personal trip may need to determine whether that benefit carries tax consequences. In the specific case of a corporation, if points are earned through expenses paid by the corporation and then used for a shareholder’s personal trip, the Canada Revenue Agency could, in certain circumstances, treat the value of that benefit as a taxable benefit to the shareholder.
This doesn’t mean you should avoid the strategy. Many entrepreneurs use business credit cards to maximize their spending and take advantage of rewards programs. What matters is keeping proper documentation, clearly separating personal and business expenses, and consulting a tax professional to confirm the rules that apply to your situation.
For more on this topic, see our complete tax guide on points earned through business spending.
Chexy isn’t necessarily the best solution for every expense, nor for every entrepreneur. The goal isn’t to pay fees just to earn points, but rather to strategically use expenses you already need to make.
Before using Chexy, take the time to weigh:
If you’re a self-employed worker or a small business owner who already makes significant payments every year, Chexy Business can become a valuable optimization tool. Paired with a business credit card suited to your goals, this strategy can help you unlock welcome offers more easily, earn Aeroplan points, Marriott Bonvoy points, or Membership Rewards points, and in some cases, get those rewards at a lower cost than buying them directly.
As with any financial optimization strategy, it’s important to weigh the fees, the real value of the rewards you earn, and the tax considerations that apply to your situation to decide whether Chexy makes sense for your business. Also check our best credit cards page or our selection of the best business credit cards to compare all the options available.
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