Paying Taxes with a Credit Card in 2022

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Every year during this time, we reconcile our earnings and deductions for Uncle Sam and either fork over more dough or humbly request that a little be given back. If you follow the strategies of this blog you may not have much tax liability to begin with, but if you find yourself in a position where you owe the IRS and were wondering if you could earn rewards points on that payment, the answer is yes. More significantly, there’s an interesting trick where you can potentially earn hundreds of thousands of points and miles by making estimated payments which is discussed below.

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A Brief History of American Money

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Since time immemorial, humans have used items of perceived value to exchange for goods and services. Shells, stones, gold, gems, paper, and even lines of code as a digital currency are used to establish a common medium of exchange that is predicated on trust — if everyone agrees that a $100 bill is worth $100 then the system works, otherwise it is useless.

Last fall during a trip to Virginia, we stopped into the American Civil War Museum in Richmond. Among the many well-crafted displays was an excellent exhibit on the history of American money and how the currency we know and use today began as a result of the war.
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Transferring Chase Ultimate Rewards® to Hyatt for Maximum Value

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When planning for a recent weekend trip to Boston, I was poking around at the availability of hotels and found cash prices to be exceedingly high during our dates at $300+ per night. I scoffed at the idea of handing over $1,000 or more for a couple of nights away and instead turned to my trusty award miles to see if there was a most cost-effective approach.

As it turns out, I found a good deal on a centrally-located Hyatt property and was able to snag it for 8,500 points + $73 per night, a value of 3.8 cents per point as the cash prices were $398. In this post, I’ll explain how to transfer Chase Ultimate Rewards® to Hyatt for great value.
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Easily earn the Southwest Companion Pass + 30k Points

Advertiser Disclosure: This site is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as CardRatings.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.

One of the best deals in modern award travel is the Companion Pass offered by Southwest Airlines. With it, you can fly two passengers for the price of one on both paid and award flights, offering massive long-term value.

Though the Companion Pass has traditionally been difficult to earn (more on that below), Chase has increased the welcome bonus offers on the personal versions of their Southwest Rapid Rewards credit cards to enable earning it with just a single sign-up – and the deal ends March 14, 2022.
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Resort Report: Four Seasons Hotel, Chicago

Advertiser Disclosure: This site is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as CardRatings.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.

In an effort to reignite travel spending from its cardmembers, American Express released a slew of new benefits to their Platinum credit card in 2021 — one of which was a $200 yearly credit for prepaid hotels through the Amex Travel portal.

Finding ourselves in Chicago for a weekend gave us the opportunity to put this credit, and a new property, to the test at the Four Seasons. Here’s how it went.
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