Travelers Roundtable

Hear Robert Bundy discuss Christmas in Chicago and other weekend getaways within easy reach of Milwaukee on The Travelers Roundtable on 89.7 WUWM Public Radio Milwaukee’s Lake Effect with Mitch Teich.

Chicago has been called “the most American of American cities,” so it should come as no surprise that a Chicago Christmas offers visitors some of the most archetypically American holiday experiences to be found anywhere. From browsing the charming store windows at Macy’s to shopping your way down The Magnificent Mile to sipping cocoa or mulled wine at the Christkindlmarket on Daley Plaza to taking a regal afternoon tea under a grand, 20-foot-tall Christmas tree in a posh Michigan Avenue hotel, Chicago conjures a postcard-perfect dream of Christmas that few big cities can equal. If you want to get in the Christmas spirit, get all your gift shopping done in one fell swoop, and treat your family to a wonderful holiday in the process, consider arranging an overnight getaway to the Windy City.

Safe Harbor at The Peninsula 

My wife and I lived in Chicago for many years and even though we lived in the nearby Lincoln Park neighborhood, we often found that getting to and from downtown could be exhausting. If you really want to be able to enjoy the wealth of experiences that the city’s heart has to offer, you need to have a comfortable refuge that is centrally located so you can relax, get rejuvenated, and then charge back into the excitement feeling refreshed. There is no finer place to do just that than The Peninsula Chicago, a 5-Star, 5-Diamond hotel recently rated the #1 Big City Hotel in America by readers of Travel & Leisure. 

A Room with a View

Architect Elkus Manfredi created the design for this splendid hotel, thoughtfully set back from Michigan Avenue so as to not disrupt the traditionally smaller scale of what has been long been regarded as the ChampsElysees of the Midwest. Inside, The Peninsula is lavish and bright, with a two-story lobby crowned by crystal chandeliers framed with gold-leaf ceilings in an Art Deco style that is a further reference to the district’s original glory days.

The hotel has three restaurants including The Lobby, which offers contemporary cuisine as well as hosting their delectable afternoon tea. We relished the Colorado rack of lamb, and their appetizer of foie gras torchon with orange, gingerbread and lemon balm. But the real revelation was their flagship restaurant, Shanghai Terrace, where we had an astonishingly good meal. Try the braised abalone, or the chilled pork ear terrine, or the black fowl with Chinese yam soup, wolf berries and herbs. Their dim sum—particularly the foie gras and duck dumpling—was worth the trip to Chicago all by itself. I could go on, and I’m definitely going back.


After a long morning of shopping, be sure to take a midday break and treat yourself to a pampering visit to the Peninsula’s award-winning spa. This is a tranquil, serene space clad in warm, dark stone and soft lighting. There are a wealth of options here, including everything from a private, in-room massage to full-day Spa Journeys that meld Asian and Ayurvedic techniques and philosophies.

The Peninsula also has a wonderful swimming pool occupying a bright, lofty corner framed with tall glass walls—it’s like swimming in a jewel box—that is deservedly popular with families. While the public spaces and sublime experiences of The Peninsula inspire, what we loved most about the hotel was our sprawling yet cozy room and the dazzling views on three sides of the bustling streets below.

The Grand Avenue

The stretch of Michigan Avenue known as The Magnificent Mile brims with energy at all times of year, but from Thanksgiving to Christmas it also glimmers with acres of holiday finery, sprays of evergreens and radiant splashes of red, gold and silver. The day-trippers have to wrestle with traffic and parking headaches, but staying overnight, we’re footloose and fancy-free, enjoying rubbing elbows with the other walkers, and it’s a relief to be out of our car and able to drink in the sidewalk atmosphere at our own pace.

Whatever it is, you can find it here; we certainly did. The Mag Mile always puts me in mind of that antique phrase, “an embarrassment of riches.” And while you will find Cartier, Tiffany and Co., Neiman Marcus and the other exalted names, you can also find shops that cater to every budget, all mere spitting distance from Water Tower Place at 600 N. Michigan Ave.

Shoppers at Chicago's Kristkindlemarkt.


When our arms are full of gifts, we pop back to The Peninsula to deposit our purchases in our room, and then charge back to the streets unencumbered. This is shopping without the dropping, and it’s a far more pleasurable experience than the endurance test it would be if we weren’t staying the night. We shop our way south, cross the Chicago River, hang a right to go west and walk a few short blocks to get a taste of Europe.

The Christkindlmarket

Chicago’s largest open-air Christmas festival is a relatively recent addition to the holiday scene here, kicking off in 1996, but it was an instant hit and remains a favorite of Chicagoans and tourists alike. Now set on Daley Plaza, the Christkindlmarket features a variety of German/European classic foods, drinks, crafts and gifts presented in row after row of rustic market stalls all huddled around the city’s largest Christmas tree. Feast on everything from crepes to sausages and from roasted nuts to cotton candy. Savor stollen, gingerbread, marzipan, English toffee, German strudel and rich chocolates. Then wash it all down with hot, spiced wine or excellent German lager or bock in the beer hall, or brave the winds out in the open at one of the many communal tables. The market stalls are great places to find adorable little handcrafted stocking stuffers, hand-knitted sweaters, hats and gloves, blown-glass ornaments and much more.

The market is also home to Santa’s House, a charmingly realized cottage that offers kids the chance to tell Santa their heart’s desire and make their case for deserving it. An Elf takes your child’s picture with Santa and, unlike every shopping mall I have ever visited, the photograph is free. You’re given a card that directs you to a website where you can download the picture at no charge, courtesy of the UL Company. It’s a nice gesture. And their Santa, well, it’s clear that he’s the real one.A magical Christmas window along State Street

The Dream Windows

The Marshall Field & Co. building on State and Washington is a National Historic Landmark, is listed on the National Register of Historic places, and has been an iconic symbol of Chicago for more than 100 years.

Now owned by Federated Department Stores, it currently houses a Macy’s, but at least from the street, the spirit is unchanged.

Walk down the broad sidewalk of State Street under a canopy of decorative trumpets and enjoy the animatronic displays of romantic Christmas scenes. Watching the children watch the clockwork figures move is just as much fun as the vignettes themselves. It’s heartening to see that even in an age of technological fetishism and videogame attention spans, a mechanical holiday shop window can still transfix a child. My wife and I watch our son as my parents watched me, gazing past the cold glass at visions of warm hearths and glittering Christmas dreams.    

Story and Photography ©Robert Bundy

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Robert Bundy has visited more than 300 cities and 32 countries in the last ten years and still gets a charge out of getting his passport stamped. He convenes The Travelers' Roundtable is part of Lake Effect with host Mitch Teich for WUWM 89.7 Public Radio Milwaukee.