Top 10 Chicago highlights

'If there is anyone out there who still doubts that America is a place where all things are possible,' begins Barack Obama, '…tonight is your answer.' But in the frosty, electric air above Grant Park we’re not just anywhere in America: we’re in Chicago; a place where all things are possible. Here are ten of the best ways to spend your time here.

1. Plug in and hear the windy city wail

Chicago may have launched a huge number of musical movements, but none are as iconoclastic as the blues – a rude, raunchy, radically inspired take on the genre that’s defined by screaming guitars, rolling bass lines and R&B-inflected rhythms. Today, modern blues makers have adopted a funkier gait and more cocksure vocals than their predecessors, but no visit to the city would be near complete without seeking out a blues hall and getting the blues in person.

2. Heft a gooey slice of the city’s infamous Ambassadorial dish

You almost have to feel a little bad for the first pizzas in Chicago – a scrawny, sickly disk of baked dough that was hardly fit to carry the locally packed pork sausage that burdened its surface. But in the early 1940s Chicago’s famed take on the dish – a true pizza pie – fell from the heavens with a thud. These behemoths are little like the pathetic comfort food known by the same name in the rest of the world; they’re created in a special pan – kind of like a frying pan without the handle – so the dough, which encases a molten bed of mozzarella, tomato sauce and a heart-stopping collection of meats, can be oven fried.

3. Spend a day in the playful heart of the city

The colossal head of a crazy-looking old lady – four stories high! – is spewing a gush of water onto a gaggle of squealing children. In the distance, the spires of the city rise into the clear blue air, along which floats a faint orchestral strain. Sure, you could get on the El and spend the day racing around the city by foot, but you’d probably learn just as much about the character of the city by spending a long, lazy afternoon soaking in the city’s centerpiece, Millennium Park.

4. Stroll among impressionists, armour and American masterpieces

You’ve passed the big bronze lions and entered one of the premiere art museums in the modern world: endless marble and glass corridors, room after room after room filled with paintings, textiles, sculpture and photographs – some quarter of a million in total – all of which demands ponderous chin-stroking hours of appreciation.

5. Take me out to the ballgame… and conciliatory beers afterward

Set to a soundtrack of hollering sports junkies and high-fiving beer drinkers, a visit to Wrigleyville is a boisterous Chicago experience that’s completely off the hook if the Cubs are at home. Built in 1914 and named for the chewing-gum magnate, Wrigley Field – aka ‘The Friendly Confines’ – is the second-oldest park in the major leagues, where a tangible sense of the ivy-covered history comes alive with legendary curses, playful traditions and a team that suffers some of the worst luck in US sports history.

But no matter that the hapless Cubbies haven’t won a championship since 1908, shoveling down hot dogs with the riotous ‘Bleacher Bums’ makes for an unforgettable afternoon.

6. Convene with silverbacks and roaches at the city’s best freebie

Situated in the heart of the park and bordered by Lake Michigan, Lincoln Park’s ‘zoological garden’ positions the oldest animal park in the US among rolling brick pathways and a jubilant display of flowers, making it one of Chicago’s great remaining freebies.

7. Float in the shadow of concrete and steel giants

Sure, it’s possible to plunge into the concrete calamity of the Loop feet first, dodging crowds and cabs to stare at Chicago’s magnificent buildings from the sidewalk. But the skyline takes on a surreal majesty as you float through its shadows on the Chicago River, and a river tour run by the Chicago Architecture Foundation is the best way to appreciate the finest collection of buildings in the United States.

8. Laugh till you can’t breathe at brilliantly improvised comedy

There are some biting, wickedly funny moments parading across Chicago’s improv comedy stages nightly, scenarios invented moments after a booze-fueled suggestion is hollered from the darkened hall. Audience participation is a key element, and the Second City theatre made Chicago comedy synonymous with spontaneous, often fairly raunchy laughs.

Since it’s one of Chicago’s signature nightlife experiences, seeing improvised comedy at Second City is one of the best ways to pass an evening.

9. A day at the beach

After the long, frigid winter, Chicagoans celebrate summer by hitting the miles of sandy beaches on the shores of Lake Michigan to spike volleyballs, splash around or spread a towel and soak up the summer sun. The stampede of joggers signals the start of the waterfront season when the weather starts to break in late April, and by the time the sweltering heat and sticky humidity of August peaks, making the water a dreamy 70°F (21°C), Chicago’s shoreline resembles Miami of the Midwest.

10. Shop ‘til you drop

Your poor, poor feet. Just when they thought you were done after spending the day tromping up and down the Magnificent Mile with an increasingly heavy bundle of packages, you discover that you’ve only seen the iceberg’s tip with respect to the wealth of shopping opportunities in Chicago. The Mag Mile sings the shoppers’ siren song as jingling cash registers accompany the age-old lyric: ‘cash or charge?’ The stretch of pavement on Michigan Ave in the Near North is stuffed silly with towering malls and high-end chains, such as Gucci, Louis Vuitton and Burberry. Things get festive around the winter holidays, with twinkling lights and plenty of window displays. But even though it may indeed be the most distinguished shopping area in town, it’s only the beginning.