During the Roaring Twenties, the Allerton was one of the first highrises to pop up on the Chicago skyline. Now a designated landmark, the Michigan Avenue hotel retains some classic elements (such as its exterior sign that reads “Tip Top Tap”—the name of the popular cocktail lounge that closed in 1961) while adding some contemporary accents. The hotel had a makeover in May 2008 and the rooms are in tip-top shape: The sophisticated spaces are done up in traditional navy blue and white, while modern touches, such as trendy patterned throw pillows, white upholstered headboards and iPod docking stations, are sprinkled throughout. Beware of the rooms labeled “Classic”—that’s code for “tiny.”

The Allerton Hotel - Michigan Avenue Amenities:

• 443 rooms. High-speed Internet access. Restaurant, bar. Fitness center. Business center.