The Shoreline Sightseeing Architecture Boat Tour Is Totally Not Boring

As part of the North Iowa Bloggers, I was provided a free Architectural Tour by Shoreline Sightseeing. All thoughts and opinions are 100% honest and my own.


Near the beginning of the Shoreline Sightseeing architecture boat tour, our guide stated, “If you’ve never seen Blues Brothers, than shame on you. It’s a great American classic,” with a straight face. I knew we were in excellent hands.

Now, I must confess, guided group tours and boat rides aren’t usually my thing. When I learned Shoreline Sightseeing invited us to go on a 75-minute long architecture cruise with a group on a boat, I felt apprehensive. An architecture tour could be really boring, but this was totally not. Shoreline’s boats cruise up and down the Chicago river, through the heart of its downtown. The river provides the perfect passageway from which to view the city’s most notable buildings.


To board the Evening Star, we walked from our hotel to the Navy Pier area.


We chose seats along the side rails and some grabbed cocktails and beer from the downstairs floor. I was surprised to learn they were affordable (and strong) at about $5 each.


As the boat began to move down the river, our tour guide Victor introduced himself and shared that he’s currently an architecture student. His passion for Chicago architecture shone through and felt contagious. He not only identified notable buildings and shared interesting facts about them, but did so in a humorous and engaging way. Buildings are steeped in so much history and provide a fascinating backdrop to learn about a community’s dynamics.


A few of the buildings and spaces we passed were unoccupied. Victor shared his hopes for how these spaces could be used to both maintain the city’s beauty, and meet its residents needs.


I left the boat tour feeling very pumped about architecture.


 Overall, I found learning about Chicago architecture on a boat and watching the sun set to be a very a pleasant and (interesting) way to spend an evening. As the tour ended, Victor  left us with some words of encouragement.

“Don’t forget to look up. Even if the building is only two stories, there’s something interesting about it.”

Before You Book: Tickets cost between $35-39 for adults, $18-20 for children, and infants are free. According to the website, booking online gives you a $5 discount per ticket. If it’s a sunny day, don’t forget to bring sunglasses or a hat. The top of the boat has no canopy or shade to interfere with viewing buildings. However, you can move to the bottom level of the boat for shade, restrooms, or beverages.


  1. Monica Jertson Cateron

    I absolutely LOVE Chicago !!! So much to do and see !

  2. Road Tips

    My wife and I went into Chicago as tourists during August about 4 years ago. I go in so often for business that we decided to “go and do and see” for three or four days. (I wrote about it here – One of the things she wanted to do was the architectural boat tour. I wasn’t too whippy about doing it – it was 90 minutes on a boat. But I have to tell you, after the boat tour was over, I was ready to go again! I learned so much about buildings that I had passed dozens of times over the years and never knew their story. But then they took us out on the lakefront to see the skyline – that was pretty cool.
    For my recent birthday, my wife treated me to a guided cultural/culinary/architectural walking tour of Chicago’s Pilsen – or “Little Mexico” – neighborhood. That was simply out of sight. I’ll have the whole story up on Road Tips this Saturday.

    • Jeni

      I will read about your experience for sure. It’s fun to hear from another skeptic who also had a great time. The quality of the tour was so great-because of the guide. The walking tour sounds amazing. I will look for that post.

  3. Donna Hup

    Victor was the best and I was totally surprised how interesting this tour was. I had lots of fun 🙂

  4. Beth Ann Chiles

    This was probably my favorite part of the trip (other than the food). I loved how knowledgeable Victor was and how he interjected his ideas and humor into the talk along the way. And hey–you didn’t have to take any motion sickness pills for it. Win!

    • Jeni

      I probably had some in my system from the plane;) Still have 95 left. . .

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