Chicago’s architectural story began before modernism — this Venetian Gothic landmark, previously a private club for the city’s (male) movers and shakers, dates back to the final decade of the 19th century. It’s not just any old building, but a beautiful old building, and it doesn’t hurt that you’re looking straight out over Millennium Park. But there’s plenty worth looking at indoors as well — and an extravagant food and drink program that draws locals and guests alike.

New York certainly has its architectural charms, but only in Chicago can a hotelier reasonably hope to set up shop in a masterwork like the 1929 Art Deco Carbide & Carbon Building, with its stately dark stone and immaculate gold trim. It’s a perfect fit for Pendry, the urban luxury-boutique cousin to the Montage resorts. Beds come dressed in Fili D’Oro linens, bathrooms clad in marble with custom-made bath products, and rooms come supplied with modern necessities.

A remarkably complete package: contemporary design, state-of-the-art comforts, thoughtful, professional service, and a link to the city’s urban history, embodied in its location: 330 North Wabash, formerly known as IBM Plaza, the last work of the modernist master architect Ludwig Mies Van der Rohe. The Chuan Spa is an elaborate one, complete with pool and fitness center. Meanwhile, Travelle is the restaurant, bar and lounge with Mediterranean-inflected fare.

In the middle of Chicago’s Magnificent Mile of department stores and designer boutiques is the Peninsula Hotel, only the third in America. The lobby is spacious and grand, located five floors up, above a retail concourse. Rooms are elegant as well, while Shanghai Terrace is true to its name, offering outdoor seating with a view of the Miracle Mile.

The Gwen doesn’t just echo the aesthetics of Twenties and Thirties Chicago, it’s an authentic piece of history — its façade comes from the 1929 McGraw-Hill building, and it’s named for the sculptor Gwen Lux, whose work still adorns it today. Inside it’s a thoroughly contemporary boutique-style luxury hotel, with Art Deco accents and 21st-century comforts. There’s an open-air rooftop bar and a weekend “Tipsy Tea” served in the hotel’s lounge.

One look at the huge English courtyard, or the museum-like marble lobby, and it’s clear that this is a full-scale luxury hotel all the way — especially since all this black, white, and polish gives off a dazzling Art Deco vibe. Fortunately the hotel undercuts its potentially chilly elegance with outstanding service, for which no staff person is allowed to accept a tip.

The Viceroy hotels exist at the intersection of luxury-hotel extravagance and boutique-hotel tastefulness, and the Viceroy Chicago is no different. The building, a gently undulating glass tower, is pure luxe modernity, but the lower floors blend effortlessly into Chicago’s Gold Coast, thanks to the meticulously preserved façade of the 1920s-vintage Cedar Hotel, which was reassembled brick by brick once the tower was complete.