Chexy’s First Class Contest Offers Business Class Trips for Two

Chexy’s new “First Class” contest is giving away three business class trips for two, each valued at approximately $30,000 (CAD), across three draws this fall.

Every grand prize comes with round-trip business class flights, five nights of luxury accommodation, curated experiences, and $1,000 (CAD) in spending money. The first winner is headed to the French Riviera for five nights at the Hôtel Martinez in Cannes.

This one lands close to home for us, as Prince Collection, Prince of Travel’s in-house luxury travel agency, is the official Travel Partner designing and delivering the trips. Draws take place on September 1, October 1, and November 1, 2026, with 999 Chexy Cash prizes joining the grand prize for 1,000 winners each time, and first-draw entries close August 31, 2026.

How the First Class Contest Works

The contest runs from July 24 to October 31, 2026, with three draws along the way. Entries you collect count toward the next draw on the calendar, then reset for the following period.

Destinations, dates, and itineraries are indicative until the sponsor and Prince Collection confirm them at booking, and entries for each draw must be in by 11:59pm ET on the final day of the period.

Every draw crowns 1,000 winners. One takes home the grand prize trip, while the other 999 receive Chexy Cash prizes ranging from $5 to $2,000 (CAD).

Chexy Cash is promotional credit redeemable against payments in the Chexy app, and it expires 12 months after it’s issued.

Anyone who is a Canadian legal resident, Quebec included, and has reached the age of majority in their province or territory can enter. Winners need to answer a skill-testing question, odds depend on the total entries received, and the fine print lives in the official contest rules.

How to Earn Entries

Entries are capped at 100,000 per person per draw period across all methods combined, and there are plenty of ways to stack them up:

Note that registration happens in the Chexy app, where you accept the contest rules with a tap of the “I’m in” button.

Otherwise, the free email route asks for a 100-word original response and awards 100 entries on your first submission each draw period, with one entry for each additional response. You don’t need a Chexy account to enter this way, though you’ll need one to claim a prize.

Turning Your Regular Bills into Entries

For anyone new to the platform, Chexy lets Canadians pay rent, utilities, insurance, tuition, daycare, condo fees, and even income taxes with a credit card, in exchange for a processing fee of 1.75% on Canadian-issued cards, the lowest among Canadian bill payment platforms. American Express, Visa, and Mastercard are all accepted, and payments you could never put on a card otherwise start earning rewards.

Mortgage payments joined the lineup earlier this month through the platform’s new Aeroplan partnership, earning 1 Aeroplan point per $1 from a bank account. Chexy has confirmed those payments earn contest entries as well, which turns the single biggest bill most households carry into a serious entry engine. You’ll find a full breakdown of the platform in our complete guide to Chexy.

Since every dollar routed through Chexy earns an entry during the contest, the math scales with the size of your bills. A $2,000 monthly rent payment adds 2,000 entries per draw period, a $3,000 mortgage payment adds 3,000 more, and a larger one-off payment, like a quarterly tax instalment, can add five figures in one shot.

The regular rewards don’t pause for the contest, either. Your credit card keeps earning its usual points on every payment, with premium Aeroplan co-branded cards earning up to 1.25 points per dollar through the platform. Holders of eligible American Express cards, including the Platinum Card and the Aeroplan co-branded cards, can also collect 250 bonus Aeroplan points on single payments of $1,000 or more, up to 500 points per month, under a separate offer running through October 31, 2026.

Referrals do double duty during the contest, too, and they work whether you’re a new or existing user. Each friend who’s new to Chexy and makes their first bill payment through your link hands you 10,000 contest entries, alongside 1,000 Aeroplan points per referral (capped at 10 per calendar year). Chexy’s referrer tiers will also cut your processing fee to as low as 0.5% once you’ve brought in 10 people.

The Grand Prize Trip

This is where I’ll toot our own horn a little. Prince Collection is named in the official rules as the contest’s Travel Partner, which means our team designs each winner’s trip, from the hotel to the transfers to the curated experiences that round out the five nights.

Every stay is booked through Prince Collection’s preferred-partner programs, so winners check in as VIPs, with room upgrades where available, daily breakfast, a property credit, late checkout, and recognition on arrival. The team coordinates the stay, transfers, and experiences directly with each property, shaping them around the winner’s preferences.

Travel is scheduled to take place between early September and early December 2026. Winners won’t be choosing their own travel dates or destinations, as those details are determined by the contest.

Chexy’s campaign page fills in what the first trip looks like, and it’s a proper Riviera itinerary, with business class flights both ways, five nights at the Hôtel Martinez in Cannes, and a private yacht outing on the Mediterranean.

Prince Collection has since shared what it’s coordinating with the hotel for the winner’s stay, and the lineup reads like a Riviera greatest hits:

• Luxury round-trip transfers between the airport and the hotel
• A half-day private yacht charter to the Lérins Islands, cruising the Bay of Cannes with swims in the crystal-clear coves around Sainte-Marguerite Island
• A private driver day along the coast, taking in the medieval village of Èze, the Fragonard Perfumery, and Monaco’s Casino Square and Prince’s Palace
• A curated dining experience at one of the region’s most iconic restaurants, with La Palme d’Or in Cannes and Louroc at the Hôtel du Cap-Eden-Roc among the contenders

Winners will want a passport valid at least six months beyond the travel dates, plus emergency medical insurance for the destination, both of which the rules require.

Conclusion

For anyone already using Chexy to pay rent or recurring bills, the First Class contest requires very little extra effort. You can accept the contest invitation, continue making the payments you would normally make, and accumulate entries ahead of the first draw on September 1.

Even if you aren’t currently a Chexy user, there’s still a free email-entry option that gives you 100 entries without requiring a payment. And with the recent addition of Aeroplan rewards on mortgage payments, the broader Chexy platform may be worth exploring regardless of the contest.

We’ll be paying particularly close attention when the first winner is announced. Hopefully someone reading Prince of Travel could find themselves travelling business class to the French Riviera this fall on an itinerary put together by Prince Collection!