Chicago's Chic Shopping Destination Is An Affluent Lakeside Neighborhood With Skyline Vistas

Online shopping may be efficient, but it rarely captures the pleasure of browsing in person. Hitting up the designer stores and cafes at South Coast Plaza in Costa Mesa, California, known as one of the five biggest malls in America, or browsing the shops and sculptures at NorthPark Center in Dallas, Texas deliver on both retail options and ambiance. Another destination that blends shopping with sightseeing is Chicago's Streeterville neighborhood, a retail hub anchored by Michigan Avenue's famed Magnificent Mile, a 13-block promenade stretching from the Chicago River to Oak Street. Overlooking Lake Michigan and offering landmarks like Navy Pier and the Museum of Contemporary Art, the area offers easy access to flagship stores, shopping centers, and skyline views — all within walking distance.

Streeterville boasts an impressive skyline comprised of luxury high-rises with upscale amenities for permanent residents. Located in the 100-story tower formerly known as the John Hancock Center, 175 E. Delaware Place offers upmarket condominiums across 49 floors. While visitors may not have access to the tower's residential living spaces, the 94th floor houses 360 Chicago. This observation deck features sweeping views over downtown and Lake Michigan, along with a cocktail lounge, CloudBar. If that feels too dizzying, another option is Park Tower, a 70-story high-rise with condos built above the Park Hyatt Hotel. The hotel offers rooftop dining and an open-air terrace on the seventh floor at NoMI while overlooking the city. 

These towering structures are a long way — literally — from Streeterville's humble beginnings as a landfill. As the story goes, Captain George Streeter ran his steamboat into a sandbar off Lake Michigan's coast in 1886. Refusing to leave, he staked a claim to about 180 acres in the area and developed it into a shantytown with a red light district, calling himself mayor of the "District of Lake Michigan." Lawsuits and court battles ensued between the squatter and Chicago for nearly four decades until he was evicted. In the meantime, his namesake prime piece of real estate experienced two economic booms — once in the 1920s when the Michigan Avenue Bridge opened across the Chicago River and again after World War II with the introduction of the Magnificent Mile.

Today, Streeterville and the Magnificent Mile are major shopping destinations, particularly during the holiday season, when storefronts and streetscapes are decorated with lights and seasonal displays. One of its central shopping spots is The Shops at North Bridge. This airy, four-level structure is filled with about 50 mid-range and upscale retailers, including Nordstrom, MCM Worldwide, and MAC Cosmetics, and specialty stores such as Aesop and Room & Board. The center also houses the 63,000-square-foot Eataly marketplace and dining complex, featuring eateries, a panini counter, a Nutella bar, a wine shop, and two coffee bars.

Fans of Kate Spade, Gucci, and Max Mara will want to take the 10-minute walk to 900 North Michigan Shops, featuring more than 60 premium brands. Reviews on Google note the "polished atmosphere" of the mall and its atrium ceiling's digital art installation, housed on the first seven floors of a 67-story building. Its food emporium, Aster Hall, offers burgers, sushi, tacos, and ramen, with a stylish sixth-floor bar and study filled with lounge chairs, couches, and high-tops with brass accents. The Four Seasons Hotel is also located in the skyscraper, where rooms can start at $445 a night. (You also won't be far from the action if you stay at the InterContinental Chicago Magnificent Mile, home to one of America's largest indoor swimming pools. )

If you want to skip the malls, the avenue is lined with high-end retailers, such as Saks Fifth Avenue, Neiman Marcus, Burberry, and Louis Vuitton. In between perusing, take a break at the Starbucks Reserve Roastery, the world's largest Starbucks with five floors dedicated to an elevated coffee experience for coffee flights, coffee-infused cocktails, and guided tours of the roasting process. Redditors say brace yourself for a wait. For more diverse neighborhood shopping in Chicago, plan a stop in the nearby Southport Corridor.