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

The Chicago Theatre

10 min

We start our tour under the dazzling marquee of the Chicago Theater (you might recognize from dozens of movies and TV shows) before heading off into the bustling city.

Chicago Pedway

20 min

Weather permitting, we'll head towards the Chicago Pedway. This unique feature of Chicago is used by locals and commuters daily to move about the city in a network of underground tunnels — especially necessary during the Midwest winters

City of Chicago - City Hall

20 min

We will pass by the City Hall-County Building, commonly known as City Hall. that houses the seats of government of the City of Chicago and Cook Count

The Picasso

10 min

Next, we will stop at the Chicago Picasso sculpture by Pablo Picasso in Daley Plaza . The 1967 installation of The Picasso, "precipitated an aesthetic shift in civic and urban planning, broadening the idea of public art beyond the commemorative."

Chicago River

20 min

You’ll enjoy feeling like a local as you zip past buildings and catch even more awesome views. If your guide takes you on a water taxi, you’ll be seeing the Chicago skyline from a totally different perspective, as well as sharing in the daily commute of local Chicagoans late for work.

Chicago Riverwalk

20 min

An award-winning $150 million, 1.25-mile promenade along the south bank of the Chicago River downtown. Weather permitting, we’ll take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Wrigley Building, and the Chicago Tribune.

Wrigley Building

20 min

We will pass the Wrigley Building, that it is located on the Magnificent Mile directly across Michigan Avenue from the Tribune Tower. Its two towers in an elaborate style were built between 1920 and 1924 to house the corporate headquarters of the Wrigley Company.

Tribune Tower

20 min

We'll pass by Tribune Tower, a 463-foot-tall (141 m), 36-floor neo-Gothic skyscraper located at 435 North Michigan Avenue.

The Magnificent Mile

20 min

We will pass by the Magnificent Mile - a premier commercial district in downtown. It was part of the 1909 Burnham Plan of Chicago, a visionary project to transform the city's urban landscape and it was built in the 1920s to replace an industrial and residential area. Here you find many shops, restaurants, hotels, and attractions. It is located on North Michigan Avenue.

Chicago Cultural Center

15 min

Step inside a Chicago Landmark building operated by Chicago's Department of Cultural Affairs. The Cultural Center houses the city's official reception venue, where the Mayor of Chicago has welcomed presidents, royalty, diplomats, and community leaders

Millennium Park

20 min

Next is picturesque Millennium Park, home to the iconic Bean sculpture. Here or nearby, your guide will conclude your tour and point you in the right direction toward more amazing sights, great lunch spots, or a drink recommendation.

Cloud Gate

20 min

We will pass by the Cloud Gate, a public sculpture by Indian-born British artist Anish Kapoor, that is the centerpiece of AT&T Plaza at Millennium Park in the Loop community area of Chicago.

River North

1 hour 30 min

Your food tour starts with a very well-known Chicago fare: the Chicago-style hot dog. Every Chicagoan has his or her own preference as to how the dog should be made, and you’ll get a chance to try your guides’ favorite version.
Next up is the world-famous Chicago deep-dish pizza! An entire meal unto itself, this staple of the Chicago food scene originated in River North in the 1940s, when workers and families needed filling dishes at low prices. Your guide will take you to a pizza place that’s an icon to Chicago natives to try the real deal for yourself.
After you’ve filled up on pizza and hot dogs, you’ll take a stroll through two more establishments, each one essential to Chicago’s food culture. We’ll then continue our tasting journey with a classic Chicago sandwich: Italian beef. You’ll sample this sandwich in a real Chicago institution — no-frills decor included!

Historic Water Tower

1 hour 30 min

We will pass by the beautiful water tower that was constructed to house a large water pump, intended to draw water from Lake Michigan. Built in 1869, it is the second-oldest water tower in the United States.

The Loop

1 hour 30 min

Stroll through the main streets near the Loop Chicago which offers a wonderful concentration of museums, restaurants, bars and historic landmarks uniquely mixed with modern architecture, shops and art galleries.