The Real Chicago: Guide to the Windy City

Photo: Saisiva Sababathy via Flickr

This post is brought to you by Sarah.

Even though Chicago may have gained recognition as the stomping ground of infamous prohibition-era gangster Al Capone and the star of TV’s Married… with Children Al Bundy, America’s second city has a lot more to offer.

Situated on Lake Michigan, Chicago is the home of blues and jazz music and continues to be a leading cultural hub. In addition various festivals, theatres, dance shows and art exhibitions, the Windy City also has professional sports teams in each of the major professional leagues.

What’s more, the city is a celebrated centre of architecture, with an impressive skyline consisting of notable Chicago hotels, imposing skyscrapers and famous landmarks. So what shouldn’t you miss if you take a trip to the Windy City this year?

Navy Pier

Chicago’s number one attraction is Navy Pier, situated just east of the downtown area. Originally designed as a shipping and recreation facility, today Navy Pier showcases a plethora of restaurants, shops, museums and fairground attractions.

Crystal Gardens is a 32,000 square-foot indoor botanical park, while in high season performers such as jugglers, mimes, comedians and musicians can be found all the way along Dock Street.

Willis Tower (formerly known as Sears Tower)

On a clear day, visitors to one of the tallest buildings in the world can see Michigan, Wisconsin and Indiana up to 50 miles away. Although Willis Tower is a working office building, tourists can take advantage of this engineering and architectural triumph.

Visit the Skydeck for multimedia lessons about Chicago’s history, music, literature and sport. Here you’ll also be able to truly appreciate the tower’s soaring presence, as a five-sided glass box known as ‘The Ledge’ enables visitors to look down straight down to the ground 1,300 foot below. Lift queues to the 103rd floor can get fairly lengthy, as 1.5 million tourists make this journey every year, so make sure you get in early!

Millennium Park

Millennium Park is another popular attraction among tourists and locals thanks to contemporary architecture, landscape design and art. Located in the heart of the city, this 10-hectare recreational area often hosts concerts, exhibitions, tours, family activities and other cultural programs.

Sights to look out for include Frank Gehry’s winding BP Bridge, Jaume Plensa’s 50 foot-tall towering glass Crown Fountains and Anish Kapoor’s bean-shaped Cloud Gate.

Art Institute of Chicago

Boasting one of the world’s largest art collections, with examples spanning 5,000 years, the Art Institute of Chicago is well worth a visit. From antiquities to modern times, exhibits are changed and updated every few months, covering different time periods and artists each time.

The prominent African & Amerindian collection includes wood sculptures, masks, ceramics, furniture and textiles. European paintings range from the Middles Ages to 1900, with French 19th century pieces taking centre stage.

So if you’re one of the ones who instantly think of famous people or fictional characters when somebody mentions Chicago, remember that there’s an abundance of cultural attractions and fun activities to enjoy in America’s third largest metropolis.

9 thoughts on “The Real Chicago: Guide to the Windy City”

  1. The Art Institute of Chicago is brilliant, I have been there before and I can honestly say it is a place I would revisit every time when I go back, great place for the kiddos too.

  2. We’ve travelled frequently to Chicago – my husband is from there and has family still there. We stayed downtown one of the trips and use the CityPass for Chicago to get multiple museums, aquarium, and tower entrance. It was a good deal and a fun trip!

  3. I live in Chicago and highly recommend it to any and all welcome visitors. There’s plenty to see and do in the city.

  4. I was in Chicago once in 1968 to watch my husband graduate from Boot Camp. H was in the Navy and it was in the winter. It was so cold we couldn’t go anywhere. Would love to go again but in the Spring or Summer months.

  5. I’ve always wanted to see Chicago – but the closest I’ve come is flying over it. It seems that it has so much to offer – I’d like to check out the Navy Pier, it sounds similar to NYC’s South Sea Seaport, which I always love to visit! One of these day….I hope….


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