Chicago: my kind of town

By | Category: Travel destinations

The Windy City will, ahem, blow you away writes Kaye Holland

“Each time I leave, Chicago is tugging my sleeve
Chicago is The Wrigley Building,
Chicago is The Union Stockyard,
Chicago is one town that won’t let you down
It’s my kind of town”

So sang Sinatra back in 1964. Old Blue Eyes wasn’t wrong. Nowhere beats Chicago – both metaphorically and literally (it’s the home of the skyscraper). The Windy City is one of those rare places that looks stunning at any time of year: it boasts art and culture, professional sports, world class museums, hip hotels and restaurants plus the sort of energy that only a city has. Little wonder then for many who come, Chicago immediately becomes their favourite American metropolis. True it’s a long way to go, but then then finest things in life are not always the easiest to achieve. Got your passport? Good. Now read on for the low-down on where to eat, shop and play.

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Must see and do
The skyscraper was born in Chicago and as such high rise buildings abound but the two most iconic are arguably 360 Chicago and the Willis Tower. The former boasts million dollar views of the lovely lake and also a fabulous 96th floor bar – the perfect place to enjoy a sky high drink. The latter was the Sears Tower until 2009 when it was purchased by insurance broker, Willis Group Holdings. Many Chicagoans continue to refer to the structure as the Sears Tower but regardless of what the Tower gets called, the fact remains that at 1454ft it is the tallest building not only in the Windy City but in the whole of America – so prepare to be blown away.

Haven’t got a head for heights? Make for Millennium Park  – packed as it with free art sights from Frank Gehry’s BP bridge to Jaume Plensa’s Crown Fountain. The 50ft fountain is famous for its video images of locals spitting water. However Millennium Park’s big headline grabber is the Cloud Gate – aka ‘the bean’ – a silver drop sculpture that’s the brainchild of Anish Kapoor.

The Bean

The Bean

If museums are more your bag, don’t miss the impressive Field Museum of Natural History that houses, among other artifacts, the largest Tyrannosaurus, ever found. For further culture, check out the Art Institute of Chicago – it’s chock full of paintings by Picasso, Matisse, Degas and dozens of other big names. Then look to the Harold Washington Library downtown – a beautiful post modern tribute to the city’s cultural and academic pursuits. Inside you’ll find inspirational quotes such as Victor Hugo’s  “A library implies an act of faith, Which generations still in darkness hid, Sign in their night in witness of the dawn” adorning the marble walls – as well as some fantastic public exhibitions.

Lastly if you’re in town during the summer on a Saturday or Wednesday evening, wander to Navy Pier – Chicago’s most visited attraction. The half mile peer is unabashedly touristy (the chain gang have all set up shop here) but the firework displays  (9.30pm on wednesdays and 10.15pm on saturdays) and lovely lake views more than compensate.


Top shops

American Girl

American Girl

Ready for some retail therapy? Make for the Magnificent Mile shopping strip (also known as Michigan Avenue)  for all your favourite American stores: think Saks,Tiffany’s, Macy’s, Bloomingdales and Abercrombie and Fitch. If you’re travelling with tweenage  girls, don’t miss American Girl Place. Little princesses will love this multi story dolly department store where they can stock up on accessories for their plastic offspring and even purchase a matching outfit. Consumerism gone mad? Perhaps but this girl power palace is a sight worth seeing while in Chicago.



Deep dish pizza

Best bites
Chicago has all the restaurants and cafes that the international classes expect but apply the ‘never eat what you could have at home’ rule and order a deep dish pizza (a true Chicago speciality). A three inch pizza crust piled with gooey cheese and chunky tomato sauce sounds as though it shouldn’t work: it does. Pizzeria Uno claims to have invented the deep dish concept in 1943. Alternatively go to Gino’s East, Giordano’s or Pizano’s (Oprah’s favourite) for a piece of pie.

But it’s not all about pizza. The Windy City is also the home of the iconic Chicago hot dog and the queues for the Chicago version (a ‘dog’ that’s drowning in every topping imaginable save ketchup) at joints such as Hot Doug’s are equal to those of any North American restaurant. Italian beef sandwiches – thin sliced, slow cooked roast beef slathered in gravy and stuffed in a sub – are the third local delicacy. Who serves the best beef sandwich? That would be Mr Beef (666 N Orleans Street) – you’ll find it four blocks west of Hotel Felix.

Modern day Chicago is also a world class restaurant capital  with more more Michelin award-winning restaurants than any other city in the US. Be prepared to battle to get a booking at the likes of Alinea (superstar chef Grant Achatz’s temple to molecular gastronomy) but, if you get one, you won’t be disappointed.


After dark
I’m not normally one for sticking to the safe parameters of a hotel bar but oh – the hotel bars in Chicago! They’re so swanky that it’s worth ditching any silly self imposed rules about not hanging out in hotels. The bars in The Congress Plaza, Palmer House and The Drake have been the destinations of choice for everyone from royalty (the Queen) to world leaders (Roosevelt and Ghandi). Bring on the bling….
Alternatively seek out a speak easy bar such as the glamorous Green Mill. This was Al Capone’s favourite gin joint (you can still see the tunnels underneath the bar where he once stashed his booze). Today the Green Mill is a good spot to enjoy live jazz (Mon-Sat) and acclaimed poetry slams (Sun).

Billy Goat Tavern

But no visit to Chicago is complete without dropping in at the scrappy Billy Goat Tavern. This Chicago dive bar is where the curse of the Cubs began. Basically Billy Goat’s owner, Billy Sianis, attempted to enter Wrigley Field with his pet goat in 1945. Sianis and his smelly animal were refused entry and an outraged Sianis declared: “Them Cubs, they ain’t gonna win no more.” Cub fans believe the curse still exists: they haven’t won a National League pennant since Sianis’ statement. For more on the Cubs curse (and other local stories) check out  the Tavern’s newspapered walls but factor in plenty of time: the night ended when I glanced down at my watch and noticed it was nearly 2am – which can happen in Chicago if you’re not careful.

Wrigley Stadium

Chicagoans are fanatical about their sport but there’s only one team that really matters: take a bow the aforementioned Chicago Cubs. This much loved Chicago baseball team inspires an almost religious following (despite the fact that they last won a world cup series in 1908) and a trip to see The Cubs play at the charming Wrigley Field stadium (famed for  its classic neon entrance sign and ivy walled field) should rank high on any Windy City itinerary. Even if you’re not a baseball fan, it’s worth going for the atmosphere alone and potential chance encounters with Cubs’ legends. I attended a Cubs v Phillies match in April where the highlight was meeting former Major League Baseball right handed pitcher, Fergie Jenkins.


Jenkins dispensed gossip and life wisdom with fans throughout the match. Why is he so generous with his time? “My Father always told me that you meet the same people on the way up in life, as you do on the way down. It’s hugely important to give back. We must all remember this.” Would the likes of Luis Suárez, Carlos Tevez and John Terry please take note…


Just About Travel’s Kaye Holland (right) chats to Chicago Cubs’ baseball legend, Fergie Jenkins


Where to stay
The Intercontinental Chicago Magnificent Mile has timeless traditions and decades of experience of welcoming visitors: the staff shower you with the sort of attention that makes you feel – if only for a few days – that you have entered a different world. Plus its downtown location is ideal for getting a sense of the city.


Getting there
Chicago O’Hare International Airport is located 17 miles north west of downtown Chicago. The cheapest way to reach the city centre is on the CTA blue line but if you don’t fancy taking the train, a cab will cost around US$50. Another option is to take the Airport shuttle.


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