The Best Travel Websites

I’ve just returned from a cross-country trip and my wife is about to head out on one of her own. I thus thought that now might be an opportune time to talk a bit about travel planning.

Not surprisingly, we do virtually all of our travel planning online. What follows is a rundown of our favorite travel sites, and a few words about how we use them and we like them.


My first stop when planning a vacation is often Kayak. I’ve lumped it together here with Sidestep because they’ve historically offered very similar services, but Kayak ultimately bought Sidestep.

Kayak has by far the best interface of any travel site that I’ve used in recent years, and they also have a very hand iPhone app. You can easily search prices at all major airlines (except Southwest) using Kayak, and they’re live-updating results make it easy to quickly find the best deals.

To be honest, I usually end up booking through the airline website itself (habit, I guess), but Kayak allows me to quickly identify which airline(s) I should be searching.

Bing Travel

This is a relatively new entry on the list, but I’ve recently started checking Bing Travel before booking flights. Why? Because they have a great fare forecasting tool that tells you whether you should buy now or wait.

While no tool can make perfect predictions, my experience has been that Bing does a good job of tracking price trends and letting you know if now is a good time to buy. They also include a confidence rating to give you an idea of how much weight you should give their prediction.

As a quick example, we’re considering a trip to visit family for the holidays, but the prices are a bit too high for our tastes. As for Bing’s view, they’re saying that we should wait, as they’re 84% confident that fares will drop or hold steady over the next week.


I’m tall, so choosing the right seat on an airplane can mean the difference between a reasonably enjoyable trip and hours of discomfort. Enter SeatGuru. They have seating charts for all major plane types on all major carriers, along with comments about the comfort level and amenities associated with each seat type.

If you’re concerned about comfort, I highly recommend checking with them before choosing the seats for your next flight.


If you’re traveling to a new area and want to get the lay of the land, you need to bookmark TripAdvisor. TripAdvisor is an online travel guide that is filled with tons of great user-generated reviews.

While they offer a number of services, TripAdvisor is particularly useful for identifying the best hotel for your needs as well as for finding good restaurants. Like Kayak, TripAdvisor has a handy iPhone app so you can easily check everything on the go (if you have an iPhone).

Hotwire & Priceline

I’ve lumped these two together because I usually use them in tandem. For those that are unaware, both Hotwire and Priceline fall into the category of “opaque” discount travel sites. If you’re willing to forego knowledge of certain details, you can get a great deal by using them.

In short, you retain control of the dates, times, and locations of your travel itinerary, you don’t find out the name of the hotel, airline, or car rental agency until after you accept a price and make the purchase. Purchases are pre-paid and non-refundable, but you can save 30-60%.

The key difference between the two sites is that Hotwire operates on a fixed price model, whereas Priceline allows you to “name your own price.” Of course, there’s no guarantee that they’ll accept it, but it’s worth a shot.

I’ve mostly used these sites for car rentals, though you can get great deals on airfares and hotels, as well. For cars, I start by checking Hotwire. I then take that price, subtract 15-20% and then submit a bid over on Priceline. If they accept, great. If not, I either wait 24 hours and re-bid, or I go back to Hotwire and purchase the rental.

If you’re looking for a vacation rental, I’ve yet to find a better resource than VRBO stands for Vacation Rentals By Owner, and it’s a great resource for finding independently owned vacation homes and condos.

If anything, VRBO can be a bit overwhelming because of the sheer number of options out there. Nonetheless, you can find some great deals if you’re willing to put in a bit of time. This past summer, we used it to book a vacation in St. Augustine Beach, Florida and we couldn’t have been happier with the place we found.

What are your favorites?

Now that I’ve shared my favorite travel sites, I’m interested in hearing about yours. Which sites do you rely on for making travel plans, and why do you like them?

5 Responses to “The Best Travel Websites”

  1. Anonymous

    Tripadvisor is a good review site, especially for hotels, but I like IgoUgo for its members photos and personal travel stories. I usually start reading a review or two and then realize I’ve been on the site for an hour!

  2. Anonymous

    Excellent summary. Kayak is the one I like, but even going to the actual’s airlines’ site can provide you a few savings. Hotwire is very risky, because you can save some money but also end up with a real dud deal. There is a reason why some flights/hotels cannot sell their excess! I say it is worth paying a bit extra for certainty.

  3. Anonymous

    I frequently check individual airline sites for baggage allowances and new rules since those can rachet the cost of your trip up in the bat of an eyelash. To compare baggage costs of major airlines all in one place try searching for ‘airline baggage allowance’ on In my experience, they do a great job of keeping their baggage info up to date.

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