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When it opened in 1927, The Hilton was the world’s largest hotel. Popular with many former US presidents, it oozes opulence, especially the Versailles-inspired Grand Ballroom. The Executive Class King Lakeview rooms offer the best views.

Palmer House has been an elegant fixture in the heart of the Loop for over 125 years. Extravagant frescoes decorate the ornate lobby’s ceiling, while the guest rooms are subtly elegant. The hotel even has its own upscale shopping arcade.

The Reliance Building – a handsome example of the Chicago School of architecture (see Skyscrapers) – was reborn as the boutique Hotel Burnham in 1999. Plush rooms are decorated in gold and blue; some offer great views.

In its heyday, this lavish hotel hosted stars such as Frank Sinatra and Liza Minelli. Comfortable rooms sport dark wood furniture and chintz furnishings; public areas are more impressive.

Enjoy the quiet elegance of this small, family-owned, European-style hotel. The Victorian parlor-like lobby and atmospheric Basil’s bar and café offer a chance to unwind, and the 149 guest rooms and suites are large and welcoming.

Originally a residential hotel, the Allerton Crowne has a high-ceilinged, 1940s-inspired lobby, and large, traditional guest rooms with marble baths and lots of amenities. Don’t miss the panorama from the 25th floor.

A quiet, understated European ambience has permeated this hotel since it opened in 1928. The 221 guest rooms combine elegant tradition with mod cons, and the Presidential Suite was a favorite of Katherine Hepburn. Check out the Molive restaurant with its menu of over 200 tantalizing martinis.

This former nurses’ residence, built in the 1920s, now aptly bills itself as a quaint little hotel with old-world charm. The general effect is light and spacious, though some of the rooms and furnishings are a little tired.

An inviting fireplace welcomes you at this 1920s-built hotel, where guest rooms are small but comfortable; some have antique furniture and four-posters. Mike Ditka’s restaurant is famous for its steaks and the collection of sports memorabilia.

This hotel, once owned by Playboy Magazine, has hosted guests as famous as John Kennedy and Al Capone. Its 1930s lobby hosts the Martini Bar, and the guest rooms exude a timeless elegance.