When it comes to holiday magic and creating memories of a lifetime, why not head down to Chicago's Magnificent Mile and start a mother-daughter* shopping weekend?

Spanning Michigan Avenue between the Chicago River and Oak Street, The Magnificent Mile features some of the most prestigious shopping the Windy City has to offer. Home to the John Hancock Center, the Wrigley Building, Tribune Tower, Chicago Water Tower, and the historic Allerton Hotel, the district really "comes to life," this time of year.

Before you plan your trip, make sure and consult the official website for The Magnificent Mile. The site highlights seasonal events as well as maps and travel tools (including a guide to parking, which often comes with a big city price tag). Had we planned ahead, we would have known our visit coincided with the BMO Harris Bank Magnificent Mile Lights Festival featuring a parade, fireworks, horse-drawn carriages and some of the most impressive crowds the stores enjoy all year.

With all girls in our group, we focused on chocolate and shopping with a "surprise" dinner at the American Girl Place Cafe. To begin, enjoy a gourmet cupcake at Sprinkles Cupcakes on 50 East Walton Street. If you can snag a seat at the deli-style counter, savor your dessert while you partake in a little people watching.

If milk chocolate is more your style, head to Hershey's Chocolate World (822 North Michigan Avenue) and behold the world's largest Chocolate Bar. You can also make a custom wrapper on a 7-ounce milk chocolate bar—complete with souvenir photo.

With shops and stores lining both sides of the street, North Michigan Avenue retail cornerstones include 900 North Michigan Shops (the enormous Christmas tree near Bloomingdale's is a perfect Christmas Card backdrop) and Water Tower Place, which is home to American Girl Place Chicago.

Spanning two levels, American Girl Place (835 North Michigan Avenue) is a "must see" destination for any child who owns an American Girl doll, Bitty Baby, or Bitty Twins. Offering traditional shopping, a doll hair salon, photo studio, and cafe, it's hard to miss the trademark red American Girl shopping bags peppered among the shoppers.

Decorated "to the nines," in a holiday theme, dining at the American Girl Place Cafe is all about the experience. Dolls are welcome to participate (loaner dolls are available so no child is without a special friend) and advanced reservations are required (menus, prices, times and a link to making an online reservation are available here).

If you are looking for four-star dining in Chicago, American Girl Place Cafe is not for you. That said, the ambiance, service, and "little details" make the experience. The menu is also quite child friendly, with options for parents to order a glass of wine and more adult entrees (salmon, for example). We absolutely adored the dessert plate.

If your visit includes an overnight stay, consider making a reservation at the Radisson Blu Aqua Hotel near Millennium Park (221 North Columbus Drive, to be exact). Centrally located and offering views of Lake Michigan, downtown, and the park, room rates start at $139/night. Between the eclectic lobby and ultra-modern rooms, the hotel features an indoor and outdoor (seasonal) swimming pools. The Radisson Blu Aqua is also pet friendly and offers competitive daily underground parking rates.

If you make a reservation to stay at the Radisson Blu Aqua Hotel, consider an upgrade to Business Class. The extra cost includes access to both the evening reception and the continental breakfast in The Lounge on the 17th floor, as well as the use of an iPad in your room and an additional 1,000 Gold Points per night. With beer, wine, and one of the more delicious continental breakfasts we've enjoyed in a long time, families will enjoy the view as well as the comfortable space to unwind after a long day of shopping, dining and memory making.

* Of course, sons make for a great substitution! We happened to grab our girls this year, but the boys are on deck for 2014. A special thanks to American Girl Place for complimentary dining at the American Girl Cafe as well as Radisson Blu Hotel for one night's lodging accommodations and an upgrade to the fabulous Business Class lounge.