Chicago

Across the Chicago River, immediately due North of the Loop, is a neighbourhood of densely packed galleries, with its requisite arts fairs and gallery walks. Wander around boutiques and speciality shops, including upscale antique stores and furniture dealers. It is a food lover’s paradise, with an amazing assortment of dining options to satisfy every palate and budget. After dark, young and hip club-goers descend on River North for its plentiful and vibrant nightlife.

Running the length of Michigan Avenue, from the Chicago River to Lake Shore Drive, the ‘Mag Mile’ is the heart of the city’s shopping district. Here, upscale brand named stores stand alongside historic hotels and landmarks. Such as the Water Tower and Pumping Station – one of the few structures left standing after the Great Chicago Fire of 1871. It is an ideal place to stay and shop, and a great base to explore from.

The central business district, nicknamed because of the elevated ‘El’ train tracks that loop around the city centre. Amid the skyscrapers and office buildings is the city’s famed Theatre District comprising the Cadillac Palace Theatre, Ford Centre for the Performing Arts Oriental Theatre, Bank of America Theatre and the Chicago Theatre, whose glittering marquee is one of the city’s most recognisable icons.

Aptly named, this is one of Chicago’s most affluent neighbourhoods, where new mansions continue to spring up alongside the grand residences built by Chicago’s 19th century elite. Once home to hotel-magnate Potter Palmer’s castle-like mansion, it now includes the Astor Street Historical District’s beautiful brownstones, the architectural riches are boundless. The Rush & Division intersection, a few blocks away, is a vibrant hotspot of trendy bars and nightclubs – the perfect place for people watching and celebrity spotting.

A neighbourhood of luxurious high-rise apartment buildings, internationally renowned restaurants, popular attractions like Navy Pier and the John Hancock Observatory, and the world-famous Magnificent Mile shopping district along Michigan Avenue. Its legendary origins, however, involve a colourful eccentric, George Wellington ‘Cap’ Streeter, who laid claim to this patch of prime lakefront land around his shipwrecked schooner, and numerous gunfights with police and court battles that led to his eventual eviction.