If you're a big holiday shopper, you're probably a fan of Cyber Monday.

The annual shopping holiday brought in an estimated $11.3 billion in sales in 2022, and is now the biggest online sales day of the year.

Keep reading to learn more about Cyber Monday, its origins, and how you can take advantage of Cyber Monday deals.

A person shops on their laptop for holiday gifts.
Image source: Getty Images.

When is Cyber Monday?

When is Cyber Monday?

Cyber Monday traditionally takes place the Monday after Thanksgiving. It's part of a five-day holiday weekend that kicks off the holiday shopping season.

Black Friday, the day after Thanksgiving, is typically the busiest shopping day of the year, and other "shopping holidays" have emerged to fill out the weekend.

The Saturday of that weekend, for example, is now known as Small Business Saturday, encouraging consumers to support small businesses, and the day after Cyber Monday is called Giving Tuesday to promote donations to non-profits.

What is the history of Cyber Monday?

What is the history of Cyber Monday?

Much like Black Friday before it, Cyber Monday has emerged as a day for Americans to do their online holiday shopping.

The shopping holiday actually developed somewhat organically. Americans who were fresh from a long weekend that likely included some window shopping and in-store holiday purchases continued to do so when returning to work on Monday.

That Cyber Monday happens on a workday was a natural fit since it allowed office workers to participate in it. The shopping bonanza dates back to the pre-smartphone era and a time when office workers may have had faster internet connections at work than they did at home with their own internet service providers, so it was easier to do their online shopping at the office.

By the mid-2000s, online retailers had noticed that the Monday after Thanksgiving had become one of the busiest online shopping days of the year.

In 2005, the National Retail Federation's Ellen Davis coined the term "Cyber Monday," and the shopping holiday has gained momentum since, embraced by both retail giants, such as Amazon (AMZN 3.43%) and Walmart (WMT -0.08%), and independent shops, such as Shopify (SHOP 1.11%) sellers, as a day to offer discounts and win over holiday shoppers.

How can you take advantage of Cyber Monday?

How can you take advantage of Cyber Monday?

Cyber Monday exists to offer shoppers one-day savings on online merchandise, so it's a good idea to have a strategy to save and score the best deals.

You'll want to sign up for store newsletters, so you know what's on sale. If there's a particular item that's got your fancy, it's a good idea to use a comparison shopping app like PayPal's (PYPL 2.9%) Honey to find the lowest price available for it. These tools can also let you know about promo codes that help you save even more money.

The ability to use these types of digital tools is one advantage of shopping on Cyber Monday vs. Black Friday since it's harder to comparison-shop in a physical store.

Often, Cyber Monday is a good opportunity to get savings on big-ticket items like electronics and furniture, and you can even find deals on travel like cruises and hotels.

Finally, if you're shopping for the holidays, it's a good idea to come prepared with a shopping list and a budget so you can make sure you meet all your needs without breaking the bank.

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What Cyber Monday looks like at one major retailer

What Cyber Monday looks like at one major retailer

It shouldn't come as a surprise that Amazon is a major participant in Cyber Monday. The e-commerce giant already owns roughly 40% of online sales in the U.S., and it's clearly a believer in the shopping holiday strategy -- it's even invented its own shopping holiday, Prime Day.

Cyber Monday is now a three-day event at Amazon, from Saturday to Monday. Among the deals Amazon offered last Cyber Monday were 70% off Alexa-enabled devices, 60% off Ring home security devices, discounts of as much as 50% on Gap merchandise, and 40% off on Mr. Coffee coffeemakers.

Cyber Monday results are a good barometer for the overall economy since consumers are shopping almost entirely for discretionary items. Keep your eye on Cyber Monday results this year. A strong performance could be a sign that a new bull market is coming soon if one hasn't started already.

John Mackey, former CEO of Whole Foods Market, an Amazon subsidiary, is a member of The Motley Fool’s board of directors. Jeremy Bowman has positions in Amazon, PayPal, and Shopify. The Motley Fool has positions in and recommends Amazon, PayPal, Shopify, and Walmart. The Motley Fool recommends the following options: short December 2023 $67.50 puts on PayPal. The Motley Fool has a disclosure policy.