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Overview

Chicago doesn’t whisper its flavors—it shouts them from skyscrapers and street corners. This immersive walking food tour blends the city’s most iconic eats with inventive local sips for a bold culinary journey through the Windy City’s rich layers.

Start under the soaring spires of the Harold Washington Library before diving headfirst into Chicago’s flavor hall of fame. From a hot dog that refuses ketchup to an Italian beef sandwich dripping with juicy pride, you’ll hit all the heavyweight bites—including deep-dish pizza so thick it could hold up traffic on the Dan Ryan.

But it’s not just about what you eat—it’s how you pair it. Add the drink upgrade to elevate your experience: sip a locally brewed Goose Island 312 Urban Wheat Ale, light and golden like a Lake Michigan sunset. Then unwind with the Brownie Old-Fashioned, a daring twist on a classic cocktail with rich chocolate notes that nod to the city’s sweet claim to fame.

From popcorn Oprah can’t resist to a secret treat hidden in the shadows of the Willis Tower, this tour is more than a meal—it’s a love letter to Chicago, served one iconic flavor at a time.

Approximately 3 hours of food and drink pairings led by a local tour guide
Curated tastings across six iconic stops:
- Stop 1 – Where Stories Reach New Heights
  Start your journey at the Harold Washington Library, a striking postmodern landmark celebrating Chicago’s literary and civic legacy. Your guide sets the stage with tales of transformation, ambition, and the towering spirit that shaped the city’s skyline—and its flavors.
- Stop 2 – Popcorn with a Celebrity Seal
  Your next bite is a Windy City favorite made famous by Oprah’s personal stamp of approval. Dig into a sweet-and-savory medley of gourmet popcorn—cheddar, caramel, and buttery bliss—all mixed into one crave-worthy Chicago classic.
- Stop 3 – A Hot Dog That Breaks the Rules
  Savor a true Chicago-style dog—fully dressed in yellow mustard, neon relish, diced onions, sport peppers, tomato wedges, a dill spear, and a sprinkle of celery salt, all cradled in a poppy seed bun. And yes, still no ketchup allowed.
- Stop 4 – A Skyscraper Secret Worth the Climb
  Stroll past the legendary Sears (now Willis) Tower and discover a hush-hush specialty tucked nearby. This crispy, savory snack is one of the city’s lesser-known bites—local-loved and off the tourist radar.
- Stop 5 – The Iconic Italian Beef Moment
  Sink your teeth into one of Chicago’s most beloved sandwiches: slow-roasted Italian beef, sliced thin and soaked in rich jus. Add giardiniera for a spicy kick and prepare for a gloriously messy—and deeply satisfying—experience.
- Stop 6 – Deep-Dish and a Decadent Dessert Twist
  Close the tour with a piping-hot slice of deep-dish pizza, piled high with mozzarella, zesty tomato sauce, and a flaky, golden crust. Then, finish with a tribute to a local invention—the brownie—given a bold, modern makeover.
Signature Drinks Included:
- Goose Island 312 Urban Wheat Ale
- Brownie Old-Fashioned

Full Description

Total Duration: Approximately 3 hours of bold bites, local pours, and neighborhood stories from across Chicago’s dynamic food scene.

Tour Format:

Meet your local guide and set off on a flavorful walk through vibrant streets and under-the-radar gems that reflect the city’s diverse culinary roots.
Visit six curated stops—featuring everything from legendary popcorn and no-ketchup hot dogs to deep-dish pizza and a sweet local invention, each paired with a standout bite or drink.
Along the way, connect with fellow food enthusiasts, hear surprising food lore, and sip your way through Chicago’s creative cocktail and craft beer scene.

Group Size: Designed for 2 to 12 participants to keep things intimate, interactive, and fun.

Photography: From beautifully plated dishes to eye-catching drinks and striking city scenes, you’ll find plenty of moments worth snapping.

Foodies chasing Chicago’s legendary bites—and its best-kept secrets
Couples looking to mix deep-dish cravings with craft cocktails
Groups of friends and families searching for something fun, flavorful, and off the usual path
Locals who know there’s always another layer to the city’s food scene
Celebration crews raising a toast to birthdays, milestones, or just being in Chicago
Drink lovers eager to sip local

Not just another food tour—this is Chicago served real, raw, and unforgettable.

Availability

Important Information

In collaboration with Cozymeal, ThrillGifts invites you on a Chicago food tour that peels back the layers of the city’s legendary food scene. With a local expert leading the way, you’ll taste your way through neighborhood staples, unexpected finds, and the untold stories behind Chicago’s most iconic eats, crafted for flavor chasers, urban explorers, and anyone hungry for a deeper bite of the city.

Dietary Notes: The menus shift with the seasons, and while we’d love to accommodate everyone, most tours are unable to support specific dietary restrictions.
Pets: Though we're big animal lovers, this experience is not pet-friendly.
Private Tours: Ideal for birthdays, corporate outings, and milestone moments. Reserve in advance to lock in your preferred date.

Arrival: Please plan to arrive 10–15 minutes early for a hassle-free check-in.
Location & Parking: This tour takes place in Chicago. Parking instructions and meeting point details will be provided in your confirmation email.
What to Wear: Dress for the day’s weather, and wear comfortable walking shoes.
What to Bring:
- A refillable water bottle
- Your appetite
- A phone or camera for those picture-perfect moments
- Weather gear like an umbrella, hat, or sunglasses
- A valid photo ID if you plan to enjoy alcoholic drinks
Gratuity: Tips aren’t required but are always appreciated by your guide.

Location

This experience does not have a physical location and can be attended online.

This experience will be held at a location of your choice within the service area.

Chicago’s Signature Bites, Chicago

Flavors that built the city. Sips that bring it to life.

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How It Works

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Overview

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