Starting Point for 11am, 11:30am & 12pm Daytime Chicago Food Tours only. Your adventure begins at our designated starting point for the daytime tours, where you'll meet your lively, story-loving guide ready to dish out Chicago’s legendary history and hilarious local lore. Before you even take your first selfie at The Bean, you'll be diving into a bubbling, cheesy, deep-dish pizza—oozing with flavor and stacked with that signature stuffed crust magic. If you're looking for unforgettable Things to Do in Chicago, this Food Tour in Chicago is your first bite of something amazing.

Starting Point for 5:30pm Evening Tours only. The 5:30pm evening tour kicks off at the legendary Gino’s East, where your vibrant guide sets the tone with a lively intro to Chicago’s epic history—full of grit, glory, and a few wild tales. Then comes your first delicious bite: a bubbling, golden, cheesy deep-dish pizza that’s been winning hearts since the '60s. It’s the ultimate start to a Chicago Food Tour that serves up iconic eats and jaw-dropping views. If you're looking for flavorful Things to Do in Chicago, this Food Tour in Chicago is the perfect way to taste the city as the sun goes down.

A true foodie knows—some of the best meals come wrapped in paper and bursting with history. Enter the Chicago-style hot dog: a masterpiece that’s anything but ordinary. It starts with a juicy, all-beef frankfurter, cradled in a soft poppy seed bun. Then comes the magic—yellow mustard, that unmistakable neon green relish, freshly chopped onions, tomato wedges, a crisp dill pickle spear, sport peppers for a little kick, and a shake of celery salt to bring it all together. And remember: in Chicago, ketchup isn’t just unnecessary—it’s forbidden. This isn't just a hot dog; it’s a cultural rite of passage. On our Chicago Food Tour, you'll taste this legendary street food where it was meant to be eaten—at an authentic local stand like Relish, tucked along Michigan Avenue. If you're looking for unforgettable Things to Do in Chicago, this Food Tour in Chicago will satisfy your appetite for flavor, local lore, and serious foodie cred. We rotate our hot dog partner to keep things juicy.

Get ready to sink your teeth into one of Chicago’s juiciest, messiest, most mouthwatering creations—the legendary Italian Beef sandwich. Thin-sliced, slow-roasted beef piled high on fresh Italian bread, dunked (or double-dipped, if you dare) in savory, herb-infused au jus, and topped with spicy giardiniera or sweet peppers. It’s bold, beefy, and unapologetically satisfying. On our Chicago Food Tour, we rotate between some of the city’s most iconic local spots—each with their own take on this beloved sandwich, so no two tours are ever exactly the same. That means one day you might be biting into a classic dipped beef with sweet peppers, and the next, a spicy giardiniera masterpiece that leaves you wiping your chin and begging for more. If you’re hungry for authentic flavor and one-of-a-kind Things to Do in Chicago, our Food Tour in Chicago serves up this hometown hero with a side of city pride.

AM Tours Only. Available on our AM tours only, this sweet stop takes you back to 1893, when the Palmer House Hotel baked up a decadent little square of history—the original recipe brownie, crafted especially for the Chicago World’s Fair. Rich, fudgy, and topped with glossy apricot glaze and crunchy walnuts, it’s a far cry from your average bake sale treat. This is the first brownie ever made, and it still holds up as one of the most indulgent bites in the city. For any foodie with a sweet tooth and a love of culinary origin stories, this legendary dessert is a must-try. Join our Chicago Food Tour and taste a piece of edible history—just one of the many delicious Things to Do in Chicago that make our Food Tour in Chicago truly unforgettable.

No trip to Chicago is complete without a handful of Garrett’s famous Chicago Mix popcorn—a wildly addictive sweet-and-salty combo that foodies can’t stop buzzing about. This iconic blend swirls rich, buttery caramel corn with bold, savory cheddar for a flavor mashup that hits every craving at once. It’s warm, melty, crunchy, and completely crave-worthy—the kind of snack that turns popcorn skeptics into full-blown fans. On our Chicago Food Tour, you’ll skip the long lines and dive straight into this hometown favorite. It’s one of those Things to Do in Chicago you didn’t know you needed… until you’ve tasted it. Join our Food Tour in Chicago and crunch into the city’s most legendary snack.

AM Tours Only. Millennium Park is Chicago’s modern-day town square—a vibrant, art-filled oasis in the heart of the city where locals and visitors alike come to relax, explore, and snap that perfect Bean photo. But it’s more than just pretty views. Built above a massive underground parking garage and rail yard, this urban marvel is a feat of design and city planning that turned an industrial eyesore into one of the most beloved public spaces in the country. On our Chicago Food Tour, you’ll walk through this iconic park as we serve up the stories behind its world-famous landmarks—like Cloud Gate, Crown Fountain, and the Jay Pritzker Pavilion—alongside legendary bites like deep-dish pizza and Garrett’s popcorn. If you're hungry for culture, scenery, and serious flavor, this stop is a highlight of our Food Tour in Chicago and one of the most satisfying Things to Do in Chicago.

AM Tours Only. Chicago’s Cloud Gate—better known as “The Bean”—is more than just a shiny selfie magnet. This gleaming, stainless steel sculpture in Millennium Park reflects the city’s skyline in a way that feels almost magical, warping buildings and clouds into surreal, photo-worthy shapes. It’s playful, artistic, and one of the most iconic landmarks in the city. On our Chicago Food Tour, you won’t just snap a quick pic—you’ll learn the fascinating story behind this modern marvel while enjoying some of the city's most legendary bites. Pairing deep-dish pizza, hot dogs, and sweet treats with must-see sights like The Bean makes this Food Tour in Chicago one of the most flavorful and fun Things to Do in Chicago. Come hungry, leave inspired.

AM Tours Only. The Chicago Theatre isn’t just a pretty marquee—it’s the city’s crown jewel of entertainment history. With its dazzling lights and grand French Baroque architecture, it’s one of the most photographed buildings in Chicago. But here’s a bit of insider scoop: the massive “CHICAGO” sign out front? It’s not original—it was added in the '80s during a major restoration to match the theater’s golden era glam. On our Chicago Food Tour, we pass right by this show-stopping landmark while serving up the stories behind its legendary stage and the stars who’ve performed there. Paired with iconic eats like deep-dish pizza and Italian beef, this stop adds a dash of vintage flair to your flavor-packed journey. For foodies and culture-lovers alike, this Food Tour in Chicago hits all the right notes on the list of must-do Things to Do in Chicago.

Stretching through the heart of downtown, Chicago’s Magnificent Mile on Michigan Avenue is more than just a shopper’s paradise—it’s a stunning showcase of architecture, energy, and iconic city vibes. Lined with historic landmarks, glittering skyscrapers, and world-class boutiques, this bustling boulevard tells the story of Chicago’s rise from the Great Fire to greatness. As you walk this famed stretch on our Chicago Food Tour, you’ll experience the city the way it was meant to be explored—on foot, with flavor. Between bites of deep-dish pizza, Italian beef, and other local favorites, you’ll stroll past landmarks like the Tribune Tower, the Wrigley Building, and the start of historic Route 66. It’s the perfect blend of food, fun, and history—all wrapped up in one of the most exciting Things to Do in Chicago. So come hungry and curious—our Food Tour in Chicago will show you the Mile in a way that’s truly magnificent.

PM Tours Only. Chicago’s Historic Water Tower stands as a rare survivor of the Great Chicago Fire of 1871—a limestone Gothic beauty that looks more like a fairytale castle than a piece of city infrastructure. Built to house a water pump that once powered the city’s water system, it’s now a powerful symbol of Chicago’s resilience and rebirth. And here’s a fun tidbit: it’s one of the only buildings that made it through the fire while nearly everything else around it turned to ash. On our Chicago Food Tour, you’ll pass this iconic landmark as we journey through the city’s rich history and legendary eats. Between bites of hot dogs, Italian beef, and deep-dish pizza, you’ll hear how this small but mighty tower earned its place in Chicago lore. For a blend of flavor and fascinating stories, this Food Tour in Chicago is one of the most memorable Things to Do in Chicago—where every stop tells a tale.

AM Tours Only. Crown Fountain in Millennium Park is one of Chicago’s most unique public art installations—a pair of towering glass block fountains that project the faces of real Chicagoans, slowly changing expressions before playfully spitting water in the summer months. Designed by Spanish artist Jaume Plensa, it’s a blend of technology, art, and just the right amount of whimsy. On our Chicago Food Tour, you’ll experience this interactive landmark as part of your flavorful journey through the city’s heart. Between bites of deep-dish pizza and legendary local snacks, you’ll learn the stories behind the art that makes Chicago truly special. For a mix of fun, flavor, and photo ops, this Food Tour in Chicago is one of the most refreshing Things to Do in Chicago—especially if you don’t mind a little splash.

The Wrigley Building is a true Chicago stunner—an architectural gem that sparkles along the Chicago River with its white terra cotta façade and gleaming clock tower. Built as the headquarters for the Wrigley chewing gum empire, it was actually the city’s first air-conditioned office building—pretty cool, literally and historically. On our Chicago Food Tour, you’ll take in this iconic building from the best vantage points as we explore the Loop and Riverwalk, all while savoring Chicago’s most famous flavors. It’s the perfect blend of visual wow-factor and culinary indulgence. If you’re craving Things to Do in Chicago that feed both your curiosity and your appetite, our Food Tour in Chicago delivers the full experience—bite by beautiful bite.

PM Tours Only. Chicago’s Holy Name Cathedral is a stunning example of Gothic Revival architecture—and a spiritual and historical landmark with a dramatic backstory. Built in the 1870s after the Great Chicago Fire, it’s not just a place of worship, but a cornerstone of Chicago’s rebirth. And here’s an insider detail: just outside the cathedral, you can still see a small bronze cross marking the exact spot where a notorious mobster was gunned down during Chicago’s gangster era. History and mystery, all in one stop. On our Chicago Food Tour, you’ll pass this majestic cathedral as we explore the city’s rich cultural layers—paired with iconic bites like Italian beef, Chicago-style hot dogs, and that famous deep-dish pizza. If you're looking for Things to Do in Chicago that blend flavor, architecture, and untold stories, our Food Tour in Chicago offers a deliciously different way to experience the Windy City.

AM tours only. The Jay Pritzker Pavilion is Millennium Park’s architectural showstopper—a sweeping steel structure designed by world-renowned architect Frank Gehry. With its flowing curves and state-of-the-art sound system, it’s not just a concert venue—it’s a visual and acoustic masterpiece. Fun insider tip: the crisscrossing trellis above the lawn isn’t just for looks—it actually carries sound evenly to every seat, so even picnickers way in the back get front-row quality audio. On our Chicago Food Tour, you’ll stroll past this striking landmark as we blend art, architecture, and unforgettable eats into one delicious experience. Paired with bites like deep-dish pizza and Garrett’s popcorn, the Pavilion is just one of many iconic stops that make this Food Tour in Chicago one of the best Things to Do in Chicago—where the sights are as satisfying as the flavors.

The Chicago Loop is the vibrant heartbeat of the city—where dazzling architecture, rich history, and the hum of daily life all collide in one unforgettable downtown experience. Surrounded by the elevated “L” tracks, this iconic district is home to legendary theaters, historic skyscrapers, and can’t-miss sights like the Art Institute, Millennium Park, and the Chicago Riverwalk. On our Chicago Food Tour, you won’t just walk through the Loop—you’ll taste your way through it. As we explore its bustling streets and hidden gems, you’ll indulge in Chicago’s most famous eats, from deep-dish pizza to the original brownie. It’s a full-sensory experience that blends the flavors of the city with its most fascinating stories. If you're looking for Things to Do in Chicago that offer both epic eats and epic views, our Food Tour in Chicago through the Loop delivers bite after unforgettable bite.

When the weather cools down, we keep things warm and wonderful by taking you through one of Chicago’s best-kept secrets: the Pedway. This underground network of tunnels, bridges, and concourses weaves beneath the city’s central business district, connecting famous landmarks while keeping you cozy. On warmer days, we take the scenic route above ground, strolling the grand promenades of the Loop with the sun on your shoulders and the skyline soaring above. No matter the season, our Chicago Food Tour moves at a relaxed, comfortable pace—just 1.25 miles over 3 hours—with plenty of delicious stops and Instagram-worthy views. Whether you’re staying toasty underground or soaking up summer sights, this Food Tour in Chicago is a flavorful journey through the city’s history, culture, and iconic eats. If you're looking for unique and delicious Things to Do in Chicago, let us guide you through the streets—and tunnels—where the real magic happens.

FREE 2 HOUR BIKE or KAYAK RENTAL INFO: As an additional perk for booking this particular Chicago Food tour, you will get a FREE 2-hour bike or kayak rental (to be used within (+/-) 3 days of your tour booking. Terms below: To be used within +/- 3 days of your tour booking. Bike rentals take place at Bobby’s Bike Hike World Headquarters, 540 N. Lake Shore Drive, Chicago, IL60611. Bike shop is open year-round (excluding Thanksgiving & Christmas). Explore the 20 mile Lakefront Bike Trail, named Best Things to Do in Chicago. Kayak rentals take place at Ohio Street Beach, Bobby’s Kayak, 550 E. Grand Avenue, Chicago, IL 60611. Kayak shop open mid-May to mid-October, weather dependent. Offer excludes Saturday Bike/Kayak rentals between Memorial Day (end of May) Weekend to Labor Day (early September). Kayaking only available from June-September). Kayak on Lake Michigan. No discounts for not using this activity or issues due to weather restrictions.