Get Swept Up in Shopping in the Windy City

Chicago offers a plethora of options for the consumer or browser

Among the many things that Ferris Bueller did in Chicago on his infamous Day Off, one thing he did not do was go shopping. But, if he did, there is no doubt he would not have had a hard time finding where to go.

And you should start at the beginning with the Marshall Field and Co. Building in downtown Chicago. Rebuilt after the Great Chicago Fire of 1871 and then rebuilt again after another fire, the current building has stood since 1906 and is the second-largest retail store in North America. Besides being a Macy’s now, the building is listed on the National Register of Historic Places and has been declared a National Historic Landmark, so it’s worth visiting if you are not shopping. It features some impressive architecture, which includes a mosaic vaulted ceiling designed by Louis Comfort Tiffany. The store was the first to offer a bridal registry and provide personal shopping assistants, have escalators in the stores and have a restaurant in a department store. That restaurant, the Walnut Room, remains open today and you can find it on the seventh floor, along with other eateries.

The Marshall Field and Co. Building is at 111 N. State Street in what is considered the Chicago Loop area of the city. Across the street, you will find Block 37, a five-story mall with a dine-in movie theater on the top level. Block 37, named after one of the original city blocks in the 1830s, features beauty and fashion retailers. But its real draw is its Latinicity Food Hall & Lounge, which spotlights award-winning chefs in a variety of restaurants.

Walking a couple of blocks south of Block 37 and Marshall Field’s, you might need some new shoes. But you’ll be in luck because along State Street you will find flagship stores for Footaction, DSW, Skechers, Vans and even Crocs. There is also a House of Hoops by Foot Locker.

If you are looking for high-end fashions or want to window shop, then head north to Oak Street since it’s cheaper than flying to Italy or France. Here you will find boutiques from designers such as Christian Louboutin, Armani, Prada, Hermes, as well as Tory Burch, Jimmy Choo, Vera Wang and Harry Winston.

Like most big cities, Chicago has plenty of flagship stores, but nowhere will you find them more concentrated than you will in the Magnificent Mile.

This stretch of Michigan Avenue in downtown Chicago boasts more than 450 retailers with three multilevel shopping centers.

Just three blocks south of Oak Street along Michigan Avenue is Water Tower Place, an eight-story mall inside a 74-story skyscraper. It is home to more than 100 retail stores, including a multilevel Macy’s and a flagship American Girl store as well as the Chicago Sports Museum and the Broadway In Chicago’s Broadway Playhouse so that you can add some entertainment or culture to your shopping. Water Tower Place was one of the nation’s first mixed-use developments as it also features a hotel and condominiums.

The Shops at North Bridge are another multilevel shopping center, this one, however, is also multiblock, with enclosed multilevel walkways that cross streets. There are more than 50 upscale retail locations, anchored by Nordstrom, and 20 restaurants, with something to suit everyone’s taste from Eddie V’s Prime Seafood to Shake Shack.

Heading north up Michigan Avenue about three blocks, you will come across Dylan’s Candy Bar, the best place to unleash your inner child and grab your favorite candy flavors and get your sugar rush. Nearly across the street is the Cubs Team Store, if you are shopping for a fan of the team.

If you keep heading north along Michigan Avenue, you will come across 900 North Michigan Shops, yet another multilevel mixed-used building that houses a retail center. With Bloomingdale’s as its anchor, it is sometimes referred to as the Bloomingdale Building. It is home to more than 70 upscale stores, including a two-story Gucci, Montblanc and Tesla, as well as a 22,000-square-foot dining hall with 15 different stations offering food and drinks.

The newest tenant on the Mag Mile will be the Starbucks Reserve Roastery Chicago, scheduled to open Nov. 15. It will be the largest Starbucks in the world in the former four-story Crate & Barrell space at North Michigan Avenue and Erie Street. The Roastery will include on-site roasting, tours, a full kitchen and offer drinks inspired by the city of Chicago, according to a news release.

But if you plan on visiting Chicago soon, you cannot miss the city’s largest open-air market, Christkindlmarket. Inspired by a Nuremberg, Germany, market that was founded in 1545, this market features iconic German items such as nutcrackers, cuckoo clocks and beer steins, as well as Christmas tree ornaments and handmade goods. Traditional German foods such as sausages, sauerkraut and potato pancakes are dished up and the drink flows freely. It runs from Nov. 15 through Dec. 24 this year.

And to get in the holiday spirit even more, why not take in some holiday classics as a break from shopping? The Goodman Theatre’s annual holiday production of the Charles Dickens classic, “A Christmas Carol,” will be performed for its 42nd year from Nov. 16-Dec. 29. You also can ring in the holiday cheer with the Music Box Christmas Show, with a sing-a-long and double feature of “White Christmas” and “It’s a Wonderful Life” from Dec. 12-24.

Learn about the AAA Ohio travel offering and contact an agent to book your next destination today.

John T. Garcia is the Managing Editor of AAA Magazine.