This morning, we set off on foot to Union Station—a quick 10-minute walk from the apartment—to begin our insider’s guide to Chicago’s architecture walking tour with our guide, Avery. The kids were less than thrilled at the idea of a walking tour (tough crowd), but participation was non-negotiable. And to be fair, TJ ended up really enjoying the tour.
At Union Station, Sophia’s attention was quickly diverted by a group of Amish travelers, which ended up being the most exciting part of the morning for her. Meanwhile, Mark & I were captivated by the Great Hall’s soaring ceilings and grand Beaux Arts architecture. Designed by Daniel Burnham—one of Chicago’s most influential architects—we learned that the station’s massive glass skylight was covered in tar during WWII to block out light and remained that way until 1991. Unfortunately, the damage was beyond repair, and it had to be completely replaced—a process that wasn’t completed until 2019 due to the staggering $22 million cost.
From Union Station, we made our way to some of Chicago’s most iconic buildings, starting with The Rookery. Completed in 1888, it’s one of the oldest standing high-rises in the city and a perfect example of how Chicago blends historic charm with innovation. The building’s exterior was designed by Burnham and Root in a Romanesque style, and the lobby was completely redesigned by Frank Lloyd Wright in 1905. Light filters through an intricate glass ceiling onto a grand white marble staircase. Even the kids had to admit it was pretty cool (though they’d never say that out loud).
Next up was the Field Building, now known as the LaSalle Bank Building. Built in 1934, this Art Deco skyscraper was once the tallest building in Chicago. What makes it stand out is how it blends functionality with elegance—streamlined stone and stainless steel detailing, plus a massive banking hall that looks like it’s straight out of a 1930s movie set. You half expect someone in a pinstripe suit and fedora to walk by.
We then stopped at the Marquette Building, another Burnham and Root design from the 1890s. While modest in height compared to modern towers, this building is rich in history. The lobby mosaics are stunning—created by Tiffany Studios, they tell the story of Father Marquette, the French missionary and explorer the building is named after. The craftsmanship is insane, and it really brings the space to life.
Our tour continued to the Palmer House at the Hilton. Originally opened in 1871 as a wedding present from Potter Palmer to his young wife Bertha Honore (and then rebuilt after the Great Chicago Fire), this is less a hotel and more a slice of living history. The gilded lobby is like stepping into a European palace—chandeliers, frescoed ceilings, and a heavy dose of old-world glamour. Fun fact: until it was closed down for 3 months during Covid, it was the longest continuously operating hotel in the U.S.
We continued to Marshall Field’s, now Macy’s, but still very much a Chicago institution. The grand department store is more than just a shopping destination—it’s part of the city’s architectural fabric. The Tiffany-designed mosaic ceiling alone is worth the visit, and it gave us a sneak preview of what was to come…
Our final stop was the Chicago Cultural Center, home to the largest Tiffany glass dome ceiling in the world. It’s 38 feet in diameter and made from over 30,000 individual pieces of glass. Pictures don’t do it justice.
We did tip our guide Avery, though he lost a few dollars to the family’s “holiday swear jar”. Sorry, Avery—rules are rules.
Next on the agenda was a scenic albeit rather chilly stroll along the Chicago Riverwalk, soaking in the city’s stunning architecture—Trump Tower, Tribune Tower, Marina City, and the iconic Wrigley Building all putting on a show. We eventually emerged onto North Michigan Avenue, where the unmistakable scent of Ghirardelli chocolate practically pulled us in.
We made a quick pit stop for some cozy hot cocoa, though the kids had their eyes firmly set on milkshakes. Recharged and slightly more sugared up, we popped into Target for a few essentials, then continued on our way toward Navy Pier.
Navy Pier stretches about 1,000 meters into Lake Michigan and covers over 50 hectares, it’s packed with shops, restaurants, theaters, family attractions, gardens, and more. Our first stop was Garrett Popcorn—an institution in Chicago since 1949. We grabbed a few flavors and sat down to enjoy a little snack break.
Then it was time for the Ferris wheel. The current 60-meter wheel, installed in 2015, was worth the ride. We got three full rotations with sweeping views of the city and lake. It was cold waiting, but thankfully the line moved quickly.
Back in town, we split up for some shopping. After Mark & AM found new pairs of sunglasses, the boys veered off toward the so-called “Sports Museum”—a.k.a. the pub—while we girls hit the shops. Brandy Melville and Aritzia were found, and the credit card took a bit of a hit, but the girls were happy.
Hunger eventually brought us all back together at Water Tower Place. A small miscommunication about bar access led to the girls being temporarily denied entry, so we all reconvened at The Cheesecake Factory downstairs after the boys did actually see the Sports Museum. It was the usual: loud, crowded, and a wait—but the food was reliable and hit the spot.
We wrapped up the day by catching the El (Chicago’s metro system) home. It was fast and convenient, though the kids were convinced we’d be mugged or worse. I didn’t have the heart to tell them I overheard a security guard talking to someone about them carrying a knife.
