Cyber Monday

10 Surprising Deals, Tips and Tricks for Cyber Monday

Keep an eye out for unconventional deals -- and deals that aren't really deals at all.
10 Surprising Deals, Tips and Tricks for Cyber Monday
Image credit: JGI | Tom Grill | Getty Images
Entrepreneur Staff
7 min read

If you aren’t tired out or broke from all of the Black Friday sales that began popping up online days before Thanksgiving, get ready for Cyber Monday, the biggest U.S. online shopping day of the year.

Cyber Monday is a phenomenon that arose in the 2000s, when deal-seekers would return to work after a weekend of shopping and snag discounts online using their employers’ internet connections. National Retail Federation Senior Vice-President Ellen Davis and former Shop.org Executive Director Scott Silverman coined a term for the trend in 2005. Retailers adopted it, and the rest is history.

Related: The Best Black Friday Deals of 2017 From Amazon, Best Buy, Target and More

Most Americans have an internet connection on their phones that surpasses what they could get at work a decade ago. Last year, online sales on Cyber Monday totaled $3.39 billion nationally, surpassing Black Friday U.S. online sales by about $50 million, according to Adobe Digital Insights.  

This Monday, Nov. 27, heat up the last of your turkey day leftovers, fire up your smartphone, social media apps and/or web browser and prepare to find the best promotions from not just big-box stores, but travel sites, online learning platforms and more.

Click through to learn how to score the best deals on Cyber Monday -- and how you can prepare for the big day in advance.

Related: 4 Easy Steps to Marketing Your Local Business Online

10 Surprising Deals, Tips and Tricks for Cyber Monday

Book a trip.

Book a trip.
Image credit: Hotel Commonwealth

Millennials value experiences over things, so goes the generational stereotype. But, regardless of age, anyone can benefit from discounted getaways. On Cyber Monday, head to travel booking or hotel websites to search for discounts on trips to destinations near and far. If there’s a specific hotel or resort you’ve been longing to stay at, it might be worth opening a new tab in your browser and seeing it has any promotions around the Thanksgiving weekend shopping holidays.

For example, the Hotel Commonwealth in Boston is offering rooms for $100 from 10 a.m. until 11:40 a.m. Eastern (a 100-minute period) on Cyber Monday. (Last year, it offered $127 rooms over a 127-minute period.) There are also deals out there for private islands and even private jets.

Make sure that you’re actually getting a deal, though: Do your research beforehand and get a feel for the market so you don’t fall for a price that’s labeled as a discount without actually being one. Same goes for reading the fine print on any restrictions, which you should always do anyway, of course.

Related: 10 TSA-Approved Travel Tips to Make Your Holiday Travel Easier

10 Surprising Deals, Tips and Tricks for Cyber Monday

Use rewards apps.

Use rewards apps.
Image credit: RetailMeNot

If you’re not already using apps such as Ebates and Shopkick to get coupon codes and cash back on purchases, consider downloading one of them before you spend big on Cyber Monday. Ebates offers new members $10 in credit when they make a purchase, and after you spend $25 via the app, you can refer a friend for an additional $25 bonus. RetailMeNot is another app that has rounded up deals and cash-back opportunities.

Shopkick users earn points, or “kicks,” when they walk into stores or visit retailer websites, make purchases or scan products with their phone. Kicks add up to rewards such as gift cards or credit to donate to charity. On Cyber Monday, Shopkick is offering 10 kicks for every $1 a user spends at online retailers including Walmart.com, eBay, Groupon, Hotels.com, Booking.com, Boxed, SeatGeek and Minibar.

Related: How Retailers Are Thriving Despite the Supposed Death of Their Industry
10 Surprising Deals, Tips and Tricks for Cyber Monday

Install free browser plug-ins.

Install free browser plug-ins.
Image credit: Honey

Along those lines, browser extensions such as Honey will generate coupon codes automatically at checkout. CouponFollow’s Cently app works similarly, while InvisibleHand displays a pop-up bar notifying you when you can get a better deal elsewhere (from 696 retailers and 589 airlines), in real time.

Always remember that these types of third-party apps aren’t error-free, however. Before making purchases, double-check that the codes and coupons you’re trying to use actually have gone through.

Related: The 100 Best Free Google Chrome Extensions

10 Surprising Deals, Tips and Tricks for Cyber Monday

Keep an eye on your social feeds.

Keep an eye on your social feeds.
Image credit: DealNews

Coupons and deals can pop up anywhere, and that includes on social media. From ads to posts by your favorite brands, you might stumble upon a promo code as you scroll, advises DealNews (which also has an app to keep you abreast of the latest promotions). So, take a break from juggling shopping and work on Cyber Monday to check your apps.

Who knows? A Facebook friend or someone you follow on another platform might generously share info about a sale or deal.

Related: 4 Social Media Trends You Need to Know About for Next Year

10 Surprising Deals, Tips and Tricks for Cyber Monday

Buy toys

Buy toys
Image credit: Hasbro

Have some holiday shopping for the little ones in your life on your to-do list? Get it done early. Cyber Monday will be the best day of the week surrounding Thanksgiving to buy toys, according to Adobe Digital Insights.

Tap into nostalgia by buying old-school toys for members of the younger generations: Adobe reports that Nerf Guns, Teddy Ruxpin and Super Nintendo Classic have been buzzy topics on social media over the past few months.

While Cyber Monday will bring deals in other categories, Adobe predicts that Thanksgiving will be the best day to save money on computers, tools, sporting goods, video game consoles and apparel, while Black Friday will be ideal for purchasing appliances and gadgets. If you’re looking for home decor, wait until Giving Tuesday.

Related: Best Cyber Week Electronics Deals at Amazon

10 Surprising Deals, Tips and Tricks for Cyber Monday

Learn something new.

Learn something new.
Image credit: Udemy

You don’t have to wait until Cyber Monday for this deal: Now through Nov. 28, online learning platform Udemy is offering discounts on its 55,000-plus courses. Use the code "17HOLIDAY10" to take courses on everything from coding to drawing to financial analysis -- for $10 a pop. Many of the courses Udemy has discounted normally cost between $50 and $200.

Courses that might come in handy for entrepreneurs include those that teach interviewing skills or productivity and time management.

Related: 10 Udemy Courses Under $100 That Could Help You Make $1,000 (or More)

10 Surprising Deals, Tips and Tricks for Cyber Monday

Use an incognito window.

Use an incognito window.
Image credit: Google

Your web-browsing history on any of your devices affects the ads, search results and even prices you see. To level the playing field on Cyber Monday, clear your cookies by using an incognito window (or whatever your browser’s equivalent is) to shop anonymously. Plus, block the browser from knowing your location if prompted, or turn off location tracking in its settings.

Related: How to Spy on Your Competitors to Outrank Them on Google

10 Surprising Deals, Tips and Tricks for Cyber Monday

Pre-load your shopping cart.

Pre-load your shopping cart.
Image credit: Bet_Noire | Getty Images

If you have time over the long weekend, start scoping out deals and filling your online shopping carts with items ahead of Cyber Monday. That way, when the promotions go live, you’ll be ready for checkout. Just make sure that your purchase price matches the deal you’re seeking before you click the buy button. If you want to be really ready for action, add alternative products in case your first choice sells out immediately. (Same goes for Black Friday or any sales announced in advance.)

Related: 12 Awesome Tips From Ecommerce Experts

10 Surprising Deals, Tips and Tricks for Cyber Monday

Create store accounts in advance.

Create store accounts in advance.
Image credit: Oscar Wong | Getty Images

Many online retailers ask you to sign in to make a purchase. If you have personal accounts with stores ahead of Cyber Monday, and know the password for each, you’ll be set for a smooth checkout process, because your address will already be in their system.

Stores want to know you’re interested, and many of them will send you newsletters with details about sales once you have an account. You may even get a special discount for opting in to an email list.

Related: More Emails, More Sales? The Surprising Argument For Aggressive Email Marketing.

10 Surprising Deals, Tips and Tricks for Cyber Monday

Use a single credit card for all of your purchases.

Use a single credit card for all of your purchases.
Image credit: Sofie Delauw | Getty Images

You never know when hackers will strike, but major shopping days are certainly high-risk. If you pay for all of your purchases with the same card, you won’t have to cancel multiple if your payment information is stolen. Better yet, make it a credit card with fraud protection.

Related: Cyber Monday 2017: Everything You Need to Know

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  • 10 Surprising Deals, Tips and Tricks for Cyber Monday
  • 1. Book a trip.
  • 2. Use rewards apps.
  • 3. Install free browser plug-ins.
  • 4. Keep an eye on your social feeds.
  • 5. Buy toys
  • 6. Learn something new.
  • 7. Use an incognito window.
  • 8. Pre-load your shopping cart.
  • 9. Create store accounts in advance.
  • 10. Use a single credit card for all of your purchases.
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