Christmas Magic Amidst Chicago's Magnificent Mile

Christmas Magic Amidst Chicago's Magnificent Mile

“City sidewalks busy sidewalks
Dressed in holiday style
In the air
There’s a feeling
of Christmas…”

Ahh Christmas in the city.

A couple years back I had the displeasure of finding myself in New York City, or more specifically Rockefeller Center, amidst the holiday season. After an afternoon of getting jounced around and consistently stuck in people traffic jams, I retired in the Scroogiest of moods and feeling the pain of driven cattle all over the US.

Chicago Christmas Trolley

Since that experience I have never failed to appreciate the joy of Christmastime in my home city of Chicago. Home to far less people (and far less garbage) than NYC, over the years I have found the holidays in Chicago to be downright delightful.

Chicago already has much to offer, and the list of clean & safe neighborhoods that like to get festive for the holidays is expanding every year. Still, one of the most classic areas for a Christmas outing has to be Chicago’s Magnificent Mile.

Starting just north of Water Tower Place on Michigan Avenue, the Magnificent Mile is officially considered to run only as far south as the river.

Personally, I like to start a holiday visit to the Mag Mile at Millennium Park, which is just a few blocks south of the river. It includes not only the classic oval-shaped ice skating rink, perfectly positioned in the front of Millennium Park with Michigan Avenue’s historic skyscrapers as a backdrop, but also the newly unveiled ice skating ribbon at Maggie Daley Park, Millennium’s slightly eastward kid sister.

Maggie Daley Park Ice Ribbon

(Alas, this year we are missing a vital winter wonderland piece – snow)

If you’re not frozen to the core from time on the ice, a brisk walk along Michigan Ave isn’t a bad way to make your way back north, crossing over the picturesque Chicago River with all its moveable bridges and passing by the wide assortment of glamorous shops on Michigan Ave. (Burberry and Tiffany’s, to name a few).

Of course, not all visitors are as hardy as us natives, in which case there’s plenty of taxis and buses to whisk you up to the Water Tower area.

On second thought, considering Michigan Avenue’s regularly congested nature, “whisk” might be a strong word.

Chicago Water TowerIn general, the area surrounding the Chicago Water Tower, including the John Hancock Building, is a major shopping & entertainment district, not to mention a tourist attraction. If all the time outdoors has got you shivering, the entirely indoor Water Tower Place mall offers seven floors of cozy shopping and a Mezzanine level stuffed with casual cafe & dining choices.

And speaking of food, when it comes for dinner, the area is overwhelmingly packed with restaurant options. However, because most of these are on the upscale side (not surprising, considering it’s the Magnificent Mile…), it can leave the casual visitor scratching their head in confusion.

Sitting quietly in the basement of the John Hancock building is one of the many Cheesecake Factory restaurants. Yes, yes, I know….but it’s a chain restaurant! Still, I have always felt that this particular location is one of the most fascinating when it comes to the interior design. You begin to feel as though you’ve stepped into some kind of otherworldly cheesecake version of a Willy Wonka factory.

Cheesecake Factory Hancock

Cheesecake Factory Inside

One certain thing to be said about The Cheesecake Factory is that it’s just downright solid. Tasty food, vast selections, even vaster portions, and, well, need I mention dessert?

Most times there’s also some kind of holiday display in the basement lobby just outside The Cheesecake Factory’s main entrance. One year I was treated to the most incredible toy train/winter wonderland set up I had ever seen. Throughout my childhood my grandfather’s entire basement always hosted a massive private model railroad, and that couldn’t begin to rival what was on display that evening.

Another great perk of dining in the basement of the Hancock is the ease with which you can transition up to The Signature Room after dinner, the perfect spot for a digestif with a view.

The Signature Room is a restaurant and lounge on the 95th floor of the Hancock building. To be frank, I do not recommend the restaurant itself, which is overpriced and underwhelming. However, to fully enjoy the incredible views The Signature Room offers without putting your pocketbook through the ringer, drinks (and perhaps dessert, if you skipped it after dinner) are just the ticket.

Beholding the grand city through the panoramic glass windows, laid out at your feet and alight with bustling life for miles in all directions, it almost seems for a moment as if the entire city of Chicago is decorated in celebration of a festive holiday season.

Have you visited the Magnificent Mile during the holidays? What were your favorite stops? Please share!

Filed under: Travel

Leave a comment