How to see Chicago in three days

It’s a vibrant, electrifying city, one that inspired songs such as Sinatra’s My Kind of Town (Chicago Is), a US centre of the arts and sports which offers many top-rated restaurants.

Chicago, on the southwestern shore of Lake Michigan, boasts sculptures by Pablo Picasso and Joan Miro, towering skyscrapers by famous architects, expansive parks, fantastic museums, and blues and jazz music in the bars.

Here’s how to see and do it all in three days

Chicago River boat excursion for architecture buffs

In bygone days, the Chicago River was like a stinking sewer. Early residents built their houses facing away from the river because it stank so much. Today, the river is a jewel and one of the top addresses for apartments that, overlooking the scene, cost a fortune to buy or rent.

An excursion boat of the Architecture Foundation takes visitors on a tour that shows a city in transition – old warehouses that have been converted to exclusive apartments and huge skyscrapers such as the Willis Tower (previously the Sears Tower).

At 442 metres, the building by architect Fazlur Khan (1929-82) is the second-tallest in the United States.

Touring the Astor Street District with a “Chicago Greeter”

“I would love to show you the Astor Street District,” a man named Wally calls out to visitors. He is a volunteer working for Chicago Greeter, an organisation where local residents show their city to tourists – for free.

On this particular day, Wally is showing a district of elegant brownstone buildings, art-deco houses and historic residents of Chicago’s high society. Among others, there is the first Playboy Mansion, where men’s magazine publisher Hugh Hefner hung out.

Built in 1899, it has about 70 rooms.

Then there is the Public Hotel, in former days called the Ambassador East, the place where Frank Sinatra stayed when in town.

Recreation and Art in Millenium Park

Millenium Park, opened in 2004, is an oasis of greenery in the middle of the city. Crowds of people will surge into the park in the summer for concerts in the Jay Pritzker Pavilion. On the park’s edge is Crown Fountain, where two towers each about 15m high project videos of peoples’ faces, with water pouring out of their mouths.

Arguably the most popular spot for selfies is at Cloud Gate and its striking bean-shaped sculpture by British artist Anish Kapoor. The locals simply call the shining stainless-steel object The Bean – for fairly obvious reasons.

The Blues and Jazz bar scene

For those who like blues and jazz, Chicago is heaven. In the downtown area, musicians will often set up their drum kits and play for the passing crowds, while typical Chicago Blues music can be heard coming from the city’s many bars and restaurants.

The city’s blues and jazz history reads like a hall of fame of top musicians such as Buddy Guy, Willie Dixon and Little Walter. Some top spots to head to are Buddy Guy’s Legends, Andy’s Jazz Club and the Chicago B.L.U.E.S. bar.

Wining and dining

Chicago’s dining scene is international and the choice of restaurants is huge – as are the portions served. A tasty breakfast, be it sweet pancakes or ham and eggs or omelettes, awaits hungry visitors at the Wildberry.

Steak lovers will head to Gene and Georgetti’s, established in 1941.

Those who like oysters, crabs and fish dishes will seek out Shaw’s Crab House, where in the evening there is always live music in the bar area.

Visitors will want to try the legendary Chicago-style pan pizza, thick as a quiche. Bacino’s restaurant is a good spot to order one.

Art attack

Everywhere you go in Chicago, you’re bound to run into some open-air artwork. At Daley Plaza there is a sculpture by Pablo Picasso, and at Brunswick Plaza the one by Miro.

Of the city’s museums, the Art Institute Chicago is the most internationally renowned, with works by Claude Monet, Marc Chagall, Henri Matisse, Picasso and Gerhard Richter. Also a must for art lovers is the Museum of Contemporary Art, with a collection that includes works by Joseph Beuys, Andy Warhol and Francis Bacon.

Breathtaking views from above

Those seeking a breathtaking view of the huge city have two skyscrapers in the downtown area to choose from. At the 360 Chicago, a viewing area on the 94th floor – some 300m up – offers a fantastic panorama of Lake Michigan and the Navy Pier.

Then there is the skydeck on the 103rd floor of the Willis Tower – 412m up. For an adrenaline thrill there are glass-floored balconies with straight-down views.

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