Chicago's Michigan Avenue at Christmas. Credit: smaedli.

By Vince Font

One of the best holiday vacations in memory was the time I took my daughters Christmas shopping in Chicago at  American Girl Store on the Magnificent Mile. Not only did we stay at one of the finest Chicago hotels and shop some of city’s most incredible stores, this dad got to share in a uniquely “girl experience” with two of the most special ladies in his life. So what if I broke the bank a bit on clothes and tea for dolls? To my girls, I was a rockstar dad with a new appreciation for dolls (just don’t tell my poker buddies).

The fact is, I’ve always had trouble Christmas shopping. These days with everything just a mouse click away, it should be easy enough to find what you need — but too much choice can scramble the brain. So it was a stroke of genius to decide to take my girls straight to the source (and their own version of heaven) to let them choose their own Christmas gifts.

But first, lodgings. Having never been to the Windy City, I performed meticulous research to find the best Chicago hotels. Here are my top picks for any Chicago vacation, and especially for those looking to shop till they drop.

  • The Drake Hotel, located just north of American Girl and around the corner, was closer to our destination and offered far lower rates than almost all of the other hotels on North Michigan Avenue proper. This is where we stayed  and I don’t regret it; it’s positively loaded with historic charm (and that’s saying something in a city as rich with history as Chi-town), and the lower level shopping area even managed to elicit comments of approval from my junior travel partners. And did I mention our afternoon tea party at the Palm Court? The girls enjoyed fancy French pastries and cookies while I soaked in the history of an event enjoyed by royalty in this very same room for decades.
  • Chicago’s Essex Inn had the best nightly rates by far, but its location on South Michigan Avenue was the determining factor that led me to pass. That, and I didn’t want to have to hear the girls admonish me the whole way for not picking a place immediately adjacent to American Girl. Sometimes fatherhood can be brutal.
  • The Marriott Downtown and Omni Hotel were both asking rates a tad too steep for not being directly on top of the American Girl Place. Although having taken in the majestic city skyline views offered at these two glamorous Chicago hotels, I’ve vowed to try them both the next time I’m in town with a few too many dollars in my wallet.
  • The Allerton Hotel was my second choice, both for its location and cost, but at the risk of spending too much time hemming and hawing, I let the decision rest on a coin toss. I’d certainly recommend it as a viable location for someone looking for great Chicago hotel deals.

In the end, the vacation was a triumph. The only thing I have to face now is having to field suggestions from my merry band of travelers as to when we’ll be going back. If you’ve got girls and are interested in drawing up a list of potential Christmas vacations, you could do a whole lot worse. Make sure to do what I did and book your flight and hotel together to save even bigger.

Vince Font is a freelance writer born in Puerto Rico and currently escaped to Utah. When not dreaming of interstellar travel, he’s on the hunt for weird, wacky, and off-the-beaten-track vacation destinations. Next stop: The Lizzie Borden Bed and Breakfast.


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Tagged: Chicago Vacation, Holidays & Events, Hotels


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