Chicago Architecture 101

The tallest building in the United States, the Sears Tower, stands over the city skyline with its two white, modern-looking antennae, and scans the city like a great, square sentinel. The heights reached by this building were made possible thanks to decades of architectural evolution, which was, in turn, made possible by architects, engineers, and the workers who powered Chicago’s drive to reach the sky.

Sports in Chicago is a really big deal year round, but during football season—college and pro—there’s nothing better than viewing a big game with a few hundred people who share your same enthusiasm. You’ll want to catch all the action at:

Make a reservation at one of these business-friendly restaurants and score some points. Added bonus: they all have private dining options if you need to accommodate a larger group.

Hester, the Chicago Bears’ speedy return man, is back just month’s off his record-breaking first season (accolades include the first ever opening-kickoff return for a touchdown in a Super Bowl and the maxium 100 rating for speed in the latest version of Madden). Despite his busy schedule, Hester found time to sit down with Concierge Preferred to chat about his ideal day in his new hometown.

The autumn look exudes confidence and beauty. Chicago’s choicest boutiques offer up the latest in luxury, from the perfect tailored ensemble to delicate, detailed separates. With our fall fashion forecast, your new heels will be hitting the sidewalk of the Magnificent Mile before the first golden maple leaf.

We work with hundreds of Chicago concierge for a reason: They know what they’re doing! Our researchers in the field are always on the job, be their work in the city or the suburbs, so here we look at must-hit spots in some of our concierges’ favorite neighborhoods.

Chicago’s rich, live-music scene goes far beyond hearing updated versions of “Sweet Home, Chicago,” “My Kind of Town” or “Take Me Out to the Ballgame” at the local pub. You’re likely to find your favorite sounds all over town, and at these particular venues you can sometimes join in on the action!

From foliage to football to festivals and events, Chicago is the place to be as summer temperatures wane.

Here's a look at some of offerings Trump has in store.