The Drake

The Drake has anchored the top of Michigan Avenue since New Year's Eve 1920, an Italian Renaissance palazzo by Marshall & Fox set where the Magnificent Mile bends to meet Lake Michigan and Oak Street Beach. Its rooftop sign is a fixture of the skyline, its guest book runs from Winston Churchill and Walt Disney to Queen Elizabeth II and Princess Diana, and for generations of Chicagoans the hotel has been the default setting for engagements, anniversaries and Christmas gatherings.

The heart of the building is the Palm Court, a fountain-centred lobby lounge where afternoon tea has been served with full ceremony for a century, and the Coq d'Or bar, which poured its first drink the day after Prohibition ended in 1933 and still trades in dark wood, red leather and generous measures. Guest rooms above are traditional in dress—floral fabrics, classic furniture—and the best of them look straight up the lakefront, a view no newer tower on the Mile can quite reproduce.

The Drake is not the city's most polished luxury product; younger hotels out-spa and out-design it, and its scale keeps it busy with events. What it offers instead is authenticity: a working piece of Chicago history in the single best position on the Gold Coast, steps from Oak Street's boutiques and the lakefront trail. For travellers who value patina over minimalism, it remains an affectionate first choice.