🎒Self-Guided Chicago Food Tour, Free Fun in the City & a Vacation Scam You Need to Know About
Chicago—land of deep-dish dreams and skyline scenes. I recently did a self-guided food tour through the city and discovered that you don’t need a pricey guide to eat your way through some of the best bites in town. And guess what? I also found some seriously cool free things to do in Chicago that made my trip both budget-friendly and amazing. But before we get to the good stuff, let me share a quick cautionary tale. Because not all “free” trips are created equal—and my experience might save you hundreds of dollars and hours of your life.

🚨 The “Free” Vacation Scam: What Really Happened
My boyfriend and I were stoked when we won a trip to Jamaica, Mexico, or Puerto Rico from 99JAMZ Miami. I mean, who wouldn’t be? A free tropical getaway! Except… it wasn’t really free.

First red flag? They asked for $99 to “secure” the trip. Then came the catch—you had to attend a timeshare presentation two hours from our home. Fine, we thought. We’ll sit through it and get our vacation.

That two-hour drive turned into a 6-hour ordeal (including the meeting), plus $60 in gas. The salespeople were aggressive and persuasive. We didn’t buy into the timeshare, but many people did. And that was just the beginning.

Now we had to deal with a company called GRCVO. More fees followed—$199 for “taxes and fees,” then $478 more for mysterious “agency and hotel charges.” When we asked for itemized receipts or basic booking info, we got nothing but dodges. No help with flights, no clear hotel details, and no refunds.

In the end, we paid $836—more than the trip was worth—and lost about 12 hours of our lives. This trip was a scam wrapped in a bow of “convenience” and “luxury.” If you ever get one of these offers, do not give them money. Run. Report it. And let this be your warning.

🥪 Self-Guided Chicago Food Tour: The Delicious Way
Okay, on to the good stuff! Chicago is a food lover’s playground, and you can create your own food tour without spending a fortune. Here’s how I did it:

🧀 1. Start with Deep Dish
Where: Lou Malnati’s or Pequod’s

Why: You can’t visit Chicago without trying their legendary deep-dish pizza.

Pro Tip: Split one with a friend. They’re dense!

🌭 2. The Chicago Dog
Where: Portillo’s or Gene & Jude’s

What to expect: A no-ketchup, fully-loaded hot dog that’s basically a food group in itself.

🌮 3. Taco Time
Where: Taqueria Chingón (Logan Square)

Why: Because Chicago’s Mexican food scene is 🔥 and often overlooked.

🍩 4. Sweet Treats
Where: Do-Rite Donuts

Pick: The buttermilk old-fashioned or their vegan options.

☕ 5. Coffee Break
Where: Sawada Coffee (West Loop)

What: A military latte or matcha-based drink with espresso and creativity.

🎉 Free Things to Do in Chicago That Are Actually Fun
This city knows how to entertain—even on a $0 budget.

🖼️ 1. Art Institute of Chicago (Free Days)
Illinois residents get in free on select weekdays. Even if you’re not a local, watch for museum passes at libraries or CityPASS discounts.

🏙️ 2. Millennium Park
It’s not just about “The Bean.” You’ll find art installations, live music, and incredible views.

🚶 3. The 606 Trail
A converted elevated rail line that’s now a scenic walking/biking path through some of Chicago’s coolest neighborhoods.

🌊 4. Chicago Riverwalk
Free to walk, great views of the architecture, and you might even catch a street performance or pop-up art show.

🎷 5. Free Concerts & Festivals
Check the city calendar for events at Grant Park or Navy Pier. Summertime Chi = endless vibes.

✨ Final Thoughts
Travel can be delicious, affordable, and unforgettable—but it can also come with shady strings attached if you’re not careful. I hope my experience helps you make the most of your trips and avoid the scams that try to steal your joy (and your wallet).

So go ahead: Eat your way through Chicago, dance to some free jazz in the park, and keep your eyes open for deals that are too good to be true.