The Best Websites and Apps for Booking Travel
Updated: Apr 22, 2021
A popular question I receive on Instagram or LinkedIn is something to the effect of “Which website or platform do you use to book your travel?” Here you’ll find those answers. I’ll update this as my habits change.
PS: One other question I receive (and the answer varies) is ”Do you book your airfare or hotels first?” I will always book airfare first because the rate has a higher probability of changing than a hotel. However, I never book my flights until I fully research where I am staying and what my options are. One of the biggest mistakes you can make is staying in the wrong part of town.
Before you continue reading, see my post titled 5 Things to Consider Before Booking Travel.
Frequent Flyer Miles
As a rule of thumb, when I come up with a destination, I check my frequent flyer programs to see where my miles can take me.
Credit Card Rewards
I usually redeem points from my Capital One Venture to book airfare.
Scott’s Cheap Flights
I subscribe and their mailers have actually inspired some spontaneous bookings. Click below to get a free month of their premium mailer, on me!
The best way to gather travel inspiration. Use their flight tool to discover the best deals for the upcoming weekend or month.
Do your research with Skyscanner and book with CheapOair to earn great rewards. CheapOair even lets you pay in installments with little to zero fees. Also use CheapOair for car rentals!
When I actually book my flights, I don't usually book direct through the airline. You should maximize your miles and rewards by earning with a travel agency like Booking.com and attaching your frequent flyer program to your account.
American Express offers 5x rewards when you book through www.amextravel.com with your American Express Card. They also sometimes have better rates than the airlines do and you can apply your frequent flier number to gain loyalty. I usually compare google flights with AMEX Travel.
Lodging & Accommodations
Hotel Loyalty Programs
If I know I’m going to be staying with a major hotel chain, I’ll first check to see what I can get with the loyalty programs which I’ve signed up for. Free is always best, but make sure you aren’t using more points than you have to. Do the math.
TripAdvisor has been incredible when planning my trips. The reviews, traveler photos, and ability to sort by ranking is great. I don’t book through TripAdvisor, I only use them for reviews. IMPORTANT: Always try to book directly with the hotel website so you get points and stay credit. I’ve found you get treated differently if you book through a third party site. PS: click the image below to be directed to one of my favorite stays at a hotel that I couldn't have found without TripAdvisor!
Credit Card Rewards
I don’t usually book hotels with credit card points, but it’s always good to consider.
If I’m struggling to find suitable accommodations on TripAdvisor, I’ll use Google next. Google is great for finding other blogs which review the best or most unique lodging experiences in a certain area. I have actually booked trips because I stumbled across a website showcasing an incredible hotel, which then inspired me to look into that country and research my trip.
Normally while I'm chain booking hotels, I'll book direct through the hotel website to get maximum benefits, but for boutique hotels, it's perfectly fine to use a travel agency. Use Booking.com and earn rewards as well.
I love this app. The rewards are good, rates are great. This is the third party site I use most because of their discounts. I also use this for road trips when making arrangements at the last minute.
Airbnb & VRBO
This is usually a last resort for me and I’ll explain why. Airbnb is an excellent choice for people who want to stay in a great location for a serious discount. It’s also perfect for family or larger group trips of 5+.
It is a last resort for me because the check-in times can be very strict. More often than not, I’m checking in sometime in the evening. Some Airbnb hosts have to hand deliver your key to you and they aren’t willing to wait 4 hours for you to show up. I prefer flexibility to check-in whenever I’d like. If I know for a fact that I’ll be able to check-in at a certain time, then I’m happy to book with Airbnb.
You can expect to find excellent rates here, but it's not my first choice.
Frequent Flyer/Hotel Loyalty Programs
Book your rental with loyalty miles/points and save some $$. Ensure it makes sense though!
Geared toward private aviation, but they will drop off at commercial airports and their cars are loaded and immaculate. They don’t have locations in many cities, but give it a shot. Tell them Jordan sent you!