Win $5,000 in the Simon® Back To School Sweepstakes — Here’s How

What if I told you that back-to-school shopping could literally pay off with a $5,000 payday? That’s exactly what Simon® is dangling in front of savvy shoppers with their latest high-stakes promo: the Simon® Back To School $5,000 Sweepstakes. If you’ve ever wandered through a Simon mall thinking, “Why isn’t someone paying me for this?”, well, now someone is.

This giveaway isn’t some flimsy coupon code. It’s a $10,000 prize pool, headlined by a massive $5,000 grand prize—and yes, it’s totally free to enter. You can even double dip and enter twice, if you know where to look (spoiler: we’ll show you). Keep reading, because this is one of those legit sweepstakes with real winners and real cash—no sketchy survey traps or app downloads required.

Let’s break it all down glam-style. No fluff. Just facts, links, and high-RPM content that’ll put this post on your Discover feed.

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🎁 Prize Breakdown: What Can You Win?

This isn’t a game of mystery boxes—you know exactly what’s up for grabs, and it’s straight cash via prepaid cards. Here’s the full breakdown:

• Grand Prize (1 winner): A fat $5,000 in prepaid cards. Total flexibility, no strings attached. Load up your digital wallet, pay bills, or splurge like the main character you are.
• First Prizes (10 winners): Each winner gets a $500 prepaid card. That’s enough for a major back-to-school haul, a mini getaway, or a debt detox.

💰 Total Prize Value: $10,000
All prepaid cards come with standard terms and expiration dates, so if you win, don’t let it collect dust in your junk drawer. Use it before it ghosts you.

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💸 What You Can Do With the Prize If You Win

Let’s not be boring about it. If you snag the $5,000, you’re not just winning money—you’re unlocking options.

Back-to-School Parents: Cover backpacks, laptops, shoes, and lunchboxes for the entire crew and still have leftovers for a Target run or two. That $5K stretches far when you plan it right.

College Students: Tuition looming? Rent draining your wallet? Use it to cover your books, lab fees, or stock up your dorm with essentials (and by essentials, we mean a mini fridge and 7 bags of frozen dumplings).

Hot Girl Side Hustlers: Need a new MacBook? Want to invest in a branding shoot? Planning to finally ditch Canva Pro for Adobe Creative Cloud? $5K puts you ahead.

Single Girl Era? Book the damn flight. Go full Eat, Pray, Love. Use that prepaid card to unlock your European summer—or a staycation with mimosas and massage oil.

Even if you “only” win the $500 prize, it’s still free money. Add it to your emergency fund, use it to pay down that Afterpay cycle, or finally replace your cracked phone screen. Do you. But do it with money someone else gave you.

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❓ Q&A: Everything You Need to Know

Is this legitimate?
Yes. The sponsor is Simon Management Associates II, LLC—aka the real-deal parent company behind Simon® Malls, Premium Outlets®, and more. This isn’t run by some mystery third-party. The promotion is being managed by Merkle Inc., a well-known administrator in the sweepstakes industry.

How many entries are allowed?
You can enter up to two (2) times—once on each site.

That’s it. Two max. Don’t try to hack it with fake emails—they’re watching.

Are there bonus entries?
Nope. No social sharing. No referrals. Just the two standard entries via the official forms.

How many prizes can you win?
Just one per person. If your name gets drawn for multiple prizes, they’ll award you the higher-value one and draw another person for the other. Fair game.