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Overview

Get to know Chicago the way locals do—through its food, its stories, and the neighborhoods that bring both to life. This walking tour blends the city’s iconic sights with its most beloved bites, giving you a taste of what makes Chicago truly unforgettable.

Kick things off at the Harold Washington Library, a striking landmark that sets the stage for what’s to come. Snack on buttery popcorn that Oprah made famous, grab a hot dog piled high with classic Chicago toppings (no ketchup here!), and dig into a juicy Italian beef sandwich that’s packed with flavor. You’ll also step into the Willis Tower for a surprise dish with a view, then wind down with a deep-dish pizza slice and a rich, reimagined brownie—originally invented right here in Chicago.

Whether you're visiting for the first time or rediscovering the city you call home, this tour is a fun, flavorful way to explore the best of Chicago—with plenty to eat, plenty to learn, and plenty to love.

A 3-hour food tour led by a professional guide
Curated tastings across six iconic stops:
- Stop 1 – Where the City’s Story Begins
  Kick off your tour at the Harold Washington Library, a postmodern icon topped with watchful copper owls. Your guide brings the city’s past into focus, sharing stories of innovation, resilience, and the people who helped build Chicago’s reputation as a capital of culture—and food.
- Stop 2 – Popcorn Worth the Hype
  Oprah put this one on the map, but locals have loved it for decades. Sample a signature mix of cheddar, caramel, and butter popcorn—sweet, salty, and impossible to put down.
- Stop 3 – The Classic That Refuses Ketchup
  A Chicago-style hot dog the way it was meant to be: loaded with yellow mustard, neon relish, chopped onions, tomato wedges, sport peppers, a dill pickle spear, and a dash of celery salt—served in a poppy seed bun. No ketchup. Ever.
- Stop 4 – A Hidden Bite Near a Towering Icon
  Pass by the world-famous Willis Tower and make a quick detour for a secret dish you won’t find in the guidebooks. This crispy, flavorful snack is a local favorite that flies under the radar—but leaves a lasting impression.
- Stop 5 – Chicago’s Favorite Mess
  Bite into a sandwich that’s both iconic and unapologetically messy: thin-sliced Italian beef slow-cooked in savory jus. Want it with a kick? Add spicy giardiniera, then grab extra napkins—you’ll need them.
- Stop 6 – A Deep-Dish Finish & a Dessert with Roots
  Close out the experience with a deep-dish pizza slice layered with bubbling cheese, chunky tomato sauce, and a flaky crust. Then, enjoy a fresh take on a Chicago-born invention—the brownie—served with a modern twist that honors its rich legacy.

Full Description

Total Duration: Around 3 hours of flavorful eats and authentic stories from Chicago’s ever-evolving culinary scene.

Tour Format:

Join your local guide for a delicious stroll through lively neighborhoods and hidden gems that showcase Chicago’s rich and varied food culture.
You'll visit six handpicked spots—from iconic popcorn and rule-breaking hot dogs to deep-dish favorites and a reimagined hometown dessert—each served with a memorable bite or sip.
As you explore, swap stories with fellow food lovers, uncover unexpected culinary trivia, and sample drinks from the city’s inventive beer and cocktail scene.

Group Size: Limited to 12 guests for a more personal, engaging, and enjoyable experience.

Camera-Friendly: With stunning dishes, vibrant drinks, and iconic city backdrops, you’ll have plenty of photo-worthy moments along the way.

Couples chasing a date night that breaks the mold
Friends and families hungry for a flavorful twist on the usual outing
Solo diners ready to connect over bites, stories, and unexpected laughs
Celebration crews toasting birthdays, reunions, or simply soaking up the city
Foodies on the hunt for iconic bites and off-menu surprises
Weekend explorers squeezing big flavor into a short city stay
Out-of-towners eager to skip tourist traps and eat like a local
Corporate teams mixing business with deep-dish and storytelling

Deep-dish, hot dogs, history—Chicago’s greatest hits, served hot.

Availability

Important Information

ThrillGifts, in collaboration with Cozymeal, maps out a Chicago few ever taste—but no one forgets. This isn’t your average food tour. It’s a guided walk through the city’s edible identity—led by a local who knows where the good stuff lives. From iconic bites like deep-dish and Italian beef to unexpected neighborhood gems, each stop layers flavor with story.

Dietary Information: Menus may change based on seasonal availability. Please note that most tours are not able to accommodate individual dietary needs at this time.
Pets: We love furry companions, but unfortunately, pets aren’t permitted on this tour.
Private Groups: Planning a birthday, team event, or special celebration? Private tours are available—be sure to book early to secure your preferred date.

Arrival Time: We recommend arriving 10–15 minutes early to ensure a smooth check-in.
Location & Parking: The tour takes place in Chicago. You'll receive detailed meeting point and parking info in your confirmation email.
What to Wear: Dress appropriately for the weather and wear comfy walking shoes.
What to Bring:
- A reusable water bottle
- Your hunger for great food
- A phone or camera for all those Instagram-worthy shots
- Weather essentials like an umbrella, hat, or sunglasses
- A valid photo ID if you’ll be enjoying alcoholic beverages
Gratuity: Tips are never expected but 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.

Discover Historic Chicago, Chicago

Chicago’s best bites, blocks, and backstories—served fresh.

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79

79

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How It Works

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Overview

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