This vibrant, electrifying city inspired Sinatra's My Kind of Town and is also a top spot for high-quality restaurants, writes Claudia Steiner.

Chicago, on the southwestern shore of Lake Michigan, boasts sculptures by Picasso and Miro, towering skyscrapers, expansive parks, fantastic museums, and blues and jazz music. 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. Today, it is a jewel and one of the top addresses for apartments that cost a fortune to buy or rent. An excursion boat of the Architecture Foundation shows a city in transition - old warehouses that have been converted to exclusive apartments and huge skyscrapers such as the 442m Willis Tower (previously the Sears Tower), the second-tallest in the US.

Touring the Astor St District with a "Chicago Greeter"


Volunteers show their city to tourists, free. Among the highlights are elegant brownstone buildings, art-deco houses and historic residences of Chicago's high society. Then there is the 70-room Playboy Mansion, where Hugh Hefner hung out, and the Public Hotel, formerly the Ambassador East, where Frank Sinatra stayed.

Recreation and art in Millennium Park

Millennium Park, opened in 2004, is an oasis of green. On the park's edge is Crown Fountain, where two towers project videos of people's faces with water pouring out of their mouths. A popular spot for selfies is at Cloud Gate and its bean-shaped sculpture by British artist Anish Kapoor.

The blues and jazz bar scene

In the downtown area, musicians will often set up their drum kits and play, and Chicago Blues can be heard coming from many bars and restaurants. Chicago's history reads like a hall of fame of top musicians such as Buddy Guy, Willie Dixon and Little Walter. Top spots 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. Steak lovers should head to Gene and Georgetti's, established in 1941. Those who like oysters, crabs and fish dishes will enjoy Shaw's Crab House. Visitors will want to try the legendary Chicago-style pan pizza, which is as thick as a quiche.

Art attack


Everywhere you go you're bound to run into open-air artwork. At Daley Plaza is a sculpture by Pablo Picasso, and Brunswick Plaza boasts work by Miro. The Art Institute Chicago is internationally renowned, with works by Monet, Chagall, Matisse, Picasso and Gerhard Richter. Also a must is the Museum of Contemporary Art, with a collection that includes works by Joseph Beuys, Andy Warhol and Francis Bacon.

Bird's-eye views

Those seeking a view have two skyscrapers to choose from. At the 360 Chicago, a viewing area on the 94th floor - 300m up - offers a panorama of Lake Michigan and the Navy Pier. Then there is the skydeck on the 103rd floor of the Willis Tower - 412m up.