How to Book Cheap Flights for Sabbaticals and Other Travels

One of the most common questions for new solo female travelers (or even the more veteran among us!) is how to book cheap flights. Airfare has gone wild since the pandemic and there is so much bad advice out there. The good news is that booking cheap flights can actually be very simple. The bad news is cheap airfare requires something that many travelers aren’t willing to embrace: flexibility! Here I’m using an example how I booked a round-trip flight from the US to Paris for less than $500 (even including all the taxes and add-ons and hidden fees), but this process can also help you save money on sabbaticals anytime you fly. Read on to see see just how powerful a tool your flexibility can be!

6 Steps to Book Cheap Flights

Step 1: Sign Up for Flight Deals Newsletters

There are loads of companies that have devoted their entire business to finding great deals on flights. Many offer free newsletters, but it can also be worth it to pay for a subscription. Either way, when you sign up, you’ll receive tons of emails every day highlighting the best priced airfare routes from airports near you. 

One of the best newsletters, Scott’s Cheap Flights, has recently rebranded to Going. Other good choices include Dollar Flight Club, Matt’s Flights, and Jack’s Flight Club.

(Keeping an eye on these newsletters will also give you a good knowledge base for what’s a good price to different destinations and what kinds of deals pop up more frequently.)

Step 2: Pick Your Destination Based on the Deal

It’s become a popular chorus on social media to “choose the deal, not the destination.” If you want to travel and don’t have a lot of money for it, I cannot stress enough how important this is! 

A coworker once asked me how to book cheap flights and I geared up to rattle off a bunch of advice, only to hear her say she *had* to go to Denver and it *had* to be in three weeks. (She was going to a friend’s wedding.) Unfortunately, in a situation like that, the only thing I could say to her was “Sorry girl, you’re screwed.”

If you are absolutely locked in to a specific destination at a specific time, the only thing you can do is book as early as possible and hope the price doesn’t drop in the future. (Or use Google Flights for its price guarantee feature.)

If, on the other hand, you plan your travel around the best deals you can find, you will always be able to book cheap flights to almost anywhere.

For my trip to Paris, I noticed an email from one of my flight deals newsletters highlighting a $300 round-trip base airfare.

I’ve been to Paris a couple times before. I probably wouldn’t have set out to visit again, but that deal was too good to pass up and I know there’s enough that I haven’t done in the city that I’m still going to have an amazing time.

Step 3: Search Flights on Skyscanner or Google Flights

I have spent hours upon hours testing the same routes across different flight search engines and both Google Flights and Skyscanner surpass any other search aggregates out there.

Both tools make it easy to scan a whole month at once for the best price. Flight deals newsletters are giving you the heads up that there’s a deal out there, but the window for when that deal is available might be huge, like March to August. That’s not super helpful in finding where in that six-month span the lowest price is actually lurking.

So you’re using the newsletter to choose a destination based on a deal being available and then using Skyscanner or Google Flights to hunt down the cheapest dates.

If you’re more flexible on your destination than your dates, both tools technically have an “Anywhere” or “Everywhere” feature that allows you to explore the cheapest routes from your starting airport. This is still much better on Skyscanner than on Google.

Step 4: Check Your Itinerary Before Booking

Once you find the fare you were looking for, don’t rush to book it! You want to pay careful attention to these things:

• How long the flight is
• Whether there are any connections, and how long those connections are
• What time the flight arrives in your destination
• How much the same route costs on a major airline

(This checklist is a must-have for sabbaticals! You’ll have so many more moving pieces to keep organized and glossing over the details is where mistakes can crop up.)

You want to look at flight duration because there might be a limit to what you personally tolerate. If you can’t stand the idea of a 22-hour travel day once your connections and layovers add up, you might rethink this particular trip.

Even if you’re okay with a longer door-to-door travel time, you need to pay attention to your connections. With delays and cancellations more common these days, it’s actually a really good idea to pad your itinerary with a longer layover if you can’t fly direct.

For my flight to Paris, I unfortunately have just a 1-hour layover in Reykjavik which is very tight to begin with. If my first plane gets delayed, I could be in real trouble. (The good news is I’ve flown through Reykjavik before, so I’m familiar with the layout and I know that at this time of day, it’s not too busy.)

As a solo female traveler, I am always keenly aware of what time a flight is going to land in my destination. I do not like venturing into strange cities outside daylight hours. If my flight lands at night, I will either spend the night in the airport or I will book a different flight.

Finally, it’s worth actually checking the cost of a major airline for the same route so you understand how much you’re really saving. Many of these bottom dollar airfares are possible because they are with budget airlines on a super scrimped basic economy class. A major airline is more likely to include some amenities in the base fare that the budget airline will charge you extra for. Make sure you’re actually getting a good deal!

Which brings me to…

Step 5: Start the Booking Process to Check Add-On Costs

My base airfare to Paris was about $300 round-trip, which is mind-boggling. But by the time I was done booking, I was actually paying about $500 round-trip. This is still a very good deal on airfare! But it’s not quite as amazing as $300 round-trip.

Play Airline, a low-cost carrier based in Iceland, charges extra for anything more than a personal item. So I’m paying $114 more for my carry-on backpack.

Because my connection in Reykjavik is so tight, I felt it important to sit in an aisle seat near the front of the plane so I can deboard as quickly as possible. Seat selection cost an extra $55.

And then there are all the extra taxes and fees that all airfares get hit with.

It’s important for you to start booking so you see how those costs actually add up. Don’t rush and don’t be afraid to abandon cart if the deal you’re chasing turns out to be too good to be true.

Step 6: Complete Your Booking

If you’ve checked all the details and this still feels like a good enough flight for a good enough price, go ahead and book it!

Congrats – you just booked a cheap flight and you’ll be able to do it again and again.

Should You Search for Flights in Incognito Mode?

This is a terrible piece of advice floating around online that I myself perpetuated for years before getting set straight by a former airline employee.

Many people believe that cookies attached to your flight search history artificially drive up the costs and you will somehow magically find cheaper airfares simply by switching to a private browser or incognito mode.

I know how tempting it is to believe something that simple could give consumers greater control over flight costs, but it’s just not true.

If searching the same route over and over was what increased the flight cost, then how do you suppose travel agents or the companies running those flight deal newsletters ever find cheap airfare? These folks are doing nothing but searching airfares all day every day and they never have trouble finding great deals.

What’s really happening is this. Even though we the consumers only see a few flight classes (economy, business, first, etc.), on the back end, the airline actually has dozens of booking codes that price every seat on the plane individually.

Your flight search will return the least expensive fare available. If you see a flight priced at $150, it could be that only one seat on the plane is left with that particular booking code. If somebody books that seat while you’re refreshing your search, you’ll be shown the next available seat with a higher price.

If you want to keep searching in incognito mode, that’s fine. It’s not detrimental to your flight costs. It’s just not the magic bullet so many on the internet claim.

How to Book Cheap Business Class Flights

There are three ways to get good deals on business class flights and most of them start with the specific airline you want to fly with.

The first is to sign up for that airline’s email newsletter so you get notified of any major discounts they have available.

The second way to book cheap business class flights is to sign up for that airline’s loyalty program. It’s usually free to sign up and start earning status with them. When you reach an elite status with an airline, you can redeem points for a free upgrade, but any amount of membership or status can work in your favor if you want to try and ask for a free upgrade.

You could also get an airline’s credit card and earn frequent flier miles that way. (This is best covered in another blog post though!)

The final way to book cheap business class flights is to bid for an upgrade. All you do is check a little box indicating you would like to be considered for an upgrade and enter how much you would be willing to pay. If the airline doesn’t sell all the business class seats on that flight, they’ll open it up auction-style to the folks who selected that bid for upgrade option. If you win, your credit card will be charged in the amount you bid and you’ll receive your upgrade confirmation. If you aren’t so lucky, you don’t get charged anything and keep your original booking.

Can I Just Ask the Flight Attendant for a Free Upgrade?

I mean, technically yeah, you can, but they’re flight attendants… not fairy godmothers. Some airlines have hard policies against upgrading anybody to Business or First Class if they didn’t pay and aren’t part of the loyalty program.

But if you really, really want to give this a try, show up early, be nice, and use this script from upgrade queen Gabby of Packs Light with the gate agent. (That’s the gate agent, not the flight attendant!)

A Final Word on Booking Cheap Flights

Booking cheap flights (and even scoring upgrades) is all about your attitude. Staying flexible and grateful for the privilege and opportunity to travel at all makes booking flights so much less of a headache! There are amazing places to experience all over the world. If you stay focused on that, you will always be able to find an affordable flight anywhere worth going.