Traveling Opportunistically – Forbes Advisor
When my friends and colleagues see me and my travel friends jetting off to Asia for an extended weekend, or enjoying a first-class flight to Europe, they often wonder how we do it.
Is it because of our extensive knowledge of miles and points? Do we spend days on end looking for great airfare deals? Do we simply blow all of our discretionary cash on travel? There are probably elements of truth to all of the above. But for the majority of our travels, here is our secret:
We travel opportunistically.
Here’s another secret: You can do this, too!
How Most People Travel
Most people plan travel based on a desire to go to a certain destination at a certain time: A trip to Florida for spring break; a visit to relatives during Thanksgiving; a two-week summer trip to Italy. If there is some flexibility, it might involve flying out a day earlier or returning a day later, or maybe shifting the entire trip by a week or two.
Planning travel this way often means paying the going rate for air transportation. Unfortunately for the traveler, airlines have entire departments dedicated to revenue management, focused on making flights as profitable as possible, which means charging higher prices to high-demand locations when people want to travel most and have minimal flexibility. There’s a reason why flights to vacation destinations during spring break and cities hosting large events are often sky-high; the airlines want to maximize the money they make on every flight.
Traveling Opportunistically Defined
In contrast, I and many of my friends in the travel hacking community often travel opportunistically; we are fairly open on dates and destinations and let the airfares dictate where to go. If we find a $500 airfare to St. Petersburg, we’ll spend a week exploring parks, palaces and churches and enjoying world-class opera and ballet. If a $50 airfare to Washington, D.C. pops up, we’ll jet out for a weekend, see some friends and visit a Smithsonian museum. We don’t plan travel and then search for airfare; we find good airfares and then plan our travel.
Following airfare sales not only enables us to stretch our travel dollars, but also provides opportunities for off-the-beaten-path experiences. Many of the best airfares are to destinations not frequented by tourists or during off-season times. Everyone wants to go to Munich during Oktoberfest, but what about during December, when the snow starts? A trip off-season to Munich can bring an opportunity to visit Christmas markets, or to experience the city like a local when it is not overrun with tourists… and, of course, indoor attractions such as museums are less-crowded in the off-season.
Reasons to Focus on Finding Cheap Flights
Certainly airfare is not the only, or even the most expensive, cost of travel, but it is often the part that is least-replaceable. If you are traveling to a destination, you likely have many options for lodging (everything from staying at a friend’s place to an Airbnb to cashing points at any number of hotel chains), transit (public transit, rideshares, renting a car getting shuttled by friends) and things to do (museums, coffee shops or game nights with friends) but travel over a long distance in a short amount of time almost always involves a plane.
Types of Flight Deals You Can Expect
If you are looking to travel opportunistically, what might be reasonable expectations for the types of deals you might find? No, you are not going to subscribe to a deal website and magically find $30 airfares to Florida for spring break. Yes, sometimes the best deals mean you’re flying in coach on Frontier or Spirit. And, yes, sometimes you will see phenomenal deals that you simply cannot take advantage of. FOMO looks large when you travel opportunistically.
Here are a few examples of the types of deals I have personally taken advantage of while traveling opportunistically:
- $50 round-trip flights from Minneapolis (MSP to Denver (DEN)
- A $300 round-trip flight from Vancouver (YVR) to Tokyo (NRT) in business class
- A $200 flight from Newark (EWR) to Manila, Philippines (MNL), with a stopover in Honolulu, Hawaii (HNL)
- Multiple sub-$500 flights to Asia
- Multiple sub-$400 flights to Europe (generally in the winter)
- Business class flights to Europe for 27,500 KLM Flying Blue miles
Where to Look for Cheap Flights
There are thousands of places offering “travel deals” online and they range from sites simply parroting advertised airfare sales from airlines, to curated travel deals, to proprietary AI engines that scour the web for any airfares that are out of the ordinary.
Realistically, you probably have some constraints in terms of your flexibility, comfort with international travel or desire to travel to certain locations. Your constraints and travel preferences will determine which travel sites, mailing lists and opportunistic travel options will be most useful to you. The options below are by no means exhaustive, but should provide a good starting point to finding fare deals that you can use.
Google Flights Explore Destinations
Google Flights has become one of my favorite tools for opportunistically booking travel within the U.S. and is the one of the best tools for people who want to travel domestically or have limited windows of time flexibility. The Explore Destinations feature of Google flights lets you view cheap airfares across the U.S. for a wide range of timeframes (e.g. a weekend trip within the next six months or a trip to any destination on a set date). The tool also works for international airfares, but its coverage outside of North America is spotty.
To use Google Flights, head to flights.google.com and click on “Explore” on the left hand side of the page or the “Explore Flights” link above the map, about half-way down the page. From the Explore Destinations map, you can select your desired trip length and timeframe. To find cheaper airfare deals, move the “Price” slider downward left to hide more expensive airfares. Airfares can be explored using the displayed map.
As of writing this, with Minneapolis (MSP) as a base, I am seeing $33 round-trip to Denver (DEN) and $109 round-trip to Portland (PDX). Of course, most of the lowest prices on the site are limited-service airlines such as Frontier and Spirit, I am also seeing direct flights to Seattle (SEA) on Delta across a wide range of dates for under $150.
Airfare Deal Sites
If you are interested in international travel, you will probably find the most success with websites and mailing lists that offer curated airfare deals, with a focus on specific cities or destinations.
The Flight Deal and Fare Deal Alert are two of my favorite sites that fall into this category. Each site covers deals originating from a collection of cities in North America. If you are based in one of the cities that they cover and subscribe to their alerts, you are almost certain to find a deal on airfare that is interesting to you.
By subscribing to their Twitter feeds (@TheFlightDeal and @FareDealAlert) you can get notifications pushed to your phone when they post about an airfare sale so you can book it while it is still available. And if you’re not on Twitter, get on it. It’s the best way to find deals, bar none.
The Flight Deal and Fare Deal Alert are by no means the only deal sites out there. Here are some travel deal sites that I and the editors at Forbes Advisor like:
In addition to the sites offering airfare deals for free, there are a number of premium subscription services which provide members alerts to sale and mistake airfares that you won’t find publicly posted elsewhere. Two of these services are Scott’s Cheap Flights and Thrifty Traveler Premium, which both offer custom flight alerts from your selected departure airports.
Finding Award Travel Deals
If you are a collector of miles and points, you have yet another option available for finding great airfare deals. In fact, sometimes the best opportunistic flight deals are on award travel, either through promotions, sales or mistake fares.
Some airlines have periodic award sales that can provide great opportunities to use miles for travel. Delta is known for having unannounced award “flash sales” which offer heavily-discounted award tickets. American Airlines has web-special awards that offer lower prices, but reduced flexibility. United maintains a page of featured awards, which offers flights as low as 5,000 miles one-way.
Some international airlines also offer discounts on award tickets that you can take advantage of opportunistically. One of my personal favorites is KLM/Air France’s Flying Blue Promo Rewards, which frequently offers heavily-discounted and widely available business and coach flights between the U.S. and destinations where KLM and Air France fly.
Many award travel sales can be found by searching airline websites or by following miles and points blogs such as Frequent Miler, View from the Wing or One Mile at a Time. Earlier this year, thanks to a post on Frequent Miler, my mother and I were able to jump on a sale and score round-trip airfare to Lima, Peru for 9,000 Delta Skymiles round-trip. In addition, there is a niche of paid services that will alert you to airfares that can be booked with miles and points.
Don’t Hesitate. Book Now, Ask Questions Later
Often, the very best deals sell out quickly or the published airfares are pulled because they were published by mistake. If you hesitate booking a great airfare, it might not be available in a few hours after you have checked with your traveling companion, sought out hotels or called the friend you can visit in that city.
Fortunately, the U.S. Department of Transporation’s regulations entitle you to a full refund on non-refundable tickets within 24 hours of booking, provided that your flight is at least 7 days in the future and you are booking a flight directly with an airline.
Many online travel agencies also allow you to cancel your trip for any reason within 24 hours of booking and several airlines have more generous “risk-free cancellation” policies. That said, be sure you are aware of where you are booking as sometimes you will see lower fares on a foreign booking engine. There’s not necessarily anything wrong with booking with a less well-known company, but you will have more protections if you stick to one of the major OTAs such as Priceline or Expedia.
Risk free cancelation means that generally, if you find a great airfare that you might want to take advantage of, it’s best to book it now, and ask questions later. Remember, cancellation policies and regulations change. Always check the airline’s or online travel agency’s cancelation policy before finalizing your booking.
Once you have booked your airline ticket, use the 24-hour cancelation period to start looking around for hotel accommodations, car rentals and other pieces of your trip. If you find that there are no hotels available or that the people you were intending to visit are unavailable, most times, you can cancel your ticket and get all of your money back if you cancel within 24 hours of booking.
Booking Airfare Opportunistically is Less Risky Now
Since 2020, several airlines have made many of their tickets changeable, lowering the risk of jumping on a cheap flight deal. Even outside of a risk-free cancelation window, many tickets can be converted to a voucher or travel funds, good for later travel on that airline.
As an example, since I am based in Minneapolis, I often book flights with Delta. Even if I don’t end up taking a trip, since Delta has eliminated its change fees, any airfare that I don’t use gets turned into a travel voucher, which I can use on a trip within one year of when I booked the original ticket. This even includes tickets I book in Basic Economy, through July 31, 2021. Several airlines have instituted similar policies.
A Quick Caution on Mistake Fares
Sometimes a great airfare deal is just a really, really good sale fare, but sometimes airlines regret setting prices too low and sometimes airfares are genuinely published because of a mistake such as leaving off a digit or failing to add proper taxes. When airlines deem that they have sold a “mistake fare” they will sometimes cancel flights that are booked using that published airfare.
If you book an airfare deal that you suspect is a little bit too good to be true, hold off on making non-cancelable travel plans such as non-refundable hotel reservations or tour bookings. Usually, if an airline is going to cancel your ticket because you took advantage of a “mistake fare,” they will do so within a few days of you making the initial reservation.
Waiting to firm up other travel arrangements will provide some protection against losing money on non-cancelable travel arrangements. Also, though many credit cards offer some sort of trip interruption/cancelation insurance, most credit card travel protection programs do not cover cancelations initiated by the airline.
Letting airfares guide us and traveling opportunistically has opened up a world of travel possibilities for me and my friends. We’ve traveled the world cheaply and visited countries that we probably would not have planned naturally.
The “travel hackers” of the world are not the only ones who can take advantage of great airfares. By periodically checking deal sites, strategically following Twitter accounts or subscribing to a flight deal mailing lists, anyone can take advantage of similar airfares and travel opportunistically. If you are able and willing to be a bit flexible and patiently watch for cheap airfares, you too can take to the skies on the cheap.