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Over the years, Chicago has become one of my favorite cities in the U.S. With great public transportation, amazing pizza, fantastic entertainment options like improv and blues, and a picturesque location on Lake Michigan, Chicago wins a lot of points in my book.

Another thing the Windy City has going for it? Interesting architecture.


Chicago’s skyline truly does represent the marriage of old and new. Buildings like the 1920s Tribune Tower sit next to the 1960s-era “corncobs” of Marina City and the sleek and shiny Trump Tower of the new millennium. A stroll along any street in downtown Chicago will reveal a melding of architecture styles, from neo-gothic to modern and everything in between.


And while you can see Chicago’s architecture from many vantage points — on foot, by bike, or even from above inside the Willis and Hancock towersthe best way to admire it is definitely from the water.


If you’re headed to Chicago this spring or summer, be sure to book a ticket on one of the city’s popular architecture cruises on the Chicago River. And do it with the Chicago Architecture Foundation.

The CAF was founded in 1966, and has since become the leader in architecture and design knowledge in Chicago. The Foundation offers tours on foot, on bike, and even on segway. But my favorite option is definitely their boat tour.


The 90-minute CAF river cruise gives visitors a comprehensive look at how Chicago has transformed over the past 100 years. The tours are led by volunteer tour guides known as docents — suggesting a museum-quality knowledge of more than 50 buildings along the Chicago river, as well as a passion for both architecture and the city. I’m always a big fan of tours with volunteer guides, because I know they are guiding simply because they love to do it.

If you can hit a sunny, warm day in Chicago, here’s what you can expect to see along your cruise:



The Willis Tower (which is actually 9 different towers stuck together).


Residential buildings along the River.




Marina City


Tons of cool bridges.


Merchandise Mart, once the largest building in the world with 4 million square feet of floor space.


Lots of cool reflections.




Trump Tower.


The view from Lake Michigan.

Needless to say, this is one of my very favorite things to do in Chicago. Whether it’s your first or fifth time in the Windy City, go on one of these cruises if you haven’t already — I guarantee you’ll learn something!

*   *   *

If You Go…

Price: $37.85 per person

Length: 90 minutes

When: Cruises run from mid-April to mid-November (check the schedule for exact times)

Where: Groups should meet at the southeast corner of the Michigan Avenue Bridge


Is this an activity YOU would want to do in Chicago?



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14 Responses to Chicago From the Water

  1. memographer says:

    I love the river cruises. I always try to get on a board if there is a river in city I travel.
    You got a good collection of Chicago Cityscap pics. Great job!!

    • DangerousBiz says:

      I like boats in general, and this is definitely a unique way to see Chicago! It’s not in every city that you can see skyscrapers from this angle!

  2. memographer says:

    “Cityscape” typo… sorry

  3. Nancy says:

    Thank you for the gorgeous photos of Chicago from one of the CAF boats. All our tour guides are highly trained volunteers. I give several of the walking tours that CAF offers. We have 90 tours in all. Check architecture.org for more info.

    • DangerousBiz says:

      I was really impressed with our guide; like I said in the post, I love volunteer guides. They are always so knowledgable, and so passionate!

  4. Sofie says:

    Yup, it’s definitely something I’d do on a sunny day.
    Although I’ve been to London several times before, last time was the first time I took the river bus on the Thames and I absolutely loved it. It offers a totally different view on a city.
    Sofie recently posted..My first award

    • DangerousBiz says:

      Seeing a city from a river is always neat. I need to do more of the river buses in London; the only time I took one, it was pouring down rain so I didn’t really get to fully appreciate it!

  5. The architecture river tour is my favorite tourist activity in Chicago. Everyone who visits should book it. Right after visiting the Bean and getting some deep dish!
    Scott – Quirky Travel Guy recently posted..Cool Chicago: The Green Mill, Al Capone’s favorite jazz club

    • DangerousBiz says:

      I agree! Definitely one of my favorite touristy things to do in Chicago! (Though my #1 is probably going to see some improv!)

  6. Ed says:

    You have to level with me. The pictures are NOT from this year. The trees still have no leaves. It is too damn cold here!
    Love the blog, though! Can not WAIT to leave the states, retire, and just travel around. Good Luck!


    • DangerousBiz says:

      Nope, I did not take this cruise (or the photos) this year. Actually took it in October 2011, I believe. But that’s what great about a travel blog – content like this can be posted whenever! I chose now since the cruising season is just beginning for the year in Chicago!

  7. [...] geographically, at least — but Chicago is no flyover city. To get a true sense of Chi-Town, you’ve got to head for the water. [...]

  8. [...] Chicago from the Water by Dangerous Business: Nice shots of Chicago which were taken when Amanda did a river cruise [...]

  9. […] Chicago from the Water by Dangerous Business: Nice shots of Chicago which were taken when Amanda did a river cruise […]

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