Chicago—land of deep-dish dreams, jaw-dropping architecture, and food trucks that will change your life. I recently spent a whirlwind weekend exploring this vibrant Midwestern gem on a mission: eat well, spend little, and soak up as much of the city as possible—without booking a guided tour or blowing my budget. What started as a spontaneous adventure quickly became one of my favorite DIY travel experiences.

But before we dive into the cheesy goodness of deep-dish pizza and the serenity of riverside walks, I have to share a travel scam story that almost derailed our trip. If you’ve ever been tempted by a “free vacation” offer, read this first.

🚨 The “Free” Vacation Scam: A Cautionary Tale

It began with a phone call from a Miami radio station—99JAMZ. My boyfriend and I were ecstatic: we had supposedly won a trip to Jamaica, Mexico, or Puerto Rico. A free tropical escape? Sign us up.

Except, it wasn’t free at all.

⚠️ The Red Flags

• We were required to pay $99 to “secure” our trip.
• We had to attend a timeshare presentation two hours away.
• That presentation ended up lasting six exhausting hours.
• We spent $60 on gas and an entire day of our trip.
• The sales pressure was unbearable, with many feeling forced to sign.

Enter GRCVO—the booking company from hell.

Following our supposed win:

• We paid another $199 for taxes and service fees.
• Then $478 for vague “hotel and agency” charges.
• We received zero booking confirmations, no flight help, and no hotel info.
• Calls were dodged. Emails went unanswered.

Total damage: $836. For a vacation that never happened.

Lesson Learned:

If anyone asks you to pay for a “free” trip, RUN. Report them and protect your wallet. Because that money could be much better spent eating your way through a city like Chicago—which is exactly what we did next.

Chicago’s food scene is legendary, but you don’t need a luxury budget to indulge. Here’s how we savored some of the best bites in the city without emptying our pockets.

🧀 1. Deep Dish Pizza

• Where: Lou Malnati’s or Pequod’s (Lincoln Park)
• Why Go: Thick, buttery crust, layered cheese, and a rich tomato sauce you’ll dream about.
• Budget Tip: Split a small pie between two—you’ll still be stuffed.

🌭 2. The Chicago-Style Hot Dog

• Where: Portillo’s (Downtown) or Gene & Jude’s (River Grove)
• What Makes It Special: Mustard, relish, onions, tomatoes, sport peppers, a pickle, and NO ketchup.

🌮 3. Mexican Street Food

• Where: Taqueria Chingón (Logan Square)
• Must Try: Duck carnitas taco, house salsas, and seasonal specials.

🍩 4. Donut Heaven

• Where: Do-Rite Donuts (Loop or Streeterville)
• What to Expect: Vegan options, classic buttermilk, and delicious coffee pairings.

☕️ 5. Coffee With a Twist

• Where: Sawada Coffee (West Loop)
• Why Go: Try the Military Latte—a delicious combo of matcha, espresso, and cocoa.
• Pro Tip: Visit late morning to avoid the rush.

You don’t need to spend a dime to fall in love with Chicago. These free sights and events were some of the highlights of our trip.

🎨 1. The Art Institute of Chicago

• Free Days: Select weekdays for Illinois residents.
• Don’t Miss: Grant Wood’s American Gothic, Thorne Miniature Rooms, and the Impressionist collection.
• Bonus: CityPASS and library passes can offer free or discounted entry for others.

🌳 2. Millennium Park

• Iconic: Snap a selfie by Cloud Gate (aka “The Bean”) and enjoy live music, yoga classes, and art installations.
• Great For: Picnics, families, and urban nature seekers.

🚶️ 3. The 606 Trail

• What It Is: A 2.7-mile elevated park and trail system through Logan Square and Wicker Park.
• Tip: Look out for murals and coffee shops along the path.

🌊 4. The Chicago Riverwalk

• Scenic Bonus: Public art, pop-up vendors, and street performers.
• Cost: Free to walk; food and kayak rentals available if you want to splurge.

🎶 5. Free Festivals and Events

• Summer Picks: Grant Park Music Festival, Chicago Blues Festival, and Navy Pier fireworks.
• Stay Updated: Check the city’s official events page for free happenings.

This trip taught me that you don’t need to spend thousands to experience a city as rich and dynamic as Chicago. With a little planning, you can:

• Avoid scams that target eager travelers
• Enjoy Chicago’s legendary eats on a budget
• Discover free cultural and outdoor experiences

Whether you’re a foodie, an architecture buff, or just looking for a fun weekend escape, Chicago has something for you—no expensive tours required.

So here’s my advice: skip the “free vacation” calls, pack your walking shoes, and plan your own unforgettable adventure.

Planning your own Budget Chicago Weekend? Bookmark this post and share it with your travel buddy. Follow the blog for more DIY city guides, budget travel tips, and honest reviews from the road.