You don’t have to be a CEO of a Fortune 500 company to live the high life in Chicago—although being in that higher tax bracket certainly doesn’t hurt. Whether you’ve saved up for that one big splurge or are accustomed to (and comfortable with) dropping hundreds on a food and bar tab, Chicago presents a bounty of options for where to stay, play and throw your Benjamins around like dollar bills. In neighborhoods like the Gold Coast, you’ll stumble upon luxury boutique after luxury boutique, and have plenty of time to stop for a Belvedere martini along the way. There isn’t an opulent hotel or fancy steakhouse too far from these parts, or potentially a celebrity sighting.
Based on or near the Mag Mile? The grande dame of boulevards in Chicago also doubles as a retail mecca. With brands like Bloomingdales, Neiman Marcus, Saks Fifth Avenue, Burberry, Cartier and Tiffany within blocks of each other, Michigan Avenue tempts from its northernmost tip—Oak Street—all the way down to its southern gateway, where the iconic Wrigley Building and the historic Tribune Tower face each other. At the end of your day, you can certainly reward yourself with Champagne and caviar, or as the locals do—with swine and wine at the Purple Pig. Enjoy these luxury experiences in Chicago.