Save on all Your Flights with THESE Hacks

Dear Rich Lifer,

One of the most common things people want to do after they retire is travel. You’ve got the time, you’re usually free from familial obligations, and it seems like there’s no time like the present to finally see all the places you’ve dreamed of for so long.

The biggest obstacle to making these dreams a reality is almost always the cost. 

Travel can be expensive! And sure, you can fly standby and stay in hostels to save some money, but you should live a little when we get to our destinations, so the thought of scrimping simply doesn’t appeal. 

There are a few major ways you can travel in style and still save big, though. One of the best places to save is actually the airport, and there’s one airline that offers lots of extra perks and ways to save so you can get where you’re going for less. 

Southwest Airlines used to be the little guy with only a handful of destinations, but as of January of 2020, they now fly to over a hundred destinations in 11 different countries. We’re talking everywhere from Portland, Oregon to the Bahamas, and from Hawaii to Washington, D.C. They’ve even got service to certain South American countries, too. 

Southwest is able to maintain a high quality of customer service and lower prices because they do things a little bit differently than other airlines. For example, to save money, they often fly into secondary airports – like Chicago’s Midway instead of O’Hare or Dallas’s Love Field instead of DFW. Then they pass these savings onto the passenger. 

That’s not all they do, though. There are several ways you can save money by flying Southwest. 

Here are eleven of my favorites…

Sign Up For Rapid Rewards

Like many other airlines, Southwest has a loyalty program. You can earn points towards free flights just by flying, and you can also use them by going to partner businesses like certain restaurants, car rental agencies, and stores. Signing up for a Southwest credit card will help you rack points up even faster. 

Bring A Friend

If you fly a lot, you can earn a Companion Pass. When you complete 100 qualifying flights, your companion will be able to fly for free! You can also use Rapid Rewards points for this, so if you make a Southwest credit card your main card, you can get to Companion Pass status faster. 

Get Perks To Keep Or Sell

After you’ve taken 10 one way flights with Southwest, they’ll mail you drink coupons good for free alcoholic beverages when you fly. You can use these yourself, or sell them – they can fetch $15 or more on marketplaces like eBay.

Take Your Stuff With You 

Many budget airlines have cut out baggage allowances, which means their tickets look cheap… until you get to the airport and find out that bringing your bag will cost another $50 each way. Southwest lets you bring two checked bags, a small carry on, and a personal item at no additional charge. 

Change For Free

If you need to change your flight after you’ve booked, no problem. Southwest lets you make the change without paying the hefty change fees that other airlines charge. 

Get An Adjustment

Don’t you hate it when you buy something only to see it on sale a few weeks later? Southwest makes sure you never have that problem – if you see a lower price after you’ve booked, just give them a call and they’ll give you a price adjustment. 

Wait To Upgrade 

If you want to board the plane and choose your seat first and get a free cocktail or other alcoholic beverage, you might be tempted to spring for business class when you book your ticket… Don’t do it, though – those fares are often double the lowest “Wanna Get Away” fare. Instead, wait until the day of your flight and upgrade at the gate. You can get the same perks as if you’d paid ahead of time, and this way, it’ll only be an extra $30 or $40. 

Set Your Alarm To Save

You can sign up to get Southwest’s emails – they’ll let you know what routes are going on sale and when. If you need to go somewhere specific and don’t have time to wait for a sale, just make sure you’re on the Southwest site on Tuesdays at 3pm. That’s when their fares are the lowest they’ll be all week – and remember, if a sale pops up later, you can always ask for an adjustment!

Stay Entertained For Free

Gone are the days of everyone watching the same inflight movie – but only if they paid for the headphones! Southwest gives you free games to play and 18 television channels to watch from your device using in-flight WiFi. (WiFi is $8 if you need to use it for something else.)

Use Coupons

The in-flight magazine has the typical information and articles you’d expect to find, but if you keep flipping through, you can also find coupons for parking and even restaurants in your destination cities. 

Double Dip On Savings

While it already seems like Southwest is a pretty good deal, you can get their tickets for even cheaper using Southwest gift cards. Simply purchase the gift cards at Target with the Red Card to get them for 5% off, or at Sam’s Club – they often have $150 in cards for $143. Then you use the gift cards to pay for your flight – easy, right?


There are lots of airlines to choose from, but, again, Southwest has a great mix of price and value. If you decide to cross shop against other bargain airlines, don’t just look at the initial ticket price. Be sure to account for all the fees you’ll be charged (including the baggage fees) in order to get an accurate comparison. 


If you’re ready to get out there and fulfill your travel dreams, give Southwest a shot – you might be pleasantly surprised!

To a richer life,

Nilus Mattive

Nilus Mattive

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Nilus Mattive

Nilus is the editor for the daily e-letter The Rich Life Roadmap and a Paradigm Press analyst.

Nilus began his professional career at Jono Steinberg’s Individual Investor Group, where he published his original research through a regular investment column. Later, he worked for a private equity business and spent five years editing Standard and Poor’s...

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