Chicago: Where to Stay: Overview

Chicago’s top hotels, the Peninsula, Ritz-Carlton, Park Hyatt and Four Seasons, are situated a few blocks from each other, with prime access to the shopping on the Magnificent Mile. Those who like a sleek, modern look will appreciate the Peninsula and the Park Hyatt; the Ritz-Carlton and Four Seasons are more traditional. Traveling with kids? You’re in luck: click here to read about the outstanding local options.

Tip: Even in the off-season, it’s imperative to reserve at Chicago hotels well in advance, as the city hosts many conventions. During October and May, the busiest months, it’s not unheard of for all 20,000 of the city’s hotel rooms to be booked. “We’ve actually gotten to the point where visitors end up having to stay in Indiana,” one hotel manager told me. Also note that room taxes are a steep 14.9 percent.