Growing up in New York City, I always loved riding the D train into Midtown at Christmas to see the the decorations at Rockefeller Center, the window displays on 5th Avenue and the general holiday cheer.
So, I have always worked to give my kids a similar experience by taking them to Chicago every holiday season.
Ten years ago, I brought my preschool-aged daughter for our first (but definitely not last) daddy/daughter trip and we had an amazing time checking out checking out decorations, the Christmas market, ice skating and more.
To mark the anniversary, me and my girl – not so little anymore – hit the road.
Arriving at the Sheraton Grand Chicago Riverwalk, we were wowed when we stepped into our Elf Life Suite.
The space itself was pretty incredible with a separate bedroom, two bathrooms, a butler’s pantry and a sprawling living room with a view of Lake Michigan and the Chicago River, directly across from one of my favorite Windy City buildings – the Jeanne Gang-designed St. Regis (aka Vista Tower).
But that was just the start. The entire suite was adorned with holiday decor, stockings, lights, elves, snowflakes and a full-size, fully decorated Christmas tree.
There’s also a hot chocolate bar, candy canes and an elf you can take home.
The package – available through Jan. 7 – also includes breakfast and late checkout, and it’s available through ....
The hotel is centrally located, just steps from the Michigan Avenue, Navy Pier and other attractions and did I mention that the view is incredible?
After settling in, we hit the streets, checking out the Apple Store in its striking Norman Foster-designed riverfront home, enjoying pandoro samples at Eataly and doing a little holiday shopping at Water Tower Place.
Along the way, seeing the door open, we popped into the stunning St. James Cathedral, whose bell tower was one of just two structures to survive the 1871 Great Chicago Fire (the water tower was the other).
Then, we headed over to State Street, which always wows at Christmas and wandered Macy’s in the old Marshall Field’s building with its gorgeous Tiffany mosaic dome. We also checked out the tree in the Walnut Room.
On our many visits to Chicago, we never pass the Chicago Cultural Center without stopping in. It’s one of the most beautiful buildings anywhere and it’s just a joy to be inside.
That the latest Architectural Biennial is currently on view meant we got to do a little exhibit exploration, as well as just breathing in the incredible Tiffany dome, mosaics and other details of the 1897 Shepley, Rutan and Coolidge-designed former public library building.
Wandering over to the Palmer House – where we stayed on that first visit a decade ago – we took in the holiday cheer and then went to the outdoor German Christkindl Market to hear the carolers and peruse the many types of ornaments on offer.
Ten years ago ago, I navigated the market with my companion perched atop my shoulders. This time, she walked at my side.
For dinner we experience Mercat a la Planxa at The Blackstone, one of our favorite Chicago hotels – which has a great history you can read about here – where the John F. Kennedy Suite is super decked out for the holidays with Christmas- and presidential-themed decor.
There are also board games, an ornament-making station, a record player and some festive vinyl and more.
Come Jan. 1, the suite’s theme will shift to honor the late Joe Segal and his legendary Jazz Showcase which, for a time, occupied a space off the hotel’s lobby.
Mercat is a Spanish-themed restaurant with tapas and more. We had bacon-wrapped dates doused in a bleu cheese fondue, ribeye, spicy shrimp, incredible lamp chops, sauteed broccolini, a delectable cheese and salumi board and, for dessert, churros with a chocolate sauce and a chocolate cake.
We sat and chatted, played guessing games, talked about our many travels since that first daddy/daughter trip and just enjoyed each other’s company.
Walking back to the Sheraton, we strolled through Millennium Park, passing the decorated trees, a lovely Christmas tree and the Frank Gehry-designed Pritzker Pavilion – beautifully lit.
Back in the room, we made the most of the hot cocoa bar and the comfy living room before hitting the hay in anticipation of day two of our little getaway.
On day two, after grabbing a quick breakfast sandwich and donut at our favorite, Do-Rite, we checked out a couple museums, including the interesting (and free) Money Museum at the Federal Reserve Bank and the Museum of Contemporary Art, which the kids have been visiting all their lives and which currently has a big Faith Ringgold retrospective.
Checking out of the Sheraton, we moved over to Sable, the Hilton Curio Collection hotel that opened on Navy Pier in 2021.
The bright and modern rooms at this hotel – which feel like staterooms on a cruise ship – all face Lake Michigan and perfectly placed window seats offer amazing views of the skyline and the lake.
Navy Pier was alive for the holidays, with decorations, live music and djs, an artisan market and more as part of its Light Up the Lake celebration that will culminate with New Year's Eve fireworks.
As part of the festivities, Sable is offering a Stay & Skate package that includes free skate rental at the on-site lakeside rink, breakfast and a late checkout.
One of the last times I skated was at Millennium Park on that first daddy-daughter trip, when we both took a skating lesson. While my little one took to it and now is pretty accomplished on the ice, I'm still a wall-crawler. But, still, it was fun to be out there on the ice watching how far she's progressed at it.
Just before that we were able to cross off a bucket list item we've talked about for a while – we rode the Centennial Wheel and fortuitously at sunset, so we got some nice photos and great memories.
For dinner, we headed up to the roof where we dined in the "snow globe" atmosphere of Offshore, with its glass roof, stellar views, dangling snowflakes and bright lights.
The space is big and open, with lots of outdoor seating, and the food is a mix of elevated bar fare like plump wings and fish & chips, alongside sushi, fish tacos, burgers and steak frites, which is especially good.
Don't miss the brownie for dessert. It's delectable and big enough (with two scoops of vanilla ice cream) that at least two can and should share.
On day three, we got up, headed over to the Art Institute of Chicago, which we've visited countless times over the years, including on that first trip together when, at an informal art class, we collaborated on a "cow horse" mask.
Along the way, we strolled through Maggie Daley and Millennium Parks and the awesome Lurie Garden, which manages to look beautiful even at the start of winter.
Although we've been to ArtIC on multiple occasions this year along (Dali, Van Gogh, etc.), we came back to check out the new Antonio Canova clay works – which has some really interesting videos explaining the sculptors' process – and Picasso works on paper shows.
The real surprise treat was a show of works by French sculptor Camille Claudel, which we didn't even realize was going on. Stumbling up this pretty in-depth exhibition was a real highlight.
When it was time to head home – after a quick stop for Nutella and banana crepes – we made a pact. In 2033, god willing and the creek don't rise, wherever we find ourselves, we'll reconvene for the 20th anniversary of that first daddy-daughter trip to make even more memories to carry into the future.
Born in Brooklyn, N.Y., where he lived until he was 17, Bobby received his BA-Mass Communications from UWM in 1989 and has lived in Walker's Point, Bay View, Enderis Park, South Milwaukee and on the East Side.
He has published three non-fiction books in Italy – including one about an event in Milwaukee history, which was published in the U.S. in autumn 2010. Four more books, all about Milwaukee, have been published by The History Press.
With his most recent band, The Yell Leaders, Bobby released four LPs and had a songs featured in episodes of TV's "Party of Five" and "Dawson's Creek," and films in Japan, South America and the U.S. The Yell Leaders were named the best unsigned band in their region by VH-1 as part of its Rock Across America 1998 Tour. Most recently, the band contributed tracks to a UK vinyl/CD tribute to the Redskins and collaborated on a track with Italian novelist Enrico Remmert.
He's produced three installments of the "OMCD" series of local music compilations for OnMilwaukee.com and in 2007 produced a CD of Italian music and poetry.
In 2005, he was awarded the City of Asti's (Italy) Journalism Prize for his work focusing on that area. He has also won awards from the Milwaukee Press Club.
He has be heard on 88Nine Radio Milwaukee talking about his "Urban Spelunking" series of stories, in that station's most popular podcast.
