Chicago Illinois, located in the mid west USA on Lake Michigan, is a city with a lot of history, great architecture, excellent restaurants and very friendly people. It is a smaller, nicer version of New York City, and second most visited city in the US after NYC. It has a pleasant small town vibe (even with the 3d largest population in the USA), but with the sophistication of an urban metropolis. Chicago is an international hub for finance, commerce, industry, technology, telecommunications, and transportation.

Chicago is the birthplace of the skyscraper and considered the most influential architectural city of the 20th century. The skyline punctuated by skyscrapers such as the iconic John Hancock Center, the Willis Tower (formerly the Sears Tower), the Wrigley building, and the neo-Gothic Tribune Tower.

The city is also renowned for its museums, including the Art Institute of Chicago with its noted Impressionist and Post-Impressionist works.

Chicago Skyline

Things to do

In most cities, we recommend the hop on hop off tour buses. It’s a good way to get to many attractions and really see the city.  Here are some key places to visit:

Architecture boat tour

We took the Wendella Architecture Boat Tour along the Chicago River and loved it. The guides are very knowledgeable about the history of Chicago architecture and present the stories in a fascinating way. The tour lasts about 90 minutes. They serve drinks. For photography take the tour an hour before sun set – at dusk. My photos from the boat were taken at dusk and then the last ones were at night (it was too dark for the evening shots without a tripod).

Chicago River at DuSable Bridge

For more photos from the boat tour go to my photography site: Wonderland Photography.

Macy’s

Chicago has the flagship Macy’s store, but the reason to go there is to view the interior. It is gorgeous! Plus they always have good deals on clothing and accessories.

Macy’s famous ceiling

For fans of the Blues, you cannot skip Chess Records and the Willie Dickson Blues Museum. This, and Sun Records in Memphis, is where Rock n’ Roll started. It is closed on Sunday and Monday.

Chess Records
Willie Dixon’s Blues Museum

Millennium Park

Millennium Park consists of a civic center and huge park with many points of interest and open green lawns. The site holds a variety of public art plus the Jay Pritzker Pavilion, a band shell designed by Frank Gehry and the McCormick Tribune Plaza and Ice Rink which is used for public events. Other highlights of the park include the Wrigley Square, site of the Millennium Monument; Harris Theatre and the Crown Fountain, an interactive video art piece where faces of Chicago residents are displayed on huge towers and fountains rise up from a black granite floor where people can play in the water. The Crown Fountain also features two waterfalls cascading down 15 meter high walls of glass bricks and dancing lights. The park is connected to the northwestern section of Grant Park by the BP Pedestrian Bridge and Nicholas Bridgeway.

Grant Park

Agora is an installation of 106 headless and armless iron sculptures at the south end of Grant Park in Chicago. Designed by Polish artist Magdalena Abakanowicz, they were made in a foundry near Poznań between 2004 and 2006. In 2006, the Chicago Park District brought the work to Chicago as a permanent loan from the Polish Ministry.

Art Institute of Chicago

The art held at this museum is truly some of the best in the world. The permanent collection consists mainly of impressionist and post-impressionist work but there is also a fantastic collection of American art, decorative arts, modern, contemporary and Asian art as well as European Old Masters. There is a photography collection, ancient art, armor from the Middle Ages, architectural elements, prints, textiles and a room devoted to miniatures.  The museum is spread over eight buildings and is the second largest art museum in the USA after the New York Met.

Highlights of the museum include 30 paintings by Monet and works by Renoir, Cezanne, Picasso, Matisse, Magritte, Toulouse-Lautrec and Van Gogh. Among the outstanding works by van Gogh there is his Self-portrait and Bedroom in Ares. Among the collection of American works there are pieces by Mary Cassatt, Edward Hopper and James N. Wood. The American Decorative Arts Gallery includes furniture designed by Frank Lloyd Wright and in the ancient civilizations section there are Egyptian, Greek and Roman galleries. There is a powerful African American Art Collection where the progress in civil rights can be traced through the historical works of art and illustrations.

Chicago Art Institute

Willis Tower Skydeck

The tower has 110 floors and stands at 442 meters above the sidewalk; it is one of the tallest buildings in the world. You can walk on one of the retractable glass balconies which extend 1.2 meters out of the façade, and look through the floor all the way down.

John Hancock Building

The former John Hancock Observatory is an observatory deck at the top of the John Hancock Center on Chicago’s Magnificent Mile. The latest addition to the activities at the observatory is the 360 Chicago Tilt. Eight visitors at a time stand on a platform which juts out and over the edge of the building. They stand facing a floor to ceiling glass wall and then the wall tilts downwards 30° so that the visitors can see not only out but directly down. The reinforced box consists of a tipping box, eight windows, bars to hold on to and a lot of steel.

Chicago River and Skyline – John Hancock building

More things to do:

  • Magnificent Mile
  • Navy Pier
  • Lakefront Trail
  • Shedd Aquarium in Grant Park – one of the largest in the world
  • The Field Natural History Museum in Grant Park
  • Museum of Science and Industry
  • Lincoln Park Zoo
  • The Chicago Theatre
  • Chicago Crime Tours
  • Museum of Modern Art
  • Wrigley Field
  • Frank Lloyd Wright Residence
  • Rookery Historic Building
  • Marina City Building
Marina City Condos

Marina City was designed by visionary architect Bertrand Goldberg and completed in 1962. Perched on the edge of the Chicago River, the all-concrete complex suddenly made it cool to live downtown and included innovative amenities such as an on-site grocery store, bowling alley, and marina. The twin towers’ famous corn cob shape make the duo an instantly recognizable Chicago icon. Featured in the Blues Brothers movie.

Wrigley Building

Evening Entertainment

For entertainment, there are a lot of great venues. We went to Buddy Guy Legends and Andy’s Jazz Club. Many restaurants feature live music so you can plan a dinner and see a show at the same time. If you want to see great Blues, you have to go early to get a seat because they are often small venues and fill up quickly.

Buddy Guy playing at his club Legends

Other Blues & Jazz venues:

BLUES Bar
Andy’s Jazz Club

And you can just wander around the streets of Chicago to enjoy the pleasant atmosphere.

In front of Chicago River and Wrigley building at DuSable Bridge
Chicago Tribune Building
Men’s Athletic Association Hotel
Jewelers Building and Stratosphere Lounge – the lounge was an Al Capone hang out.
The Chicago River – it really is that green!
The Loop with the elevated subway train
333 Wacker Drive office building
London Guarantee Building 1923 and Jewelers Building (35 East Wacker) camera right
Chicago Tribune Building and Apple store
Navy Pier

Public Art

Throughout downtown there are many beautiful art installations. Miro, Picasso and other artists have their worked sprinkled all over the Loop and vicinity.

Calder’s Flamingo
Picasso
Cloud Gate aka “The Bean”
Miro

Where to Stay

I think the best area to stay in is Near North (Magnificent Mile with a lot of great restaurants is located here) or North East part of the Loop. There are a lot of hotels in this area. We stayed at the Virgin Hotel. The staff is super friendly and the room layout is excellent; nice and spacious with good lighting for makeup. And they don’t charge extra fees or nickel and dime you. Room service is reasonably priced with no delivery fee, and the treats in the room are at retail prices.

Our room at the Virgin Hotel
Lobby at Virgin Hotel

Where to Eat

Bar at Virgin Hotel

Chicago has a lot of great restaurants. It was hard to pick and choose just a few.

The famous Shaw’s Crab House

Enjoy your visit to Chicago!

Chicago waterfront and skyline