Explore by theme
Not sure which neighborhood yet? Start with what moves you — a Gilded Age survivor, a Jazz Age tower, a bank-vault lobby, a rooftop perch, or a budget gem with real soul. Every one is a boutique or landmark hotel in a building worth the trip, grouped here by era and character.
Ghost-tour legends, presidential intrigue, and Prohibition-era lore across six of Chicago's most storied addresses.
6 hotels →
Grand hotels and private clubs born in Chicago's turn-of-the-century boom — the oldest stays in the guide, dating to 1910 and before.
15 hotels →
Terra-cotta, gold leaf and Roaring-Twenties glamour: the dazzling towers of the 1910s–'30s, reborn as hotels.
34 hotels →
Office blocks, athletic clubs, banks and commercial landmarks given a second life as places to stay.
15 hotels →
Hotels crowned with a rooftop bar, restaurant or pool — the best seats above the city.
13 hotels →
Characterful, design-forward stays and hostels that keep the history and drop the price — real value in authentic Chicago historic buildings.
11 hotels →