Its architectural greatness isn't just in skyscrapers but in atmospheric restaurants and a multitude of extraordinary hotels. Blair Kamin names old and new favorites

That toddlin' town has learned to toddle in new ways, a trend revealed in Chicago's astonishingly diverse hotels and restaurants. My recommendations, I should confess, bespeak an architecture critic's sensibility. When it comes to dining, I am concerned with the flavor of both the place and the food. So I don't dwell on well-known haute cuisine kitchens such as Charlie Trotter's. Similarly with lodgings, my preference is for hotels that are visually distinctive rather than generic.

The best, and most beautiful, way to get the feel of the city is to take the Chicago Architecture Foundation's 90-minute boat tour along the Chicago River, where you glide past an array of dazzling skyscrapers—sometimes, unfortunately, with loud guides who never shut up (312-922-3432; architecture.org; $26–$28 per person). An enormous variety of walking tours also set out from the foundation's headquarters at 224 South Michigan. The Historic Skyscrapers walk, for instance, charts the innovations of structures ranging from the Rookery Building, with its ethereal light court, to the Chicago Board of Trade Building, which has a knockout refurbished Art Deco lobby.

The Frank Lloyd Wright Preservation Trust's tours are a must for Wright fans (708-848-1976; wrightplus.org; $12 each). You can combine a tour of his Robie House with a visit to the lone surviving major building from the World's Columbian Exposition of 1893, the Museum of Science and Industry (773-684-1414; msichicago.org), and the University of Chicago's campus, which has the serenity of neo-Gothic quadrangles as well as bracing contemporary buildings by such architects as Cesar Pelli, Ricardo Legorreta, and Rafael Viñoly.

Millennium Park often has events, including free tours at 11:30 and 1 daily (312-742-1168; millenniumpark.org), and those with a taste for modern architecture and design should visit the campus of the Illinois Institute of Technology (IIT). Located at 33rd and State, it was planned and designed by Ludwig Mies van der Rohe and has buildings by Rem Koolhaas and Helmut Jahn. Tours of both are available (312-567-3077; mies.iit.edu/tours; $5).

Prices quoted are for August 2007.

Lodging
Chicago's true bastions of luxury are in mixed-use high-rises around North Michigan Avenue (where you should request an east-facing upper-floor room for views of both the city and the lake). Premier among these are three Condé Nast Traveler Gold List hotels: The Peninsula, with grand-scale, Asia-meets-Deco public rooms (312-337-2888; chicago.peninsula.com; doubles, $525–$650); the Four Seasons, with sumptuous European-style amenities such as a Roman pool with a glass-dome ceiling (312-280-8800; fourseasons.com; doubles, $495–$710); and the more contemporary but not austere Park Hyatt, the flagship of the local Pritzker family's hotel empire (312-335-1234; parkchicago.hyatt.com; doubles, $375–$545).