Family Adventures in Chicago: A Boat Tour Through the City’s Iconic Architecture

I’ve been mostly off the grid (sort of) for the past five days because I took a family vacation to visit a friend in Chicago. I wasn’t completely tech-free, I used my phone to snap tons of photos of the city and my kids, and I definitely relied on it for directions (because I’d have been lost without it!). But I stayed away from web browsing, videos, and even Hive, though I did sneak on for a few minutes one night. I wanted to give my full attention to my family this weekend, especially with my oldest starting kindergarten this Wednesday (a bittersweet moment for this proud parent).

My oldest loves building things with Legos, wood, or anything else he can find—like toilet paper rolls, paper, and pipe cleaners. So, of course, we had to check out the architecture of Chicago, and what better way to do it than with a boat tour? We decided to go on the Shoreline Sightseeing architecture cruise.

We had to take cover on the lower deck with most of the other passengers for about 15 minutes when it started pouring rain. In our absent-mindedness, we left our umbrellas at our friend's place, so we did miss a few buildings. But overall, the tour was great, and my kid loved it.

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The skyline was amazing, showcasing a variety of architectural styles. One of the first buildings we saw, and one of the tallest in Chicago, is the Trump International Hotel & Tower® Chicago. While I'm not a fan of Trump, this building is worth mentioning because its architect, Adrian Smith, also designed the Burj Khalifa. He is also involved in the design of the Jeddah Tower which will surpass the Burj Khalifa!

One of my kid’s favorite buildings was the Marina Towers, mainly because its design stood out from all the others we saw. The building, along with a few similar ones, was designed by Bertrand Goldberg, who believed his buildings should foster a sense of community.

Another iconic building we visited was the Sears Tower, though it’s now called the Willis Tower. It’s had that name for about 3 or 4 years. We went up to the Skydeck and stood on the glass floor, looking straight down, but I’ll save those photos for another time. You only get 90 seconds to take pictures before you have to wait in line if you want another turn on the glass floor.

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At this point, I had basically stopped listening to the tour guide because I couldn’t absorb any more information. It was great, but it was just too much. I decided to just enjoy the rest of the tour until the very end.

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I finally tuned back in towards the end of the tour as we passed near where we were staying. The St. Regis is an incredibly expensive hotel and condominium complex, with floors 71 and 72 selling for over $20 million combined! The architect of the building, Jeanne Gang, is known for designing the tallest building ever created by a female architect.

I'm not sure I’d ever spend millions on a condo, even if I owned an entire floor. It just doesn’t seem worth the money. Plus, I’m terrified of heights, so being near the windows would make me really uncomfortable.

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The St. Regis is the one just barely covered by clouds. It has a pretty cool wavy design to it. After passing this location we made a U-Turn which allowed us to get to get some great skyline photos before the tour ended.

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Overall, if you’re ever in Chicago, I definitely recommend this tour, it’s worth every penny. Just be sure to check the weather before you go. Rain on the boat isn’t enjoyable, and it can be uncomfortable if it’s really hot since there’s no shade and the cruise doesn’t move very fast

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