(A Tale of a “Free” Trip That Cost Us $836 and Our Sanity)

By: [Your Name or Blog Name]

There’s a reason I now triple-check every “free vacation” offer.
Let me take you back to the moment my boyfriend and I thought we had scored the deal of a lifetime—and how we ended up paying $836.50, giving away 12 hours of our lives, and being manipulated by smooth-talking timeshare salespeople. Trust me, the free stuff in Chicago? Way more worth it.

🎙️ The “Free” Trip That Wasn’t

We were big fans of 99JAMZ Miami radio and one day, decided to call in for a chance to win a “free trip” to Jamaica, Mexico, or Puerto Rico. To our surprise, we won! But then came the catch: a $99 non-refundable “processing fee” to confirm our spot.

That was just the beginning.

Before we even saw the beach, we had to drive two hours from the Florida Keys to a timeshare presentation in Fort Lauderdale. The presentation alone was two hours, the drive cost us $60 in gas, and the pressure was unreal. Professional salespeople pushed pricey travel packages on people who just came for the “freebie.”

Then we met the real puppeteers behind the curtain: a company called GRCVO. They demanded another non-refundable $199 “deposit” to lock in our trip. We were already in deep, so we paid. Eventually, we were given a list of three hotels to choose from in Montego Bay. Depending on which one we picked, there’d be more fees. Surprise, surprise: they wanted another $478 to cover “agency fees, hotel fees, international taxes”—whatever that means.

And forget getting answers about flights, luggage, hotel upgrades, or airport transfers. The answer was always the same: “You have to call them directly.”
No help, no itemized invoice, and everything was non-refundable.

Total cost? $836.50.
The kicker? The average price for the same trip online? $833.

🚫 Moral of the Story: If a Trip Feels Like a Scam, It Probably Is

If you’ve ever been tempted by one of those “radio giveaway” vacations, RUN. File a complaint with the FTC, FCC, or your State Attorney General. And always, always read the fine print. Even if it’s technically legal, it can still be predatory.

Now, onto something that is actually free and doesn’t require a 6-hour presentation or hidden fees…

✅ Free Things to Do in Chicago That Are Actually Worth It

If you’re visiting Chicago (or live here and want to feel like a tourist for the day), here’s a list of genuinely free, 100% fun activities that won’t con you out of your money:

1. Stroll Through Millennium Park

The iconic Bean (a.k.a. Cloud Gate), Crown Fountain, and the Jay Pritzker Pavilion — all in one place. Come during summer for free outdoor concerts.

2. Lincoln Park Zoo

One of the few free zoos left in the U.S.! It’s charming, walkable, and perfect for an afternoon wander.

3. Chicago Cultural Center

Jaw-droppingly beautiful stained glass domes and rotating art exhibits. And yes, completely free.

4. Lakefront Trail

Grab your walking shoes or bike and cruise along 18 miles of shoreline with skyline and lake views that feel like a luxury experience—without the price tag.

5. Navy Pier Fireworks (Seasonal)

In the summer, catch fireworks shows at Navy Pier on Wednesdays and Saturdays. You don’t even have to go on the Pier — view them for free from many lakefront spots.

6. Free Museum Days

Many of Chicago’s world-class museums (like the Art Institute, Field Museum, and MSI) have free days for Illinois residents. Check their websites for updated info.

7. Garfield Park Conservatory

A lush, tropical escape right in the city. Perfect for cold winter days when you need a bit of warmth and green.

💬 Final Thoughts

You don’t need to fall for a “free vacation” gimmick to have a great time. Whether you’re a local or a visitor, Chicago has plenty of real, free adventures waiting for you—no catch, no fine print, no sketchy phone calls.

And if you’ve ever fallen for a travel scam like I did? You’re not alone. But the good news is, there’s a lesson in every journey.

Have a similar story or know of more free spots in Chicago? Drop a comment below — let’s help each other travel smarter.