
Top cities for a family holiday
Planning a family holiday from Canada starts with finding the right flights at the right price. Whether you're heading to a sun-soaked beach resort, a theme park adventure, or visiting family across the country, Kiwi.com makes it easy to compare fares for the whole family. Search flights from all major Canadian airports and find deals that work for your family's budget and schedule.
Finding affordable family flights requires planning and flexibility. Start by searching early — 2 to 3 months before your travel date is ideal. Use Kiwi.com to compare fares across multiple airlines and departure airports. For families in southern Ontario, checking Hamilton and Buffalo alongside Toronto Pearson can reveal significant savings. Book mid-week flights (Tuesday or Wednesday) for the best prices. Consider splitting the booking if children qualify for discounted fares on certain airlines, and always factor in baggage costs when comparing prices.
The best time to book depends on when you're travelling. For March Break, book by December or January. For summer travel, start searching in March or April. For Christmas holidays, book by October. Canadian school schedules drive peak demand, so booking before other families snatch up the best fares is crucial. Shoulder seasons — late May, September, and early October — offer the best value, as children are still in school and fares are significantly lower.
Cancun and the Riviera Maya offer all-inclusive family resorts with kids' programmes and water activities. Cuba's Varadero provides excellent value with safe, family-friendly beaches. Punta Cana in the Dominican Republic is known for its stunning coastline and resort entertainment. Orlando gives families access to Walt Disney World, Universal Studios, and countless attractions. Myrtle Beach offers affordable seaside fun. For domestic travel, Victoria, Kelowna, and the Maritimes are wonderful summer family destinations. Montreal and Quebec City offer exciting city breaks with plenty for children to enjoy.
The cheapest times for family travel are the shoulder seasons: late May (before summer holiday pricing kicks in), September (after Labour Day), and October (around Thanksgiving). If you must travel during peak periods, mid-week flights are consistently cheaper than weekend departures. Early morning and late evening flights also tend to be less expensive and can work well for families — children often sleep during red-eye flights.
Travelers booking flights with Kiwi.com often highlight the platform's easy booking process, cheap fares, and clear pricing.
Most travelers appreciate the no-hassle experience and flexibility when managing itineraries or finding alternative connections.
Real customer reviews from travelers who booked with us:
“I had a problem with my return flight as I had a stopover and my first flight was late and made me miss my second flight. kiwi quickly and easily rebooked me on the next flight. the process was transparent and guided by customer service over the phone instead of a machine or chat, which is greatly appreciated in such a delicate situation. I don't usually leave comments or ratings but on this occasion they have earned a positive comment.”
Guillermo D.
“I had heard not great things about kiwi so was really nervous about booking with them. however service was great and flights went smoothly (they even checked in for me!), so it was all in all a terrific experience. I especially liked how quickly they responded to my many queries and how patient they were with me. excellent customer service!”
Marvin Feung W.
“Ability to see prices by day! filters: departure by time, exclude country or airline, etc.!”
Anatolii O.
Updated: May 2026 · Selected reviews from verified customers who rated us 4–5 out of 5. Overall score: 4.5/5 based on 1905 post-booking reviews.
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