Chicago Food Tour: 5 Classics with Local Guide

Chicago's five signature foods taste nothing like their chain versions.

This 3-hour walking food tour through downtown Chicago includes tastings of five local classics (deep-dish pizza, Chicago-style hot dog, Italian beef sandwich, Garrett's popcorn and a dessert) led by an English-speaking guide who shares the city's food history and architecture. You choose between a daytime tour (visiting Millennium Park, Cloud Gate and the Chicago Theatre) or an evening route. Both include a free 2-hour bike or kayak rental to use within three days of your tour.

Step-by-step itinerary

Stops and time at each

1. Wrigley Building5m
2. Palmer House Hilton10m · entry included
3. Chicago Theatre10m
4. Cloud Gate10m
5. Chicago Pedwaypass by

Chicago Food and Landmark Walking Tour

• Meet guide at starting point
• Taste deep-dish pizza
• Visit Wrigley Building
• Walk along Magnificent Mile
• See Chicago Theatre
• Stop at Palmer House for brownie
• Visit Millennium Park and Cloud Gate
• See Crown Fountain
• Pass Jay Pritzker Pavilion
• Taste Chicago-style hot dog
• Eat Italian Beef sandwich
• Try Garrett’s Chicago Mix popcorn
• Pass Chicago Loop landmarks
• See Historic Water Tower
• Visit Holy Name Cathedral

The experience

The tour starts with deep-dish pizza at a rotating roster of Chicago institutions: Lou Malnati's, Gino's East, Pizzeria Uno or Giordano's depending on your departure time and date. A slice arrives hot and thick, the crust stuffed and the cheese layered deep enough that you're eating with a fork. From there, the guide walks you through the Loop and along Michigan Avenue, stopping at an authentic hot dog stand for the Chicago version: all-beef frank on a poppy seed bun, yellow mustard, neon green relish, onions, tomato, pickle spear, sport peppers and celery salt. Ketchup is not part of the equation. The Italian beef comes next: thin-sliced, slow-roasted beef piled on fresh Italian bread and dunked in herb-infused au jus, with your choice of spicy giardiniera or sweet peppers.

Between bites, you're walking past the Wrigley Building's white terra cotta façade, the Chicago Theatre's dazzling marquee, and the Riverwalk. On daytime tours, the route includes Millennium Park and its landmarks: Cloud Gate (the Bean), Crown Fountain with its interactive water jets, and the Jay Pritzker Pavilion's Frank Gehry steel curves. You'll also taste Garrett's famous Chicago Mix popcorn (the sweet-and-salty blend that's been a local obsession since it arrived), and on morning departures, the original brownie from the Palmer House, a fudgy square with apricot glaze and walnuts that was created for the 1893 World's Fair and is still baked to the same recipe. Evening tours follow a different route and include a different dessert. The pace is relaxed: just 1.25 miles over three hours, with the guide rotating between the above-ground Loop and the Pedway (the underground tunnel network) depending on the season and weather.

Your guide is a local who knows the stories behind each stop: the grit and labor that built these foods, the history of the buildings you're passing, why the Water Tower survived the Great Chicago Fire when almost nothing else did. Groups stay small, and you get insider tips on other things to do around the city. As a bonus, every ticket includes a free 2-hour bike rental (year-round at Bobby's Bike Hike on Lake Shore Drive) or kayak rental (mid-May through mid-October at Ohio Street Beach), valid within three days before or after your tour date. You can add a craft beer upgrade ($19.99 for three 9oz pours) when you arrive.

What’s included

• Five Chicago food tastings: a slice of deep-dish pizza, a full Chicago-style hot dog with mustard, relish, onions, pickle and peppers, an Italian beef sandwich sample with au jus and peppers, Garrett's Chicago Mix popcorn, and a dessert (the original Palmer House brownie on daytime tours, a different treat on evening tours).
• a local English-speaking guide who shares Chicago's food history and architectural stories.
• insider tips on attractions and dining around the city.
• a free 2-hour bike rental or kayak rental valid within three days of your tour.

Options for this experience

2 options

Daytime food tourGuide in English · 11:00 and 11:30Lasts 3 hours, includes a full lunch. Meeting point: Plaza of the Americas, 430 N Michigan Ave, Chicago, IL 60611, USA

Nighttime food tourGuide in English · 17:30Lasts 3 hours, includes a full dinner. Meeting point: Gino's East, 162 E Superior St, Chicago, IL 60611, USA

You see the exact price of each option when you check availability.See dates & prices

Before you book

Days and timesEvery dayDepartures at 11:00, 11:30 and 17:30

Book up to2h before

AgesAdult (12 and older) · Youth (4 to 11 years) · Infant (under 4)

GroupUp to 16

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends at a different place from where it starts.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated yesterday

Good to know

Easy physical levelWheelchair accessibleAccessible transportStroller friendlyPublic transport nearby

Operated by Bobby's Bike, Hike & Food Tours - Chicago

Is this one for you?Book the daytime tour if you want to see Millennium Park, Cloud Gate and the Chicago Theatre while tasting the original brownie. The evening departure works better if you prefer a later start and a different route through the city's historic core.

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Top questions

Can children come?

Yes. Ticket types: Youth (4 to 11 years); Infant (under 4).

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

What's the difference between the day tour and the night tour?

The daytime tours depart at 11am, 11:30am or noon and include Millennium Park, Cloud Gate, the Chicago Theatre, and the original Palmer House brownie. The 5:30pm evening tour starts at Gino's East and takes a different route through the city, with a different dessert stop. Both include the same five food tastings and cost the same.

Can you accommodate dietary restrictions?

The tour operator can work with vegetarians and those who don't eat beef or pork. Let them know in the special requirements section when you book and email after booking to confirm. Gluten-free and vegan options are extremely limited, so those diets are difficult to accommodate.

What exactly is a Chicago-style hot dog?

A Chicago hot dog starts with an all-beef frank on a poppy seed bun, then gets yellow mustard, neon green relish, chopped onions, tomato wedges, a dill pickle spear, sport peppers for heat, and celery salt. Ketchup is not used. It's considered a violation of the tradition.

Is the tour wheelchair accessible?

Yes. The tour is wheelchair accessible, all surfaces and areas are accessible, and public transportation options are available nearby. The pace is relaxed at just 1.25 miles over three hours, and the guide can route you through the Pedway (underground tunnels) on colder days if that's easier.

How does the free bike or kayak rental work?

Every ticket includes a free 2-hour rental valid within three days before or after your tour date. Bike rentals are year-round at Bobby's Bike Hike on Lake Shore Drive and let you explore the 20-mile Lakefront Bike Trail. Kayak rentals run mid-May through mid-October at Ohio Street Beach on Lake Michigan. Saturday rentals are excluded during summer weekends (Memorial Day through Labor Day).

What if I want to add a drink to the tour?

A craft beer upgrade with three 9oz pours is available for $19.99 per person, ages 21 and up. You can purchase this when you arrive at the tour.