22. Nighttime kayak on the Chicago River

If you haven’t had the chance to see Chicago from a kayak on the Chicago River, I suggest you drop what you’re doing and head out there right now. It is an amazing experience being so close to the water with the city traffic and boats moving so quickly around you. It can really make a person appreciate the builders and designers of this amazing city.

This kayaking tour was a combo mother’s day/birthday present for my mom. And, unfortunately, Chicago weather has been so terrible this summer that we had to wait until August to cash it in (2-3 months after both events). There were a few days my mom and I talked about going, but then the weather forecast called for rain so we decided against it (of course, by the time the day came it would arrive with glorious weather, but isn’t that typical Chicago?). Finally we picked a day and decided that, rain or shine, we were going. We could always reschedule if necessary.

So the day arrived. And in true kayak-planning fashion, the weather called for rain all day. The morning was cloudy, but the rain never made an appearance. At noon I checked the forecast again – rain from 4-7 (our kayaking trip was scheduled from 6-8). Called my mom and we decided to keep the reservation. At 4pm I looked out of my office window to the most glorious summer afternoon ever. 75 degrees and sunny with a cool breeze. We couldn’t have asked for better weather. At that point, the forecast had put the rain later in the evening, so we were golden.

My mom met me at work and we headed over to Kinzie Chop House for the happy hour specials. It’s pretty much the best deal in Chicago – half price appetizers with the purchase of a drink from 4-6pm. And the appetizers are on the bar menu, so the prices are already low (there’s both a $5 and $10 menu).

I had a Living Social deal for this kayaking tour, but even the typical sunset tours are only around $70 so it’s still somewhat affordable. Luckily my mom is awesome (and conscious of my budgeting goals), so she doesn’t judge me for choosing 1/2 price appetizers for dinner and Living Social deals. We arrived to their location just as one of my favorite Chicago moments was happening:


We got into our life jackets and headed over to the kayaks. There were about 20 people total in our tour, and everyone had the choice between single or tandem kayaks. Deciding that we both wanted to paddle, my mom and I went with the single kayaks. These kayaks are state-of-the art and you will not tip over in them unless you lean all the way over the side. Trust me, I’ve been in some wobbly kayaks and I leaned farther over the sides of this one than I could in most other kayaks.

One happy mama.

One happy mama.

We started just east of the Michigan Avenue bridge:



And made our way to Wolf Point, which is where the North, South, and Main branches of the Chicago River meet:


Once we were out on the water, our tour guide would give us a location to kayak to. Once there, he would tell us about the architecture around us. Being an Art History/Interior Design major, I totally geeked over this part of the tour.

I have been on a lot of architectural tours around this fair city. One story I had never heard is the story about the building at 35 E Wacker. I didn’t get a picture of this one, but it was originally called the Jewelers Building. It would be risky for the diamond merchants to walk from their vehicles to their offices, so the building had an auto elevator which would allow merchants to drive their vehicles right into the building (and avoid muggings). Seriously, people would load up their vehicles with the goods and drive right into the building and the elevator would take them directly to their floor. How’s that for service?! Even more fascinating is that Al Capone used the top floor restaurant (previously known as the Stratosphere Lounge) as a speakeasy during prohibition (of course he did!). One reason I love Chicago architectural tours: I learn something new every time I go.

I digress. Back to the sights:

Great building, except for the tacky logo on the side.

Great building, except for the tacky logo on the side.

And because this was a sunset tour, we saw the sights both with lingering daylight and gorgeous nighttime views:

I know it's lame of me to think the building I work in is so awesome, but at this view, how can I not?!

I know it’s lame to think the building I work in is so awesome, but at this view, how can I not?!

And even with all of the kayaking, we still had time for a selfie (duh).


All around a great experience. I think my mom enjoyed herself too.

We could NOT get her off the water!

We could NOT get her off the water!

Special thanks to Urban Kayaks for the amazing experience and to my mom for being adventurous enough to join me!

Post Script: it never rained that night. Not even a drizzle. Typical Chicago weather.