City Orientation Walk (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. In the course of the 18th century, the area of Chicago was successively inhabited by various Native American tribes who, following several victorious military campaigns of the United States against the Indians, were removed from their land. The first known 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", and 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 orientation walk!
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City Orientation Walk Map

Guide Name: City Orientation Walk
Guide Location: USA » Chicago (See other walking tours in Chicago)
Guide Type: Self-guided Walking Tour (Sightseeing)
# of Attractions: 18
Tour Duration: 4 hour(s)
Travel Distance: 6.1 Km or 3.8 Miles
Author: doris
1
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.

Tip:
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
2
Rookery Building

2) Rookery Building (must see)

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.

Tip:
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
3
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.

Tip:
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
4
Buckingham Fountain

4) Buckingham Fountain (must see)

Buckingham Fountain is a major landmark considered to be Chicago's front door due to its location in Grant Park, the city's front yard, at Columbus Drive and Congress Parkway. The fountain was dedicated in 1927 and was designed by Jacques Lambert. Its body of water represents Lake Michigan, whereas each seahorse therein symbolizes a state bordering the lake. The statues were created by the French sculptor Marcel F. Loyau. The design of the fountain was based on the Bassin de Latome and modeled after Latona Fountain at Versailles. The fountain runs from 8:00am to 11:00pm every day between mid-April and mid-October. During a 20-minute water display that runs every hour on the hour, the center jet shoots up to 150 feet (46 m) in the air. At dusk, a light and music show coincides with the water display. The last show of the night begins at 10:00pm.

Why You Should Visit:
Set against the Chicago city skyline in the background, this fountain forms quite a sight – one of the greatest photo op spots in the city.
Also, the water goes higher than just about any other fountain you've ever seen!

Tip:
Remember that the fountain is shut down for winter months.
Otherwise, enjoy the light show after dark!

Opening Hours:
Daily: 8am-11pm
Sight description based on wikipedia
5
Grant Park

5) Grant Park (must see)

Regarded as Chicago's “front yard”, Grant Park opened way back in 1835. The main attraction here is the Clarence Buckingham Fountain, situated in the center of the park. Its structure has a French style geometric design. The park is divided into different areas with flower gardens, trees and monuments. One distinct monument portrays the sixteenth president of the United States, Abraham Lincoln.

Why You Should Visit:
Perfect for a date, a solid stroll, a run, a bike ride, a family outing...
Plenty of places to grab a spot for a picnic and spend some quiet, relaxing time.
There are hundreds of events all summer long and plenty in the winter as well.

Tip:
Bring a towel/blanket to sit on for concerts and to take a break under a tree.
If you like biking, try the lakeside route – it's great!

Opening Hours:
Daily: 6am-11pm
6
BP Pedestrian Bridge

6) BP Pedestrian Bridge (must see)

The BP Pedestrian Bridge, or simply BP Bridge, is a girder footbridge in the Loop community area of Chicago. It spans Columbus Drive to connect Daley Bicentennial Plaza with Millennium Park, both parts of the larger Grant Park. Designed by Pritzker Prize-winning architect Frank Gehry, the bridge opened along with the rest of Millennium Park on July 16, 2004. Gehry had been courted by the city to design the bridge and the neighboring Jay Pritzker Pavilion, and eventually agreed to do so after the Pritzker family funded the Pavilion. BP Bridge is described as snakelike because of its curving form. Designed to bear a heavy load without structural problems caused by its own weight, the bridge has won awards for its use of sheet metal. Extensive sculptural use of stainless steel plates to express abstraction and biomorphic allusions have been representative of Gehry's style and earned the bridge much praise for its aesthetics.

Why You Should Visit:
On a beautiful day, this is one of the most picturesque walks you can take in Chicago!
The wide curvy path provides continuous opportunities to enjoy the city skyline and lake view, as well as the nice views of both Millennium Park and Maggie Daley Park.
Sight description based on wikipedia
7
Jay Pritzker Pavilion

7) Jay Pritzker Pavilion (must see)

Jay Pritzker Pavilion, also known as Pritzker Pavilion or Pritzker Music Pavilion, is a bandshell in Millennium Park in the Loop community area of Chicago. The pavilion was named after Jay Pritzker, whose family is known for owning Hyatt Hotels. The building was designed by architect Frank Gehry, who accepted the design commission in April 1999. Pritzker Pavilion serves as the centerpiece for Millennium Park and is the new home of the Grant Park Symphony Orchestra and Chorus plus the Grant Park Music Festival, the nation's only remaining free outdoor classical music series. It also hosts a wide range of music series and annual performing arts events. Performers ranging from mainstream rock bands to classical musicians and opera singers have appeared at the pavilion, which even hosts physical fitness activities such as yoga.

Why You Should Visit:
Great outdoor theater experience: interesting design, state of the art acoustics, ample seating (both seats & lawn), large stage with huge video screen and restrooms adjacent, convenient location.
Most concerts are free and well attended, and there is a wide variety of entertainment.

Tip:
Look up the presentation schedule and either get there early or buy seats. The park in front is also an option to enjoy the presentations, though you might not enjoy an absolutely clear sound.
Sight description based on wikipedia
8
Crown Fountain

8) Crown Fountain (must see)

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.

Tip:
The lighting is fantastic – you should go at night to see the full effect.
Sight description based on wikipedia
9
Cloud Gate

9) Cloud Gate (must see)

Made up of 168 stainless steel plates welded together, The Cloud Gate, also called simply "The Bean", weighs over 110 tons, and is 66 feet long and 33 feet high. This amazing sculpture has the appearance of a giant drop of liquid mercury; its surface features spectacular images of the Chicago skyline. Being very concave, the bottom of the sculpture creates a spectacular fun mirror effect of the people walking underneath it.

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

Tip:
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 statue as it poses a risk of electrocution!
10
Millennium Park

10) 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.

Tip:
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
11
State Street

11) State Street

State Street is located in the heart of Chicago. This historical venue is Chicago's most famous shopping destination. It offers a pleasing blend of affordable and stylish shopping. Macy's multi-level department store anchors the retail row which includes fashion favorites like H&M, Filene's Basement, Lerner New York, Forever 21, Nordstrom Rack, Urban Outfitters, Akira and T.J. Maxx.
12
Chicago Theatre

12) Chicago Theatre (must see)

The Chicago Theatre, originally known as the Balaban and Katz Chicago Theatre, is a landmark venue located on North State Street in the Loop area of Chicago. With a seating capacity of 3,880, it was promoted as the "Wonder Theatre of the World" when opened on October 26, 1921. Now listed as a Chicago Landmark and National Historic Place, the Chicago Theatre is a performing arts venue for stage plays, magic shows, comedy, speeches, and popular music concerts. Its iconic marquee, "as an unofficial emblem of the city", appears in film, television, artwork, and photography. The building stands seven stories tall and fills nearly one half of a city block. The interior shows French Baroque influence from the Second French Empire. The grand lobby, five stories high and surrounded by gallery promenades at the mezzanine and balcony levels, is influenced by the Royal Chapel at Versailles.

Why You Should Visit:
Ornate classic theater with an old-school ambiance; beautiful lobby and plenty of decorations to see inside before a show starts.
The daily 12 PM tour takes you throughout the building, its history, construction and curiosities, and you even get to go on the stage.

Tip:
There is much to do in the vicinity – shopping/restaurants/other theaters, so if you arrive too early, you can grab a bite or drink nearby.
Even if you don't see a show here, you have to at least snap a pic from the outside!
Sight description based on wikipedia
13
Michigan Avenue Bridge

13) Michigan Avenue Bridge (must see)

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!

Tip:
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
14
Wrigley Building

14) Wrigley Building (must see)

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 designed by the architectural firm of Graham, Anderson, Probst & White using the shape of 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.

Tip:
Tours of the building are available inside.

Opening Hours:
Mon-Fri: 8am-6pm; Sat: 8am-12pm
Sight description based on wikipedia
15
Magnificent Mile

15) Magnificent Mile (must see)

The Magnificent Mile, sometimes referred to as The Mag Mile, is an upscale section of Chicago's Michigan Avenue, running from the Chicago River to Oak Street in the Near North Side. Currently Chicago's largest shopping district, various mid-range and high-end shops line this section of the street; approximately 3,100,000 square feet (290,000 m2) are occupied by retail, museums, restaurants and hotels.

As a premier commercial district, The Magnificent Mile caters primarily to tourists and the affluent. Many of the world's leading retail stores populate the Mile, 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 Magnificent Mile, provide a variety of dining options, however, if you come to Chicago specifically for its famous pizza, then you should check out some of these locations: Gino's East River North – offering some of the best deep dish pizza experience in Chicago for half a century; Lou Malnati's – the home of the BEST Chicago-style deep dish pizza in the world!; and Pizzeria Via Stato – offering simple, no-fuss menu tavern pizzas, as well as small plates and seasonal salads made of market-fresh ingredients, complete with 300 Italian wines, and more – a casual hangout for River North locals and a delightful discovery for passersby.
16
Water Tower

16) Water Tower (must see)

The Water Tower was first built in 1869. It is one of the few constructions that survived the Great Chicago Fire of 1871. Today, the tower is considered a monument to that event. With its smaller Gothic-style towers, the Water Tower looks more like a tiny European 13th-century castle. Everyone is invited to make a stop at the Visitors' Center and the City Gallery nearby (the latter has free temporary exhibitions open to the public).

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

Tip:
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
17
Water Tower Place

17) Water Tower Place

Water Tower Place claims to be Chicago's premier shopping destination. It is a 758,000 sq ft shopping mall, featuring eight sophisticated levels and more than 100 of your favorite stores and restaurants, plus a mix of distinctive specialty shops and boutiques. Here, shoppers can have a unique, high-energy urban shopping experience.

Operation hours: Monday-Saturday: 10:00 am - 9:00 pm; Sunday: 11:00 am - 6:00 pm
18
John Hancock Center

18) John Hancock Center (must see)

John Hancock Center, located at 875 North Michigan Avenue in the Gold Coast area of Chicago, is a 100-story skyscraper constructed under the supervision of Skidmore, Owings and Merrill, with chief designer Bruce Graham and structural engineer Fazlur Khan. When the building topped out on May 6, 1968, it was the tallest building in the world outside New York City. It is currently the fourth-tallest building in Chicago and the ninth-tallest in the United States.

The Skydeck elevators of the John Hancock center, manufactured by Otis, travel 94 floors at a top speed of 1800 ft/min. From the 95th floor restaurant, diners can look out at Chicago and Lake Michigan. The Observatory (360 Chicago), which competes with the Willis Tower's Skydeck, has a 360° view of the city, up to four states, and a distance of over 80 miles (130 km). The Observatory has Chicago's only open-air SkyWalk and also features a free multimedia tour in six languages. The 44th-floor sky lobby features America's highest indoor swimming pool.

Why You Should Visit:
The views are exceptional as expected. There is a separate fee to experience TILT, which tilts you out 30 degrees over the side of the building and gives a breathtaking view of the skyline.

Tip:
Go for it when it's not cloudy/foggy to completely enjoy the experience.
Don't go for the TILT if you have a strong fear of heights!

Opening Hours:
Daily: 9am-11pm
Sight description based on wikipedia

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.
The Magnificent Mile Area Walk

The Magnificent Mile Area Walk

The Magnificent Mile is located between the Chicago River and the Lake Shore Drive. It is considered one of the great avenues of the world, being Chicago's version of the Champs-Elysees. Take this walk to explore the Magnificent Mile boulevard and the surrounding area, that features a wide selection of amazing shops, world-known museums, restaurants and spectacular architecture.

Tour Duration: 2 hour(s)
Travel Distance: 3.4 Km or 2.1 Miles
Architectural Walking Tour in The Loop District

Architectural Walking Tour in The Loop District

Chicago features an outstanding architectural legacy. This city has long been connected with some of architecture's most important names: Frank Lloyd Wright, Louis Sullivan, Mies van der Rohe, and Holabird & Root. The Loop District offers an extensive number of Chicago's famous architectural "must-see" buildings such as Aqua Tower, Willis Tower, Chicago Theatre, or Rookery...  view more

Tour Duration: 3 hour(s)
Travel Distance: 4.6 Km or 2.9 Miles
Discovering Chinatown

Discovering Chinatown

Located in the Armour Square, the Chinatown in Chicago was first established in 1912. It is considered the best example of American Chinatown. Here, you will find a wide range of unique boutiques, specialty shops, amazing religious buildings, Chinese medicine stores and Chinese restaurants. Take this walking tour to discover Chicago's Chinatown.

Tour Duration: 1 hour(s)
Travel Distance: 1.7 Km or 1.1 Miles
Souvenir Shopping Part 1

Souvenir Shopping Part 1

It would be a pity to leave Chicago without having explored its specialty shops and bringing home something truly original. We've compiled a list of gifts and souvenirs, which are unique to Chicago, that a visitor might like to purchase to reflect their visit.

Tour Duration: 1 hour(s)
Travel Distance: 2.0 Km or 1.2 Miles
Best Jazz and Blues Clubs Tour

Best Jazz and Blues Clubs Tour

Chicago is considered to be one of the most important destinations where Jazz & Blues developed. In the 1920s this city became a center of hot jazz. At the same time blues started to invade Chicago. So if you are a fan of Jazz and/or Blues or you simply like listening to great music, take this walking tour and don't miss the chance to visit some of the best Jazz & Blues clubs in...  view more

Tour Duration: 1 hour(s)
Travel Distance: 3.0 Km or 1.9 Miles
Art Galleries Tour

Art Galleries Tour

The art world in Chicago is considered vast. There is a large number of art galleries in this city and each gallery has its own unique setup and outstanding exhibitions on display. The beautiful galleries feature works in a wide range of fields, from up-and-coming artists to famous artists like Pablo Picasso. Take this walking tour to explore some of the most famous galleries in Chicago.

Tour Duration: 1 hour(s)
Travel Distance: 3.0 Km or 1.9 Miles

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