The One In Chicago With The Experience We Trained For Years Ago

Unless you’ve known our family personally for a long time, here’s a fact that might surprise you: We lived in Chicago for 10 months.

It was the coldest, snowiest, and longest winter ever! But, it was also a really special time for our family. Long before moving there, Chicago ranked as one of our favorite cities in the world. In hindsight, living there felt like an extended vacation.

One of the best parts of living in such a cool city was that a lot of people came to visit. Especially during the warmer months, we had a revolving door of guests.

Naturally, we came up with a pretty good lineup of sights to see around the city.

Hands down, our favorite touristy activity was the architecture boat tour around downtown.

Real quick (and then I promise I’ll circle back to our own boating adventure) for anyone not familiar with the geography of Chicago…

The city sits on the shores of Lake Michigan. And then the Chicago River runs right through the heart of downtown with skyscrapers built along both the Lake and River fronts. It’s a dream for boaters!

Anyway, when we lived in Chicago we went on the Architecture Boat Tour at least 7 or 8 times with a variety of visiting friends. In fact, we’d done it so many times we had the whole script memorized. It would have been easy for us to give the tour ourselves, if we’d had a boat…

Fast forward 7 years. We couldn’t wait to get our boat to Chicago!

It’s a major highlight and destination city on America’s Great Loop.

In fact, it’s wildly discussed during the boat buying process for 2 reasons:

  1. To boat on the River through the heart of downtown, your boat must be able to clear a bridge that’s fixed at 17 feet. Otherwise, you have to take an alternate route that bypasses the city itself. FYI: Our boat is 16′ 9″.
  2. Just south of Chicago is the lowest fixed bridge on the whole Loop. It’s 19 feet. The only way to circumnavigate the Eastern part of the US by water goes under this bridge.

After boating through the Great Lakes, Chicago feels like the prize at the end of a difficult journey. We could actually see the outline of the downtown skyscrapers on the horizon days before we arrived.

Our family decided to spend a few days in one of the downtown marinas. Quite honestly, it was nothing like we hoped it would be when we started the Loop.

We didn’t get to see family or friends. Nor did we visit any of our favorite places like the Shedd Aquarium or the Museum of Science and Industry.

But, we did experience the city in a way that we never got to when we lived there- like true downtown residents!

Our family went for a run and bike ride along the lakeshore path. We hauled groceries on foot several blocks from the grocery store. And we ate all of our favorite food delivered right to us at the marina.

Finding new experiences and making new memories in a city where you’ve already got a million is tough, but we managed to do it!

But the best was yet to come…

After locking into the Chicago River we took our boat straight through the heart of downtown.

We literally did our own version of the architecture tour. It felt like we’d trained for it years earlier. Brent and I could easily identify most of the buildings and even throw in some fun facts we recalled from the real tour.

The experience was so cool and so surreal. We ended up doubling back a couple times and riding through the city.

There really are just no words to describe how incredible this experience is, so instead I’ll share a collage of pictures…

Our kids finally got tired of the architecture tour commentary, so we moved on to talking about all the great memories we’ve made in Chicago. It was truly a great day.

Eventually we moved on and got to experience a whole different side to the city- the industrial waterway.

We navigated the river and took an unusual turn back towards Lake Michigan on the Little Calumet River (this is part of the alternate route I mentioned earlier for boats that can’t fit under the Chicago bridges.)

At this point in our journey we took a little break. I’ll go into more details on that in my next post.

As always, thanks for following along on our crazy adventure! You may also enjoy reading:

The One With The Great Lakes

Chicago In A Weekend

The One Where The Journey Begins

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