Chicago in a Day: Food, History & Architecture Walking Tour

Chicago , United States

Chicago in a Day: Food, History & Architecture Walking Tour

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About this experience

Immerse yourself in Chicago's rich history and vibrant culinary scene on this captivating walking tour. Discover the city's iconic architecture and Prohibition-era charm while indulging in delectable local cuisine. From deep-dish pizza to hidden gems, savor the flavors of Chicago as a knowledgeable guide unveils the city's culinary secrets and fascinating history.

Available options

Private Chicago in Day

Small Group Chicago in a Day

What's included

Hear stories of Chicago’s past — from Prohibition to the Great Fire and immigrant history

Explore top sights & hidden gems — Riverwalk, Magnificent Mile, Pedway, Wrigley Building

Taste Chicago's iconic eats — deep-dish pizza, hot dog, Italian beef & more included

Led by expert local guides — passionate storytelling from true Chicago insiders

Enjoy a personal, relaxed, and interactive experience - Small group size (max 12)

Travel for good — run by a certified B Corp committed to ethical, responsible tourism

Visit Millennium Park & The Bean — snap pics at Chicago’s most famous modern landmark

Detailed itinerary

Stop 1

We begin under the dazzling Chicago Theater marquee, famous from movies, before diving into the lively streets of the city.

Stop 2

Weather permitting, we'll explore the Chicago Pedway, a network of underground tunnels used daily by locals and commuters, especially in winter.

We’ll pass the City Hall-County Building, home to the City of Chicago and Cook County governments.

Stop 4

Feel like a local as you walk past iconic buildings, enjoy stunning skyline views, and share in the daily commute along Chicago’s main artery.

Stop 5 Pass by

Next, we’ll pass the Wrigley Building on the Magnificent Mile, built between 1920 and 1924 to house the Wrigley Company's headquarters.

Stop 6 Pass by

Then, we’ll pass the Tribune Tower, a 463-foot, 36-story neo-Gothic skyscraper at 435 North Michigan Avenue.

Stop 7 Pass by

Next, we’ll visit picturesque Millennium Park, home to the iconic Bean sculpture. Your guide will then offer recommendations for more sights, lunch spots, or drinks.

Stop 8 Pass by

We'll pass the Cloud Gate sculpture, also known as 'The Bean,' the centerpiece of Millennium Park.

Stop 9 Pass by

At the end, stroll through the main streets near the Loop, where museums, restaurants, bars, historic landmarks, and modern architecture blend together.

What's not included

Gratuity

Drinks and additional food

Available languages

Guide guide

Reviews breakdown

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583 reviews

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Tripadvisor 5.0

557 reviews

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Important information

Wheelchair accessible

Infants and small children can ride in a pram or stroller

Service animals allowed

Public transportation options are available nearby

Transportation options are wheelchair accessible

Suitable for all physical fitness levels

This is a child-friendly walking tour. Children under the age of 6 are permitted to join this tour free of charge.

Please note: food options and portion sizes will vary depending on the season and where we stop that day but the total amount of food included will be equal to a full meal.

Suitable for all ages and fitness levels, but please note that this tour covers between 4.8 to 6.4 km (3-4 miles) of walking.

We can accommodate vegetarian options but cannot accommodate other food allergies or dietary preferences. Please notify us in advance if you have any dietary requests.

Experiences happen rain, shine, or snow. Please dress accordingly.

Meeting point

The Chicago Theatre (underneath the marquee), 175 N. State Street, Chicago, IL 60601

Important notes

Additional Information
In the event of a site closure, we will do our best to replace it with a similar alternative.
This tour runs year-round and will proceed rain or shine unless such weather constitutes a dangerous situation.

Child Policy
Please inform us if you’ll be bringing a child under the age of 6.

Dress Standards
Comfortable shoes for walking are recommended.

Food Inclusions
Please note: food options and portion sizes will vary depending on the season and where we stop that day but the total amount of food included will be equal to a full meal.

Tipping Your Guide
A tip / gratuity for your guide is not included in the price of this tour. If you feel that your guide has done their best to provide a personal and engaging experience, giving a gratuity is encouraged.

Review us
How did we do? Your experience matters! Let us know by leaving a review.

About Chicago

Chicago is a vibrant city known for its stunning architecture, rich cultural heritage, and world-class cuisine. Situated along the shores of Lake Michigan, it offers a unique blend of urban excitement and natural beauty, making it a must-visit destination for travelers from around the globe.

Top Attractions

Millennium Park

Millennium Park is a famous public park in downtown Chicago, known for its modern art and architecture. It's home to the iconic Cloud Gate sculpture, also known as 'The Bean'.

Park 1-2 hours Free

Art Institute of Chicago

One of the oldest and largest art museums in the United States, the Art Institute of Chicago houses an impressive collection of artworks from around the world.

Museum 2-3 hours $25 (adults), Free for children under 14

Skydeck Chicago

Located on the 103rd floor of the Willis Tower, Skydeck Chicago offers breathtaking views of the city and Lake Michigan. Visitors can step out onto The Ledge, a glass balcony extending out from the building.

Observation Deck 1-2 hours $28 (adults), $20 (children 3-11)

Navy Pier

Navy Pier is a 3,300-foot-long pier on the Chicago shoreline of Lake Michigan. It offers a variety of attractions, including shops, restaurants, and rides.

Entertainment 2-4 hours Free to enter, individual attractions have varying costs

Wrigley Field

Wrigley Field is a historic baseball park located on the North Side of Chicago. It's home to the Chicago Cubs and offers a unique atmosphere for sports fans.

Sports 2-4 hours (game duration varies) Ticket prices vary depending on the game and seating

Must-Try Local Dishes

Deep-Dish Pizza

A thick, buttery crust filled with layers of cheese, toppings, and tomato sauce. It's a Chicago classic and a must-try for pizza lovers.

Dinner Contains gluten and dairy. Vegetarian and vegan options are available at some restaurants.

Chicago-Style Hot Dog

A steamed or grilled all-beef hot dog topped with yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato wedges, pickled sport peppers, and a dash of celery salt, all served on a poppy seed bun.

Snack Contains gluten and dairy. Vegetarian and vegan options are available at some hot dog stands.

Italian Beef Sandwich

Thinly sliced beef cooked in its own juices and served on an Italian roll. It's typically dipped in the juices and topped with sweet or hot peppers.

Lunch/Dinner Contains gluten and beef. Vegetarian and vegan options are available at some Italian beef restaurants.

Chicago-Style Popcorn

A sweet and savory snack made with caramel and cheese-flavored popcorn, often sold in colorful boxes at street corners and ballgames.

Snack Contains dairy. Vegetarian and vegan options are available at some popcorn stands.

Popular Activities

Kayaking on the Chicago River Biking along Lake Michigan Rock climbing at First Ascent Picnicking in Millennium Park Yoga in the park Spa treatments at The Peninsula Chicago Visiting the Art Institute of Chicago Attending a performance at the Chicago Symphony Orchestra

Best Time to Visit

May to September

This is the best time to visit Chicago for outdoor activities, festivals, and sightseeing. The weather is warm and pleasant, making it ideal for exploring the city's parks and attractions.

15°C to 30°C 59°F to 86°F

Practical Information

Language

Official: English
Widely spoken: Spanish, Polish, Chinese
English: Widely spoken

Currency

United States Dollar (USD)

Time Zone

Central Time Zone (CT) (GMT-6)

Electricity

120VV, 60HzHz

Safety Information

Overall Safety Rating: Generally safe

Chicago is generally safe for tourists, but visitors should be aware of their surroundings and take precautions to protect themselves and their belongings. Some areas of the city have higher crime rates, and visitors should research their destinations before traveling.

Important Precautions:

• Be aware of your surroundings and keep valuables secure
• Use licensed taxis or ride-sharing services
• Avoid walking alone in isolated or poorly lit areas, especially at night

Getting there

By air

O'Hare International Airport • 27 km (17 miles) from city center
Midway International Airport • 13 km (8 miles) from city center

By train

Union Station, Ogilvie Transportation Center

By bus

Greyhound Station, Megabus Terminal

Getting around

Public transport

The 'L' is a convenient and affordable way to get around Chicago. It consists of eight color-coded lines.

Taxis

Available • Apps: Uber, Lyft

Rentals

Car, Bike, Scooter

Neighborhoods

The Loop Lincoln Park Wicker Park Magnificent Mile Pilsen

Day trips

Navy Pier

2 km (1.2 miles) • Half day to full day

Navy Pier is a 3,300-foot-long pier on the Chicago shoreline of Lake Michigan. It offers a variety of attractions, including shops, restaurants, and rides.

Wrigley Field

10 km (6.2 miles) • Half day to full day

Wrigley Field is a historic baseball park located on the North Side of Chicago. It's home to the Chicago Cubs and offers a unique atmosphere for sports fans.

Museum Campus

3 km (1.9 miles) • Half day to full day

The Museum Campus is a 57-acre park located on the southern tip of Grant Park in Chicago. It's home to several world-class museums, including the Field Museum, the Shedd Aquarium, and the Adler Planetarium.

Festivals

Lollapalooza • Early August (4-day festival) Chicago Jazz Festival • Late August to early September (weekend festival) Chicago Food Festival • Early September (weekend festival)

Pro tips

Visit popular attractions early in the morning or late in the afternoon to avoid crowds and long wait times
Use the Ventra card for easy and convenient payments on public transportation
Explore the city's diverse neighborhoods and culinary scene to get a true sense of Chicago's character and culture
Take an architecture river cruise to see the city's stunning skyline and learn about its architectural history
Visit the city's many parks and outdoor spaces to enjoy nature and outdoor activities, even in the heart of the city