With March break right around the corner you might be looking to take a trip to “escape” (probably not the best choice of word considering the winter we’ve had here in Toronto) the winter blues. Before you go rushing out to your local travel agent (sorry, but they have the worst prices from my experience and unless you need their knowledge they are a waste of time), here are some cheap travel tips for booking travel online within Canada.

Before I get started I will try to explain why I think I am qualified to write this kind of article. During the last 6-7 years I have spent a lot of my free time traveling around the world. Most years I have ended up taking between 3-5 trips all over the place including the USA, Caribbean (including cruises), Mexico, South America and Europe. Since there is nothing more that I hate in the world than being ripped off, I have spent extensive amounts of time doing research for each of these trips just so that I can get the best prices. I travel at all different times of the year so I am familiar with the high and low seasons and often will book my travel around these things (because my schedule is flexible it allows me to do so).

Here are some of my best tips when it comes to booking travel online:



One of the most important things to consider when it comes to booking a trip is when you are going to go. If you have no choice in this matter then unfortunately this section will not apply to you so you can skip ahead, but if you have some flexibility there are some important things you should know about when to book your trip. When it comes to travelling down south the peak travel times are typically from about the 20th of December until the 1st week in January and mid February until the last week in March. If you have to travel during these times, expect to pay top dollar! If you are a bit more flexible, you can try timing your vacation to just outside these periods as often prices will be as much as 50% less! As for Europe, peak season is usually during the summer break for schools (late June until 1st week of September). Deals can still be found during these times as there is also an increase in charter flights during this time but often you need to wait until about 3 weeks before to get the best deals.



After you have taken the season into consideration the next question is when should you actually book your trip? This obviously depends on your own flexibility but from my experience the best prices are typically found between the 3-5 weeks away from the travel date period. If you have to book well in advance due to your job requiring you to request the time off, try to hold out as long as you can and continue to monitor the prices during this time. Prices with travel ALWAYS are based upon demand, so the higher the demand, the higher the price will be. You used to be able to hold out until the very last minute and pick up a “last minute deal”, but in recent years I have noticed the number of these deals are few and far between. It seems as if the airlines would rather have empty seats on their planes then to sell them off at a very low price.



Montego Bay, Jamaica

Booking your vacation as a package is often one of the best ways to save money on your trip. Since you are bundling everything together with the same supplier, they can take a hit on their commission for one of the components of your trip just to sell you the other. A vacation package can be as simple as combining a flight and hotel but can get even more complex to including hotel, food, drinks, transportation, tours and your flight. Depending on where you want to go, I suggest checking out these different sites for the best prices: NOTE: One thing to note is most travel websites are pulling from the same database. The sites listed below are only my recommendations of the ones where I have found the best prices when I have compared the exact same trip on multiple sites

Europe – Packages to Europe are few and far between, though Portugal, Spain, France, Italy & Greece are the most popular when it comes to packages. For these destinations I have found the best place to start looking at prices is either on Tripcentral.ca (click on their vacation pricing grid and look for the European country of your choice) Expedia.ca. Once you have used these sites, you will be able to determine which tour operators are flying to these destinations (ie. Sunwing, Air Transat, etc.) then compare the price of these sites with the price of booking directly through the agent themselves. For other destinations I would look at Expedia.ca to make a “custom” package as these are much more difficult to find.

Caribbean/Mexico – When it comes cheap Caribbean travel, your best bet is to go with an all-inclusive package where everything (flight, transportation, hotel, food & drinks) is included in the price you pay at the time of booking. The cheapest destinations are typically Cuba or Dominican but if food is important to you I would shy away from these unless you are booking a 5-star. There is a saying that goes, “a 4-star hotel in Cuba is like a 3-star everywhere else”, so keep this in mind if you are booking here. I have been to Cuba though and loved my time there, so don’t let me scare you away as I would definitely return! My favourite Caribbean destination so far has been Jamaica (great food!). Of course, do your own research and decide where you want to go first. To find the lowest prices for these kind of trips, I tend to stick with either Trip Central (I love their grid) or Selloff Vacations (sometimes a few dollars cheaper than Trip Central) for booking.

USA – The most common destinations for Vacation packages within the United States are Florida and Las Vegas. For Florida packages I would look at either Trip Central or Expedia. As for Vegas I usually stick with Vegas.com or Expedia. One thing to consider when traveling to the United States is if you live close to the border, sometimes you can save some money by crossing the border and flying out of the closest US airport. Also with all US vacation packages I would suggest doing a price lookup on an American website such as Orbitz.com to see if their pricing is similar.

Cruises – I have only been on 3 cruises in my life so I don’t have as much experience booking these types of vacations as I do some of the others. From the limited research I have done though I have found that Cruise.com had the best prices in most of the cases when I was looking. They are an American site, so prices are listed in US dollars, but with conversion rates nowadays it’s basically on-par with our dollar. You can also try any of the sites listed above as most of them will have a tab for cruises.



Before you book any hotel anywhere, I would suggest doing some research on the place first. My favourite site for looking up hotel reviews is by far TripAdvisor.com. They also have a tool to help you do pricing research (it compares prices on around 5 different travel sites) which is quite good for helping narrow your search down. Similar to Vacation Packages, booking a hotel is also very location specific:

USA/Canada – If price is your #1 priority, my favourite sites are Priceline.com and Hotwire.com. Both of these sites allow you to suggest your own room price and if you are lucky a hotel will accept it. Bidding on travel is a much more in-depth topic that would require its own blog post and if you would like me to write one just leave a comment below. In the meantime, I suggest checking out BetterBidding.com for tips on how to use these sites. If bidding for travel is not your thing, the next thing you can do is check out some of your favourite Group Buying sites, such as Groupon. Many of these sites have no added a travel or “getaways” component and list many different hotel options. Travelzoo is also another site I often will check before booking travel anywhere. Every week they put out their “top 20 travel deals” which typically contain a few hotel deals, some flight deals and some packages. Their deals used to be much better though in recent times I have noticed they aren’t nearly as good. Of course if all else fails with any of these sites you can always check the big sites such as Expedia (Canadian site) and Orbitz (US site).

Europe – I am still trying to find a really good site for booking hotels in Europe so if anyone has any suggestions please leave a comment below. I have found that some sites specialize much more in certain countries then others. For the most part I typically use Booking.com (lots of great last minute deals) and Expedia.ca when looking for hotel deals in Europe.



Depending where you are travelling to in the world, there are often several alternatives to a hotel. The most popular choices are hostels, bed and breakfasts (B&B for short) and short term rentals. Quite often you will get an equal level of quality (possibly even better) at these types of accomodations than you would staying at a hotel. Here are some sites to check out for each of these types of accomodations:

Hostels – The thing I love most about hostels is they are a great way to meet other travellers. Prices can range from very inexpensive if you are willing to share a room with several people, or can increase if you want your own private room (which can be equivalent in quality to many hotels). Depending where you are in the world, many hostels provide some of the nicest accommodation in the area. I have only ever used HostelWorld for booking stays at hostels but Hostelling International is a great organization that allows you to book hostels that meet their standards.

B&Bs – A bed and breakfast is another great alternative to a hotel as you will get a much more personal level of service and they are typically much quieter than hotels. I am not familiar with sites to research these but when I searched on Google, the first two results were BBCanada & BedAndBreakfast.com.

Short Term Rentals – Short term rentals are typically someone’s residence that they have turned into a rental property for vacation rentals. This is a great option for accomodation because unlike most cramped hotel rooms, you will get a full living space including kitchen and other ammenities. I have personally never used one of these, but I was recommended to check out AirBNB and VRBO. If anyone has any more vacation rental recommendations please let me know in the comments!



Finding a cheap flight has been made much easier with technology and now the Internet. There are many sites that can calculate the lowest fares to many destinations where there isn’t an option for a direct flight, but when there is a direct flight you can sort them by fare also! One of the sites that does this best is Kayak.com. Their search tool makes it very easy to find the best rates for your destination and then takes you to the page on the supplier’s site where you can book the deal. They only make their money from advertisements and any affiliate deals they have in place from what I can tell. I know this is starting to sound like a broken record, but I also will compare them with CheapTicketsCanada and Expedia (trust me I am not being paid by them for this article, they just are one of the biggest sites and have one of the most user friendly interfaces which is why I recommend them).

One tip to consider when trying to find a cheap flight is whether there is a tour operator flying there. If they can’t fill all the spaces on their tours, they will usually sell the flights off at a very low price. The downside of this is when something goes wrong with a charter’s plane you can expect very long delays! I spent 36 hours in Rome last summer waiting for my plane to be fixed. The largest tour operators that I am most familiar with are Transat Holidays, Sunwing Vacations, and Sunquest.

Another thing to consider is when it comes to flying is where you are departing from. For example in Europe there are RyanAir and EasyJet which specialize on cheap flights from the UK and within Europe. Be sure to look for any locally specific airlines that are more specific to your travel plans.

One last thing I would like to touch on is “seat sales”. Many airlines run promotions claiming 50% off their regular prices but in reality many of the times I don’t think you are even getting a deal at all. It seems like they simply raise their regular price just to pretend it is being discounted. This brings me to an important point with travel, it is important to educate yourself on the pricing for destinations where you are interested in going. Knowing what the pricing typically is throughout the year for a destination will make it easier to determine if you are getting a great price, or are just getting ripped off. Pricing is dependent on many factors such as fuel prices, inflation and demand so remember this when doing your pricing research.

UPDATE (December 14, 2012) – I just discovered a site that has great deals for people living in Toronto. The site is called YYZDeals.com. They look at all sites and post the best deals (mainly for flights).



Two of the most important things to consider when travelling is what you are going to do when you get there and how you are going to get around to do them. Sometimes you will need to rent a car, but often walking, public transportation or taxis are the best ways to get around. I never book tours in advance as I find a lot of the time you are paying a premium for this organization and I don’t like to be kept to a schedule when travelling, but if you do like this structure then many travel providers will let you book excursions, tours and transportation when booking your trip. I would suggest you always do some research on sites like TripAdvisor before going away so that you can be prepared for when you arrive at your destination. Depending on where you are going, be smart when travelling, stay alert (as not all Countries are as safe as Canada) and have a great trip!



I hope you found this article useful and if you have any other tips on things I missed or didn’t cover, please leave a comment below. If you enjoyed reading this article I would really appreciate if you either leave a comment below or clicking one of the share buttons below for your favourite social network. Thanks in advance!