Chicago

Chicago's beloved front garden — Millennium Park, home to 'Cloud Gate' (the mirror-polished, bean-shaped sculpture everyone calls 'The Bean'), the dramatic Pritzker Pavilion, the Crown Fountain's giant face-projecting towers and the lush Lurie Garden. Snap your reflection in The Bean, cool off in the fountain, and enjoy a free summer concert; it's the city's joyful, free civic heart and its most iconic photo. A wonderful, lively spot right downtown by the lake. Absolutely unmissable, day or night.

The single best thing to do in Chicago — a boat cruise along the Chicago River, gliding between the soaring skyscrapers as an expert guide tells the story of the city that invented them, from historic gems to gleaming modern towers. It's the perfect, jaw-dropping introduction to the city's world-famous architecture, seen from the water where it looks its most spectacular. Go on a clear day or at golden hour; it's informative, relaxing and unforgettable. A must-do highlight and the definitive Chicago experience. Book ahead in summer.

One of the world's great art museums — the Art Institute, guarded by its famous bronze lions, with a stunning collection spanning Monet's haystacks and a room full of Impressionists, Grant Wood's 'American Gothic', Hopper's 'Nighthawks', Seurat's pointillist masterpiece and superb modern and ancient art. World-class and vast, it rewards hours of wandering; don't miss the Impressionist and American galleries. A cultural highlight of the city and the country, right on Millennium Park. Unmissable for any art lover. Give it half a day.

Ride to the 103rd floor of the Willis Tower (the old Sears Tower, once the world's tallest) for the Skydeck — a breathtaking panorama over the entire city, the lake and, on a clear day, three neighbouring states. For a thrill, step out onto 'The Ledge', a glass box jutting from the building with nothing but air (and 412 metres) beneath your feet. Dizzying and unforgettable; go at sunset for the city lights. A classic Chicago experience and a spectacular overview. Book timed tickets to skip the queue.

Chicago's most famous food — deep-dish pizza, a glorious, buttery-crusted, pie-like creation loaded with cheese, chunky tomato sauce and toppings, so thick you eat it with a knife and fork. Debate the best spot (Lou Malnati's, Pequod's, Giordano's), order one to share (it's enormous and rich), and settle in for a proper Chicago feast. Whatever you think of the deep-dish debate, it's an essential, only-in-Chicago experience; the city also does a superb thin-crust 'tavern style'. A delicious, iconic must. Come hungry.

Chicago's grand shopping boulevard — the Magnificent Mile, a stretch of Michigan Avenue lined with flagship stores, department stores, hotels and landmarks like the historic Water Tower (a survivor of the Great Fire) and the Wrigley Building. Stroll the bustling avenue, shop or window-shop, admire the architecture, and cross the river for the skyline views. Even if you're not buying, it's a lively, grand promenade at the heart of the city; especially pretty lit up at night and at Christmas. A classic Chicago wander.

Chicago's glorious lakefront is its greatest asset — a continuous 30-km trail of parks, harbours and sandy beaches running along Lake Michigan, with the skyline on one side and the endless blue lake on the other. Walk, cycle or run the path, hit a city beach (North Avenue and Oak Street are central) for a summer swim, or just admire the skyline from the water's edge. Free, beautiful and quintessentially Chicago, especially glorious in summer; rent a bike for the full sweep. A wonderful, healthy highlight.

One of the world's great natural-history museums — the Field Museum, on the lakefront Museum Campus, famous for 'Sue', the largest and most complete Tyrannosaurus rex ever found, plus vast halls of dinosaurs, ancient Egypt (with real mummies), gems, cultures and wildlife. Grand, sprawling and superb for all ages, it's a highlight of the city's cluster of lakefront museums (alongside the Shedd Aquarium and Adler Planetarium). A wonderful, immersive few hours, especially with kids. An excellent cultural stop by the lake.

On the lakefront Museum Campus, the Shedd Aquarium is one of the best in the world — home to beluga whales, dolphins, sea otters, sharks, a huge Caribbean reef tank and an Amazon rainforest exhibit, all with a stunning backdrop of the skyline and lake through its grand windows. Engaging and beautiful, it's a great outing for families and anyone who loves marine life, and pairs perfectly with the neighbouring Field Museum and Adler Planetarium. A delightful few hours on the lake. Book timed tickets ahead in summer.

Chicago is the birthplace of modern improv comedy, and there's no better place to laugh than The Second City — the legendary Old Town theatre where Bill Murray, Tina Fey, Steve Carell and countless other stars got their start. Catch a sharp, hilarious sketch-and-improv revue in the intimate club, and see comedy history in the making. It's a quintessential, only-in-Chicago night out and a joyous evening of laughs. Book ahead for the main-stage shows; a brilliant, uniquely Chicago experience. Great fun.

Two of Chicago's loveliest historic neighbourhoods — Old Town, with its charming tree-lined streets of Victorian townhouses, cafés and the famous comedy clubs, and the elegant Gold Coast, all grand mansions and leafy avenues near the lake. Wander the pretty, atmospheric streets (they survived the Great Fire), admire the architecture, and enjoy the cafés and boutiques; it's a graceful, relaxed contrast to the downtown towers. A delightful area to stroll, especially on a fine day. A charming, genteel wander near the centre.

Chicago's hippest neighbourhood — Wicker Park and Bucktown, a buzzing tangle of indie boutiques, vintage and record stores, street art, third-wave coffee shops, craft-beer bars and some of the city's best restaurants and live music. Wander the creative streets, browse the shops, and settle into a cool bar or café; it's the perfect place to feel young, arty Chicago beyond the downtown sights. A great afternoon and evening of shopping, eating and people-watching. The heart of the city's hip side; cool and lively.

Chicago is the home of electric blues and a jazz powerhouse, and hearing live music in a smoky club is essential — catch a raw, soulful set at a legendary blues joint like Buddy Guy's Legends or Kingston Mines, or cool jazz in a Green Mill-style lounge (a former Al Capone haunt). The music is world-class, the atmosphere intimate and electric, and it's woven into the city's very soul. A quintessential, only-in-Chicago night out for any music lover. Soulful, historic and unforgettable. Don't miss it.

In summer, Chicago becomes a beach city — Lake Michigan's sandy shores fringe the whole lakefront, with popular central beaches like North Avenue Beach and Oak Street Beach offering sand, swimming, volleyball, kayaking and a buzzing scene, all with the skyline as a backdrop. Swim, sunbathe or grab a drink at a beachfront bar; it's a surprising, delightful slice of summer right in the city. Free and quintessentially Chicago in the warm months. A wonderful, only-in-summer highlight. Best June to September.

Beyond deep-dish, Chicago is a serious food city with a gloriously diverse neighbourhood scene — the Chicago-style hot dog (never with ketchup) and Italian beef sandwich, plus superb Mexican food in Pilsen, Polish in the north-west, and celebrated fine dining and hip eateries in Logan Square, West Loop and beyond. Graze the neighbourhoods, try a classic dog and an Italian beef, and book a buzzy dinner; the quality, variety and value are outstanding. A delicious way to explore the real city. Come hungry and adventurous.