Top Luxury Experiences in Chicago

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.


With three distinct experiences (kitchen table, first floor gallery and three second-floor salons), patrons get to choose what kind of culinary adventure they want to embark upon. Reservations required. D (daily).

Spa at Trump

Talk about an elite treat: Boasting 12 treatment rooms, many with floor-to-ceiling downtown views, one with his-and-her massage tables and massive soaking tubs, the 23,000-square-foot Spa at Trump takes wellness to a new level of luxury.


Inspired by the variety of seasonal American cuisine, this chic resto highlights inventive dishes from Chef Ricardo Jarquin. There’s no doubt that Mies van der Rohe—who designed the building—would have approved of the minimalist, mid-century modern interior, featuring a glass-enclosed kitchen.

Three Dots and a Dash

A discreet location down an alley in River North just makes the reward all the sweeter: fresh tiki cocktails served in the most curious of barware, from conch shells to ceramic pineapples. The Polynesian touches are as sugary as the cocktails.

Gold Coast

One of the most affluent neighborhoods in the nation, the Gold Coast lends itself to leisurely walks along tree-lined streets; one of the most noteworthy is Astor Street, populated with opulent, historically significant mansions.

The Aviary

Adjacent to Next, this cocktail lounge by Grant Achatz boasts a lush vibe, delicious bites and an innovative drink menu—standouts include the Blueberry and the Popcorn. You’ll also find classics like sidecars, martinis and daiquiris.