Tour the streets of Chicago to see the beauty and legacy left behind by the Prohibition Era. See the amazing architecture, iconic sights (both old and new), the city's best spots along the way as you explore on foot.
We begin at the iconic Chicago Theater marquee, then explore the city.
Weather permitting, we’ll explore the Chicago Pedway, a network of underground tunnels used by locals and commuters.
We'll pass the City Hall-County Building, home to Chicago’s government and Cook County offices.
Next, we’ll stop at the Chicago Picasso in Daley Plaza, a 1967 installation that transformed public art and urban planning.
Feel like a local as you walk past iconic buildings, catch stunning skyline views, and share in the daily commute along Chicago’s main artery.
Weather permitting, we’ll stroll the award-winning Chicago Riverwalk, enjoying views of iconic buildings like Marina Towers, the Wrigley Building, and the Tribune Tower.
We’ll pass the iconic Wrigley Building at 400 N Michigan Ave, a historic landmark in the heart of Chicago.
Next, we’ll pass by Tribune Tower, a 463-foot, 36-story neo-Gothic skyscraper at 435 North Michigan Avenue.
Next, we’ll pass the Magnificent Mile on North Michigan Avenue, a vibrant district of shops, restaurants, and attractions, created as part of the 1909 Burnham Plan.
Step inside a Chicago Landmark, the Cultural Center, where the Mayor has welcomed presidents, royalty, and dignitaries
Next is the picturesque Millennium Park, home to the iconic Bean sculpture. Your guide will end the tour here, offering tips on nearby sights, lunch spots, or drinks.
We’ll end the tour at the Cloud Gate sculpture, also known as 'The Bean,' the centerpiece of Millennium Park.
The Chicago Theatre (underneath the marquee), 175 N. State Street, Chicago, IL 60601
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.
Dietary Notes
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.
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.
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.
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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.
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'.
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.
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.
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 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.
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.
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.
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.
A sweet and savory snack made with caramel and cheese-flavored popcorn, often sold in colorful boxes at street corners and ballgames.
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.
United States Dollar (USD)
Central Time Zone (CT) (GMT-6)
120VV, 60HzHz
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.
Union Station, Ogilvie Transportation Center
Greyhound Station, Megabus Terminal
The 'L' is a convenient and affordable way to get around Chicago. It consists of eight color-coded lines.
Available • Apps: Uber, Lyft
Car, Bike, Scooter
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 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.
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.
Price varies by option