Blown away by the Windy City

Chicago – home to the notorious Cook County jail, the whisky-stained underground blues and jazz scene, skyscrapers that stretch into the clouds as far as the eye can see, the Magnificent Mile, and, of course, a whole feast of homegrown, iconic foods. So with only a long weekend available to pack in as much as possible, what will you choose?

Chicago Skies

Chicago has one of the most dramatic skylines of any American city, shaped by two standout structures – the John Hancock Building and the recently renamed Willis Tower. Known as Sears Tower until 2009, this structure is the tallest building in America and was the tallest in the world for 25 years. Standing right up against the glass of the sky deck, it almost feels as though you are Jack standing in the clouds after climbing up the beanstalk. The 360° view which greets your eyes is incredible. Far down below is a maze of tower blocks, sports stadiums (including the impressive Soldier Field, home of the Chicago Bears), Lake Michigan reaching out for miles, and a curious buzz of activity by the pier – Navy Pier.


Navy Pier is a lively, exciting area; go for some food, a few drinks, to watch some theatre, to chill out on the Ferris Wheel with an ice cream from one of the many friendly vendors, or even to take a sightseeing cruise on Windy the Tall Ship. There are also a few clothing and souvenir shops, but if you are a shopaholic then don’t dither about here – you need to hail a yellow cab and tell the driver “to the Magnificent Mile!”

The Magnificent Mile is a shopper’s paradise. One whole mile, bursting with every shop that you could possibly imagine, and more! You could easily spend a whole day here, but with so much else on offer, try to hold yourself back!

The Famous Food

Whilst in Chicago you will experience many culinary treats, but if you want to try something truly authentic, cruise downtown, head to the nearest pizza house, and order one slice of their deep-dish pizza pie. Believe me, one slice is more than enough of this cheesy and seemingly upside-down delight.

Whilst downtown (and to walk off all of the pizza sitting inside you!) take a wander and you are sure to stumble upon some old, cracked and crumbling buildings, but before you dismiss them, take a closer look. You will more than likely discover that it is an old blues and jazz bar, brimming with character and melody, exploding in perfect harmony.

Other Attractions

If this doesn’t appeal to you until the sun has gone down, then walk over to Millennium Park so you can write home that you have seen The Bean. Definitely worth a visit, this sculpture (really named Cloud Gate) is like a gigantic, 3D, kidney bean-shaped mirror, and is the second most popular tourist attraction in the city.

Although by the end of your stay you may feel as though you have taken an overdose of urban life, do not be tricked into thinking that that is all there is. Chicago is a city stuffed with arts, culture, sport, music, education, architecture, and, luckily for you, it’s not going anywhere.