Master the Mile

When it comes to the world’s great thoroughfares, Chicago’s Magnificent Mile goes toe-to-toe with New York’s Fifth Avenue or the Champs-Élysées in Paris. A wide, flower-filled boulevard bounded by the Chicago River on the south and Oak Street to the north, the Mag Mile constantly bustles with crowds of locals and visitors alike.

The Mag Mile’s heart and soul is the Historic Water Tower, a striking limestone structure at Michigan and Chicago avenues. As one of the few buildings to survive the Great Chicago Fire of 1871, the Historic Water Tower and its partner Pumping Station across the street symbolize the city’s resiliency as well as its flair for the dramatic. The Historic Water Tower is now home to the City Gallery, which features a rotating display of works by local artists. The Pumping Station houses Lookingglass Theatre Company, a hotbed of cutting-edge works founded by graduates of Northwestern University (including Friends alum David Schwimmer).

You’ve certainly found the right place if shopping is your bag. Start at The Shops at North Bridge, a collection of upscale stores and restaurants that serves as the base of North Michigan Avenue. Here you’ll find one of the country’s largest Nordstrom stores, as well as chic shops like Hugo Boss, Swarovski and Vosges Haut-Chocolat, all in an ultramodern, mega-mall setting.

Stroll north along the avenue to Water Tower Place, an eight-floor retail mecca that was one of the first vertical malls in the world. Stores such as Macy’s, Henri Bendel and the flagship American Girl Place join Broadway Playhouse and eateries that include the baseball-themed Harry Caray’s 7th Inning Stretch (which features the Chicago Sports Museum).

On the north end of the Magnificent Mile lies the 900 North Michigan Shops, where more than 70 luxury retailers such as Gucci, Michael Kors and Bloomingdale’s combined with diverse dining options create a retail retreat where you’ll want to stay all day.

The Magnificent Mile isn’t just the place to flex your credit cards; it also offers one of Chicago’s richest concentrations of attractions. Want to tell some tall tales about your trip? Take the epic elevator ride up to 360 Chicago at the John Hancock Center, a breathtaking observation deck suspended 94 stories in the sky.

Art aficionados will be drawn to the Museum of Contemporary Art, a sleek and serene structure just removed from the hum of Michigan Avenue. Exhibitions here showcase works by important current artists from around the world.

With your shopping and cultural wish lists checked, indulge the other senses. For a caffeine boost, visit the recently opened Starbucks Reserve Roastery for all your caffeine-related needs. This five-story shrine to coffee also features a full kitchen/bakery and mixologist-crafted beverages. Pop into The Purple Pig, but get there early; the snug space draws crowds for its Spanish-inflected small plates (and rock ’n’ roll soundtrack).

Lunch like a celeb (and quite possibly with one) at RL, the Ralph Lauren restaurant that is as fashionable as its founder. To fully dine like a celebrity, book a table at Michael Jordan's Steak House for decadent steaks, cocktails, and steakhouse sides like roasted garlic mashed potatoes. 

Drink in gorgeous views at The dec Rooftop Lounge + Bar at The Ritz-Carlton Chicago, a swanky cocktail spot 12 stories above the Mag Mile. Or spice up your night with a taste of the exotic at Shanghai Terrace, one of the city’s top Chinese restaurants and rooftop lounges on the fourth floor of The Peninsula Chicago, named one of the top 5 hotels in the country.