How I spent one day in Chicago

Chicago is a beautiful city. Set on Lake Michigan with the Chicago River running through it, it has a gorgeous skyline that offers an eclectic mix of architecture — old, new, glass, concrete, round and square  — Chicago’s skyline has a little bit of everything.

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I was lucky enough to have spent a week in Chicago a few years ago over Christmas, and honestly, when the prospect of going back to the city for a day came up, as much as I loved Chicago, I kind of felt like I had already ‘been there, done that.’

But, and this is a big but, I am so glad I decided to go back anyway.

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A city can change a lot depending on the season, and therefore so does the way you experience it. Last time I went it was a bitter Chicago winter, I was wrapped up in my thickest winter coat, the streets were lined with fairy lights and the shop windows decked out for the holiday season. This time it was a gorgeous summer day.

I only had half a day or so to spend in the city as I was merely using it as a rest-point during my drive out West (you can read about my move to Arizona here.)

So what’s the best way to see Chicago in two hours or less? 

By river of course.

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It was a family member who actually suggested a river tour as a ‘must-do’ thing when one goes to Chicago. Seeing as the last time I was in the city the river was a good as frozen over, this was definitely something new. I’m also a huge architecture buff. I could take photos of and look at buildings all day long, and many of the tours are advertised as architectural river tours — right up my ally.

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I booked my tour with Wendell Boats who advertise as being “Chicago’s Original Architecture Tour.”

The tour cost $35.50 and you also get a good deal on parking if you use your ticket/tour discount code. I got six hours of parking for $16, in pretty much central downtown Chicago, not a bad deal at all.

The tour lasts about 75 minutes and you see the three major avenues of the river.


The tours run every 75 minutes throughout the day and there are also a variety of other kinds of tours you can take if you like. Wendell Boats  (there are other companies as well) offers a Signature Lake & River Tour, a Chicago Sunset Cruise, a Chicago River Experience, a Chicago Fireworks Cruise and a Chicago River Bridges Tour. Whatever tour you decide to take, if you only have a limited amount of time, or if you want to see a lot of the city from a different and beautiful perspective, then a river tour is the way to go!

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Just a heads up — the architecture tour leaves from the dock by Trump Tower. This is also where you can apply one of the parking deals. Do with that information what you will.

Because I had an extra hour or two to spare in my parking, I decided to walk down to Navy Pier after my tour finished. While it was nice to see a bit more of the city, and the vantage point from the end of the pier offered a beautiful look back at the skyline, I was a little underwhelmed.

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To be fair, I was there on a Tuesday afternoon and couldn’t really sit down and enjoy the pier (Beer Garden) as I would have liked to because I had to jump in the car and drive to Iowa that evening.

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I think the Pier would be a great place for families, or groups who have more time and can spend a whole afternoon hanging out. For a solo traveller on a tight time budget it wasn’t anything special. However, it was one of the few things I hadn’t done in Chicago and therefore am glad I did.

Overall the tour was a real knock out and 10/10 would recommend. It was a great way to see a lot of the city in a condensed amount of time.

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13 Comments on “How I spent one day in Chicago”

    1. Ah so cool. Glad I could help, when you do end up going feel free to reach out again. I have many other suggestions that I have yet to compile into a blog post from when I went a few years ago. Love this place x

  1. The sky is so blue in your photos!
    Going by river sounds like a perfect idea and if i ever go in the future i’ll be looking for this blog post again. Thank you for sharing 🙂

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