Chicago Introduction Walking Tour, Chicago

Chicago Introduction Walking Tour (Self Guided), Chicago

Sitting on the shore of Lake Michigan in Illinois, Chicago is the third most populous metropolis in the United States, whereas when incorporated on August 12, 1833, the town had a population of only about 200 people. The first non-indigenous permanent settler in Chicago was explorer of African and French descent, Jean Baptiste Point du Sable, who arrived here in the 1780s and is commonly regarded as the "Founder of Chicago".

The first known reference to the site of the city as "Chicagou" dates back to 1679. It stems from a French rendering of the indigenous Miami-Illinois word “shikaakwa” which means wild garlic or onion, more commonly known as "ramps". It was reportedly due to the large quantity of this spice growing in the area. Throughout its history, Chicago has had many different nicknames, including the Windy City, Chi-Town, Second City, and the City of the Big Shoulders, referring to its numerous towers and high-rises.

Famed for its bold architecture, Chicago has a skyline punctuated by skyscrapers, such as the iconic John Hancock Center and Willis Tower (formerly the Sears Tower), to mention but a few. A thriving hub of international trade and commerce, the city also abounds in vibrant tourist attractions. Among these are renowned museums, such as the Art Institute of Chicago with its noted Impressionist and Post-Impressionist works, as well as lake front parks and a huge variety of restaurants and shops.

To get a sense of today's Chicago and to explore some of its top attractions, take this self-guided walk!
How it works: Download the app "GPSmyCity: Walks in 1K+ Cities" from iTunes App Store or Google Play to your mobile phone or tablet. The app turns your mobile device into a personal tour guide and its built-in GPS navigation functions guide you from one tour stop to next. The app works offline, so no data plan is needed when traveling abroad.

Download The GPSmyCity App

Download 'GPSmyCity: Walks in 1K+ Cities' app for IOS   Download 'GPSmyCity: Walks in 1K+ Cities' app for Android

Chicago Introduction Walking Tour Map

Guide Name: Chicago Introduction Walking Tour
Guide Location: USA » Chicago (See other walking tours in Chicago)
Guide Type: Self-guided Walking Tour (Sightseeing)
# of Attractions: 11
Tour Duration: 2 Hour(s)
Travel Distance: 3.6 Km or 2.2 Miles
Author: doris
Sight(s) Featured in This Guide:
  • Willis Tower / Skydeck Chicago
  • Rookery Building
  • Art Institute of Chicago
  • Crown Fountain
  • Cloud Gate
  • Millennium Park
  • Michigan Avenue Bridge
  • Wrigley Building
  • Michigan Avenue, “The Magnificent Mile”
  • Water Tower
  • Water Tower Place
Willis Tower / Skydeck Chicago

1) Willis Tower / Skydeck Chicago (must see)

Commonly referred to as the Sears Tower, Chicago's Willis Tower stands 108 stories high and for almost 25 years remained the world's tallest building having surpassed, upon its completion in 1973, the World Trade Center twin towers in New York. It also remained the tallest building in the Western Hemisphere up until 2014 when a new building at the reconstructed World Trade Center site was completed. Currently, the Willis Tower is the second-tallest building in the United States and the Western hemisphere, and the 16th-tallest in the world.

The Willis Tower observation deck, called the Skydeck, opened on June 22, 1974. Located on the 103rd floor at an elevation of 1,353 feet (412.4 m), it is the highest observation deck in the United States and one of Chicago's most famous tourist attractions. On a windy day, visitors can feel the building sway and, on a clear day, see far over the plains of Illinois and across Lake Michigan to Indiana, Michigan, and Wisconsin. Elevators take about 60 seconds to reach the top during which passengers are able to feel the pressure change as they move upward.

Why You Should Visit:
The views are genuinely stunning and, providing you have the stomach for it, you should definitely line up to step onto the Ledge – the glass box that juts out the side of the viewing floor – perfect for photo ops.

The observatory is not very big but waiting for the actual glass bottom ledge takes a while, so try going straight to the ledge first to beat the crowd and then take your time to go around.

Opening Hours:
Daily: 10am-8pm
Sight description based on Wikipedia.
Rookery Building

2) Rookery Building

The Rookery Building is a historic landmark located in the Loop community area of Chicago. Completed by John Wellborn Root and Daniel Burnham in 1888, it is considered one of their architectural masterpieces. The oldest standing high-rise in Chicago, the building is twelve stories tall and measures 181 feet (55 m). The Rookery has a unique style with exterior load-bearing walls and an interior steel frame. The name Rookery comes from the previous building on this site, which became home to many birds, especially pigeons. The red marble, terracotta and brick facade is a combination of Roman Revival and Queen Anne styles that embraced Richardsonian Romanesque architecture. The building itself is a combination of iron framing and masonry bearing walls and, as such, manifested a transition from masonry to steel skeleton load-bearing structures.

Why You Should Visit:
From the outside, it looks like an ordinary classic building of Chicago, whereas, on the inside, it really gets you pulled in and held in awe.

You can stop in and see the lobby for free, but to see the best parts (such as the famed D-spiral staircase & other architectural aspects) you will need a guided tour which is offered Monday through Friday at noon.

Opening Hours:
Mon-Fri: 8am-6pm; Sat: 8am-2pm
Sight description based on Wikipedia.
Art Institute of Chicago

3) Art Institute of Chicago (must see)

The Art Institute of Chicago (AIC) is an encyclopedic fine art museum boasting one of the world's grandest collections of Impressionist and Post-Impressionist art in its permanent collection. The diverse holdings of the museum also include significant Old Master works, American art, European and American decorative arts, Asian art, as well as modern and contemporary art. The AIC is located in Chicago's Grant Park at 111 South Michigan Avenue within the Landmark Historic Michigan Boulevard District. At one million square feet, this is the second largest art museum in the United States behind only the Metropolitan Museum of Art in New York.

Why You Should Visit:
A world-class collection with much depth and variety of artworks, artifacts, antiquities and curiosities catering for all tastes and ages. The museum is thoughtfully laid out and you can take a guided tour starting at noon.

If you're not a member, go during the week to avoid crowds if you can.
Prioritize what you want to see! Buy the little booklet that is sold with the tickets; it will help you with the selection and makes for a nice memorabilia.
There are several restaurants inside, so pace yourself with lunch, coffee and/or drinks. The cafe in the basement is one of the nicest museum cafes in Chicago, with a wide array of grill & healthy fare.

Opening Hours:
Fri-Wed: 10:30am–5pm; Thu: 10:30am-8pm
Sight description based on Wikipedia.
Crown Fountain

4) Crown Fountain

Crown Fountain is an interactive work of public art and video sculpture featured in Chicago's Millennium Park, which is located in the Loop community area. Designed by Catalan artist Jaume Plensa, it opened in July 2004. The fountain is composed of a black granite reflecting pool placed between a pair of glass brick towers. The towers are 50 feet (15.2m) tall and use light-emitting diodes (LEDs) to display digital videos on their inward faces. Weather permitting, the water operates from May to October, intermittently cascading down the two towers and spouting through a nozzle on each tower's front face. Residents and critics have praised the fountain for its artistic and entertainment features. It highlights Plensa's themes of dualism, light, and water, extending the use of video technology from his prior works. The use of water is unique among Chicago's many fountains, in that it promotes physical interaction between the public and the water.

Why You Should Visit:
A very nice addition to Chicago's world-renowned public art collection; fun to sit down and relax (or else bring a towel and spare clothes!).
The fountain & water jets are great for the kids to run around and frolic through, especially on a hot summer day.

The lighting is fantastic – you should go at night to see the full effect.
Sight description based on Wikipedia.
Cloud Gate

5) Cloud Gate (must see)

Cloud Gate is a public sculpture, centerpiece of AT&T Plaza at Millennium Park, constructed between 2004 and 2006. Made entirely of stainless steel – 168 plates welded together and polished to conceal the seams – the sculpture stands three stories high, measuring 66 feet long, 33 feet high and 42 feet wide, and weighting 100 tons. It has been lovingly dubbed by the locals as "The Bean," although the design is said to have been inspired by a drop of mercury. Concave at the bottom, it creates a spectacular fun mirror effect for those walking underneath, reflecting distorted images of the Chicago skyline.

At the time, prior to its installation, the sculpture was subject to a controversy among experts, some of whom believed it could not be implemented because of the technological difficulties associated with its construction, assembly, upkeep and maintenance. Although a feasible solution was eventually found, the project fell behind schedule and was still unfinished by the time Millennium Park was opened in 2004. Cloud Gate was completed and formally dedicated only on May 15, 2006, and has since enjoyed great acclaim, both at home and abroad.

Why You Should Visit:
Fascinating piece of artwork that allows to playfully take pictures at different angles and with amazing backgrounds.

Visit on a sunny day for better photos. Note that on a rainy day if there's a thunderstorm, you won't even be allowed near the sculpture as it poses a risk of electrocution!
Millennium Park

6) Millennium Park (must see)

Millennium Park is a public park in the Loop community area of Chicago. Originally, it was intended to celebrate the third millennium; hence the name. Bounded by Michigan Avenue, Randolph Street, Columbus Drive, and East Monroe Drive, this is a prominent civic center near the city's Lake Michigan shoreline that covers a 24.5-acre (99,000 m2) section of northwestern Grant Park. The latter is linked to Millennium Park by the BP Pedestrian Bridge and the Nichols Bridgeway.

The park features a variety of public art and, in 2015, became the location of the city's annual Christmas tree lighting. The park is free to enter and is a home to multiple attractions such as the Jay Pritzker Pavilion, Cloud Gate, the Crown Fountain, the Lurie Garden and others. Because it sits atop a parking garage and the commuter rail Millennium Station, the park is considered the world's largest rooftop garden, and has received awards for its accessibility and green design.

In 2017, Millennium Park was the top tourist destination in Chicago and the American Midwest, and was placed among the top ten in the United States with 25 million annual visitors.

Why You Should Visit:
Enjoyable for all age groups. Great for singles, couples, groups, family.
With so many sites and attractions, you can spend days just walking and exploring.

If you get up early in the morning, you'll have the park to yourself and be able to enjoy interacting with the exhibits more personally.
Go back later in the evening as both the exhibits and atmosphere change.

Opening Hours:
Daily: 6am-11pm
Sight description based on Wikipedia.
Michigan Avenue Bridge

7) Michigan Avenue Bridge

The Michigan Avenue Bridge (officially known as DuSable Bridge) is a bascule bridge that carries Michigan Avenue across the Chicago River, the boundary between the Loop and Near North Side community areas, in downtown Chicago. The bridge was built from 1917–1920 as two parallel bridges that operate independently of one another. It was designed by architect Edward H. Bennett, and is an early example of a fixed trunnion bascule bridge, which later became widely known as a "Chicago style bascule". The bridge features friezes including Wheeler Williams' "Tablets to Pioneers". When the bridge was completed it was the main link between the north side and downtown. In spring and autumn, it is raised twice a week to allow sailboats to pass between Lake Michigan and inland boat yards where they are stored for winter. The plaza is home to Cloud Gate, a three-story, 110-ton steel sculpture that has been dubbed by residents as "The Bean".

Why You Should Visit:
The best place to see the Chicago River in all its glory, and great for pictures overlooking Magnificent Mile. You can also catch a ride on the water taxi!

This bridge makes it possible to cross the river without getting your feet wet!
There is a statue of Mr. DuSable on its northern side, great for a selfie that nobody will understand
Sight description based on Wikipedia.
Wrigley Building

8) Wrigley Building

The Wrigley Building is a skyscraper located directly across Michigan Avenue from the Tribune Tower on the Magnificent Mile. It was built to house the corporate headquarters of the Wrigley Company. The building was modeled on the Giralda tower of Seville's Cathedral combined with French Renaissance details. The 425-foot (130 m) south tower was completed in April 1921 and the north tower in May 1924. Walkways between the towers were added at the ground level and the third floor. At night, the building is brightly lit with floodlights.

The Wrigley Building was Chicago’s first air-conditioned office building. If one walks through the center doors, they will find themselves in a secluded park area overlooking the Chicago River.

The new owners made the building more attractive to businesses by adding a Walgreens, a coffee shop, a fitness center and a nursing room for mothers.

Why You Should Visit:
One of the most beautiful buildings in Chicago, amazing from all angles and at all times of day, easy to get to, and surrounded by other cool architecture – a must-see in the downtown area.

Tours of the building are available inside.

Opening Hours:
Mon-Fri: 8am-6pm; Sat: 8am-12pm
Sight description based on Wikipedia.
Michigan Avenue, “The Magnificent Mile”

9) Michigan Avenue, “The Magnificent Mile” (must see)

Michigan Avenue, and particularly the upscale section thereof between the Chicago River and Oak Street in the Near North Side, known as “The Magnificent Mile”, is currently Chicago's largest shopping destination.

As a premier commercial district – home to an array of mid-range and high-end shops, restaurants and hotels, – the street caters primarily to tourists and the affluent. Many of the world's leading retail stores populate the avenue, including luxury department stores Bloomingdale's, Neiman Marcus, Saks Fifth Avenue, and Nordstrom. It is also home to three urban shopping centers: Water Tower Place, The Shops at North Bridge, and 900 North Michigan Shops.

Renowned and critically acclaimed restaurants, located along The Mag Mile, provide a variety of dining options. However, if you come to Chicago specifically for the famous local pizza, then should check out some of these locations: Gino's East – offering some of the best deep dish pizza experience in Chicago for half a century; and Lou Malnati's – the home of the BEST Chicago-style deep dish pizza in the world!
Water Tower

10) Water Tower

Built in 1869, the Water Tower is one of the few structures that survived the Great Chicago Fire of 1871 and, as such, represents a monument to that event. With its smaller Gothic-style towers, the building looks more like a tiny European 13th-century castle. The Water Tower is inviting to make a stop at the Visitors' Center and the onsite City Gallery running free art exhibitions for the public.

Why You Should Visit:
Great photo ops here and there's a nice little green space with benches around it to rest.

While it looks good during the day, it looks even better at night when it's all lit up.

Opening Hours:
Mon-Sat: 10am-9pm; Sun: 10am-6pm
Water Tower Place

11) Water Tower Place

Water Tower Place claims to be Chicago's premier shopping destination. This 758,000 sq ft mall features eight sophisticated levels with more than 100 stores and restaurants, plus a mixture of distinctive specialty boutiques. At the entrance, visitors are greeted with a beautiful water display and an equally beautiful glass elevator.

Water Tower Place is ideal for grabbing a bite. Food Life, an urban food court within the mall featuring 14 distinct kitchens, offers a wealth of quality international fare for breakfast, lunch or dinner made from scratch every day to dine in or to go – fresh and fast choices all in a single location. Menus include American comfort-food, Mexican, Italian and Asian dishes. From Chicken Tacos and BBQ Brisket to Deep Dish Pizza and Fried Chicken, the whole family will find something to enjoy here.

At the Mezzanine level there's a nice, less busy alternative to Foodlife, called Foodease, serving favorite dishes from iconic Chicago restaurants. The menu includes made-to-order sandwiches and sushi, full hot-, cold- and soup bars, as well as in-house bakery items. The wine bar and retail wine shop offers more than 200 selections of red, white, rosé and sparkling wines.

Great vibe for hanging out with family and friends – a unique, high-energy urban shopping experience!

Operation hours: Monday-Saturday: 10:00 am - 9:00 pm; Sunday: 11:00 am - 6:00 pm

Walking Tours in Chicago, Illinois

Create Your Own Walk in Chicago

Create Your Own Walk in Chicago

Creating your own self-guided walk in Chicago is easy and fun. Choose the city attractions that you want to see and a walk route map will be created just for you. You can even set your hotel as the start point of the walk.
Millennium and Grant Parks Walking Tour

Millennium and Grant Parks Walking Tour

The city of Chicago is renowned for its outdoor green spaces. One such “forever free and open” space, is called Grant Park and was established in 1844. In fact, upon foundation, it was called Lake Park, but was renamed in 1901 after the American Civil War General and United States President, Ulysses S. Grant.

Popularly referred to as “Chicago's front lawn,” this lakefront park is...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 2.7 Km or 1.7 Miles
University of Chicago Walking Tour

University of Chicago Walking Tour

Founded in 1890, the University of Chicago is among the world’s most prestigious educational institutions. As of 2020, the University’s students, faculty and staff have included 100 Nobel laureates, giving it the fourth-most affiliated Nobel laureates of any university.

Set in the heart of Chicago’s famous eclectic neighborhood, Hyde Park, the campus is worth a visit as it offers a...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 2.5 Km or 1.6 Miles
Loop District Architecture Walking Tour

Loop District Architecture Walking Tour

Chicago features an outstanding architectural legacy, having long been connected with some of architecture's most important names: Frank Lloyd Wright, Louis Sullivan, Mies van der Rohe, Holabird & Root, and others. The multi-layered Loop District, in particular, offers an extensive number of Chicago’s famous architectural “must-sees” – from modern skyscrapers to historic buildings...  view more

Tour Duration: 3 Hour(s)
Travel Distance: 4.6 Km or 2.9 Miles
Chicago Old Town Walking Tour

Chicago Old Town Walking Tour

Settled in 1850 by German immigrants, Chicago’s Old Town neighborhood is a popular destination for locals and visitors who cater to the entertainment venues, restaurants, pubs, coffee shops and boutiques – all of which have turned an area once referred to as the “Cabbage Patch” into an attraction that rivals Navy Pier, Wrigley Field and the Magnificent Mile.

Start your Old Town walking...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 2.6 Km or 1.6 Miles
Chicago Chinatown Walking Tour

Chicago Chinatown Walking Tour

Tucked away just south of the Loop, the Chinatown of Chicago was established in 1912 and is considered one of the best examples of American Chinatown. While it may be one of Chicago’s smallest neighborhoods geographically, it is big on character, colors, sights, sounds, and flavors. Here, you’ll find a wide range of unique boutiques, specialty shops, religious sights, authentic Chinese...  view more

Tour Duration: 1 Hour(s)
Travel Distance: 1.7 Km or 1.1 Miles
Chicago Navy Pier Walking Tour

Chicago Navy Pier Walking Tour

Additional to scenic views of the lake, the boats, and the city skyline, the Navy Pier offers a variety of attractions on the waterfront – for kids as well as adults – that draw nearly ten million people annually, making this Chicago's most visited spot. Yes, some may see it as a “tourist trap”, but it is worth the time and money to spend some time here, so take this self-guided walk...  view more

Tour Duration: 1 Hour(s)
Travel Distance: 1.0 Km or 0.6 Miles

Useful Travel Guides for Planning Your Trip

Chicago Souvenirs: 15 Distinct Local Products to Bring Home

Chicago Souvenirs: 15 Distinct Local Products to Bring Home

One of the most fascinating cities in the U.S., if not the whole world, Chicago has no shortage of things closely associated with it, often due to their direct origin (blues, gangstership, etc.), so one might literally be spoiled for choice as to what to choose as a "piece" of Chicago to...