Will Hide sings the praises of American’s second city

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Frank Sinatra’s rendition of New York, New York may be the ditty that gets drunkenly belted out at all sorts of celebrations, but look on YouTube and we think Ol’ Blue Eyes puts even more heart and soul into Chicago – My Kind of Town.

And why not? Like many second cities – think Melbourne to Sydney, Manchester to London or Barcelona to Madrid – it has heaps of things to see and do, hospitable locals and fantastic dining. Welcome to the Midwest.


06.00: Awake early with jetlag? Do what thousands of locals do each morning – go for a run or walk along the path by Lake Michigan.

08.00: Breakfast time. Try a fig omelette or tiramisu pancakes at Wildberry Cafe (wildberrycafe.com) or mascarpone-stuffed French toast with strawberries and chocolate at the appropriately-named Toast (toast-chicago.com).

09.00: Get your Chicago bearings on the leisurely seven-mile guided Lakefront Neighbourhoods Tour with Bobby’s Bike Hike (bobbysbikehike.com). The level is billed as ridiculously easy and guides are great fun with tons of local knowledge. Highlights include Oprah Winfrey’s house, the Playboy Mansion and Lincoln Park Zoo.

12.00: Forget burgers – Italian beef sandwiches are a local delicacy. Look for mini chain Al’s Beef (alsbeef.com) for the thin slices of seasoned roast beef dripping with juices and served in a roll.

13.00: Even if you’re not really into art, you will definitely want to check out the Art Institute of Chicago (artic.edu). It’s chock-a-block with paintings by Matisse, Degas, Picasso and others that you will have seen dozens of times on TV or in print – but all of a sudden, here they are just a foot away. Nearby in Millennium Park take a photo of yourself in the reflection of ‘the bean’ (pictured below), the artwork by Anish Kapoor that is properly called Cloud Gate and which has, since its conception a decade ago, become an instantly-recognisable and highly-polished symbol of the city.

16.00: A trip to the States without hitting the shops? Well that would simply be un-American. Mooch along the Magnificent Mile (themagnificentmile.com), aka Michigan Avenue, for brands such as Banana Republic, Nike and Levi’s. While there, grab a tin of Garrett’s popcorn to take home (garrettpopcorn.com). Its Chicago mix combines caramel and cheese and is beyond addictive.

19.00: Chicago has more Michelin award-winning restaurants than any other city in the US, but if you a want a table at the likes of super-hip Alinea (alinearestaurant.com) or Next (nextrestaurant.com), get planning months before you leave. Other thoughts? Try Grace (grace-restaurant.com) – chef/owner Curtis Duffy was head chef at Alinea – or Little Goat (stephanieizard.com), a contemporary American diner, and both very in. Accessible alternatives for posh nosh might include Boka (bokachicago.com) and Naha (naha-chicago.com).

23.00: Are you having a laugh? You will do at Second City (secondcity.com), the legendary comedy club that has launched the careers of the likes of John Candy, Jim Belushi, Tina Fey, Jane Lynch and Steve Carell. There are late-night shows at weekends and there’s always a chance famous alumni will tread the boards.



10.00: After a lie in, hop on Chicago’s elevated urban railway, the L (transitchicago.com), to the Damen stop in trendy Wicker Park for brunch at sublime Mindy’s Hot Chocolate (hotchocolatechicago.com). Try the warm homemade doughnuts or pancakes with strawberry butter. Afterwards, the same street has some interesting shops, for example the T-Shirt Deli (tshirtdeli.com) where you can have all sorts of shirts custom-printed then packaged like a take away meal, which make great presents.

13.00: Back downtown for a 90-minute guided architectural boat tour of Chicago’s famous skyline (cruisechicago.com). Sounds a bit yawn-worthy? Not at all – the guides really inject warmth into their subject and you’ll soon agree that the Chicago skyline from the water makes certain other American cities look a bit like Tunbridge Wells. New for this year is a Capture Chicago Photography Cruise.

16.00: Like living on the edge? Head up the Willis Tower to the Skydeck (theskydeck.com) – glass ledges jut out from the side of the building and there’s nothing between you and the pavement apart from some reinforced glass and 1,353ft of air. For another perspective on the city’s impressive buildings head up the John Hancock Observatory (jhochicago.com) across town, 1,500ft in the clouds.

19.00: Time for dinner. You did upmarket last night, so tonight indulge in another local tradition – deep dish pizza. Your arteries may not thank you, but your taste buds will be your best friend forever. Chicago-style pizza has a crust up to three inches high, with lots of chunky, tasty tomato sauce. Don’t expect a thousand variations – your basics are the cheese and tomato, the sausage or the pepperoni. Look out for a branch of Uno (unos.com) or Lou Malnati’s (loumalnatis.com), both of which have claims to inventing the original back in the 1940s.

22.00: If you’ve still got room, perhaps a post-dining cocktail in one of Chicago’s hundreds of bars? Timeoutchicago.com or choosechicago.com should point you in the right direction. Best of all, ask a friendly local. The city’s drinking scene covers everything from dive pubs to hipster-fabulous and speakeasy-swanky, with plenty of neighbourhood joints thrown in.

23.00: Round things off with some soulful tunes at the Jazz Showcase (jazzshowcase.com) in the South Loop neighbourhood, or the Green Mill (greenmilljazz.com) on North Broadway Avenue. The latter has sessions until 5am on Saturday nights. In fact, depending on your jetlag, you could just head straight out for another sunrise jog along Lake Michigan.choosechicago.com