While paying taxes to Uncle Sam is never fun for anyone, if you can earn free travel by paying your taxes, it makes the pain of parting with that money a little easier :).

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5 Ways to Earn Free Travel by Paying Your Taxes


5 Ways to Earn Free Travel by Paying Your Taxes via @GotoTravelGal - Make paying taxes a little less painful by scoring some free travel at the same time.


1) TurboTax – 1,000 Points

Free travel by paying taxes - Turbotax

File your tax return through TurboTax online after clicking through the offer from the Southwest Rapid Rewards Shopping Portal and earn 1,000 Southwest points.

You must purchase the 2020 online version of:

  • TurboTax Federal Free Edition
  • TurboTax Deluxe
  • TurboTax Premier
  • TurboTax Self-Employed
  • TurboTax Live

Currently prices range from $40-$90 for these products; you may want to compare pricing to make sure that deal is worth it to you for the points.

Other editions, like the TurboTax CD, are NOT included in this offer.

These are BONUS points, so they DO NOT qualify toward earning the Southwest Companion Pass, which lets one person fly nearly free with you for up to two years.

If you are a member of American Airlines’ AAdvantage frequent flyer program, you can earn 450 miles by purchasing TurboTax through the AAdvantage eShopping Mall.

But American is not nearly as easy to earn free flights as is Southwest!

The BEST way to maximize free flights on American is through the Reduced Mileage Awards program.


2) H&R Block

H&R block

At the Southwest Rapid Rewards Shopping Portal (here’s how to use the Rapid Rewards Shopping Portal if you’re not familiar), you can earn 7 points per dollar on H&R Block tax products.

The program terms state that only TaxCut Premium Software products and TaxCut online products are eligible.

Additionally, there is a 20% discount on online tax filing products through April 15, 2021.

AAdvantage e-Shopping Mall is offering 10 miles per dollar on certain H&R products with a similar discount of 20% off online products.


3) E-File.com

E-File taxes

File your taxes through e-File.com via the Southwest Rapid Rewards Shopping Portal and earn 15 points per dollar.

E-file.com has online tax software for federal and state tax returns.

Prices are up to 50% less than other software programs.

The offer is good for new customers only and for paid products.

AAdvantage e-Shopping Mall is also offering 20 miles per dollar on e-File.com.


4) Pay for These Products with a Miles-Earning Credit Card

credit cards vertical


To maximize the number of points you can earn by completing and paying your taxes through the above, pay for these products with a miles-earning credit card.

We recommend these two cards as top options:

Then, in addition to the points you’ll earn by shopping through your chosen portal, you will earn even MORE points per dollar by using your travel credit card.

To apply for this offer or any travel credit cards, please use the links in this post or the CREDIT CARDS links in the main menu shown in the image below. These allow us to earn a commission — at no cost to you — to support our small business! Thank you!

credit cards link


5) Pay with Plastiq

plastiq pay taxes

While ordinarily, you CANNOT pay your taxes with a credit card, Plastiq makes it possible.

By paying your taxes with a credit card (which you will pay off within 30 days to avoid high-interest charges, right?), you can accrue points or miles depending on the card you use.

For example, you could earn Chase Ultimate Reward points by paying with the Sapphire cards or Chase Freedom, whose points can then be transferred to Southwest Airlines or British Airways (and other airline and hotel brands), for free travel.

Alternately, you could use your Southwest credit card to earn Southwest points directly.

If you pay with your Southwest credit card, the points earned via the card DO qualify for the Southwest Companion Pass.

Plastiq charges a 2.85% (or less) fee for the ability to pay bills like taxes, a mortgage, rent or a car payment with a credit card.

Does that soften the blow a bit? I hope so!

Here’s hoping you get a refund this year ;-).

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