It took me a long time after moving from Philadelphia to “know” my surroundings in Chicago and feel at home. To a degree, my sluggish progress in understanding what I saw impelled me towards the formal study of urban spaces — their history, their people, and the layered infrastructures they provide.

I realized last August that it’s possible to circumnavigate Chicago by kayak — see map. Lake Michigan forms the eastern rim of course. The southern edge of the loop runs along the Little Calumet River and the Calumet/Saganashkee (Cal/Sag) Channel. Heading north all the way to Wilmette, one can take the Des Plaines River, the Chicago Sanitary and Ship Canal, the Chicago River, and ultimately the North Shore Channel. I got it in my head that it would be a cool way to see the city, and in particular its natural and more-industrial sectors. I finished about 2/3 of the tour (65 mi) before it got cold (green vs red), and I’m looking forward to the last 40 miles come Spring.

Along the inland segments, the wildlife is spectacular, and the map below shows some of my pictures from the first five segments (click on the ’s). If you’re just looking for a relaxing paddle, I’d recommend Columbia Woods or the Jackson Park Lagoon, both of which have excellent wildlife and no large crafts to compete with.

Few access points are included along the lakefront, since the beaches are "fairly obvious." Please mind the aeration points / hazards. They are somewhat invisible and truly scary, as they can substantially reduce buoyancy. Base map data © OpenStreetMap contributors, CC-BY-SA; layers by CARTO. Map data and photos © 2021 James Saxon.

Hyde Park to Lincoln Park

I put in at Promontory Point; since the beach was closed, I used the rocks. One interesting landmark on the way out of Hyde Park is the century-old shipwreck of the Silver Spray on Morgan Shoal / 48th St. It’s hard to find from the water, but I think I did; then again, when I circled for a closer look, I couldn’t find it again.

I rested at the Adler Planetarium and then cut into Monroe Harbor instead of going all the way around Navy Pier which felt a little too far out for me. In retrospect, it would have probably been easier to go around the pier: it is within the harbor’s breakwaters and no further than the Montrose Pier, for instance. But I didn’t. Staying within the harbor required me to portage half a mile from Rulland Grove to the Ohio Street Beach. From there, it was a quick loop around North Avenue Beach and to Diversey Harbor. It was only upon entering the South Lagoon by Lincoln Park Zoo, that I saw any other paddlers.

On the whole, it was interesting to see how “most” Chicago boaters experience the Lake, namely, with gas and booze. As on the canal segments, oblivious pilots and big wakes were occasionally nervewracking. The view of the city from Monroe Harbor was awesome — almost modern Venetian!? — but there was not much in the way of wildlife.

Lincoln Park to Wilmette

I got in at Diversey Harbor and got out at Gillson Park in Wilmette, just North of the Bahá’í House of Worship. Basically, I rounded Montrose Harbor and then made a bee-line for Northwestern University. Because I was about a half mile out, there were few birds and I had to mind the waves most of the time.

South to 136th Street

This was a fascinating segment, through Calumet Harbor down to the Thomas O’Brien Lock at 136th Street.

I cut directly from Promontory Point to Rainbow Beach and then Park 566. I lifted the kayak over the Calumet Harbor Pier, and then turned in to the Calumet River. This is the site of the Blues Brothers Bridge (South Ewing) and the Calumet Fisheries, and I actually saw the drawbridge rise (just enough for a boat to slip by!). The Norfolk Southern rail bridge and the Chicago Skyway are breathtaking from below. The 100th and 106th St Bridges were just renovated and they look great: they are classic bascule bridges with striking roofs on the tender buildings. At that point, the route got heavily industrial; this was something of an epiphany (here’s the shipping!) but it eventually got a little monotonous.

When the Calumet River forks to Lake Calumet and the Little Calumet River, I turned South, went through the Locks (!) and got out by Sunset Bay Marina.

The Cal Sag Channel

I put in at 136th Street, though I had originally intended to start from Beaubien Woods. The last official access heading west is at Worth, but I got out at Willow Springs Road. The bank under the bridge comes down to the water, and it is used for fishing. There is a well-trodden path that runs directly to the adjacent parking at Saganashkee Slough. There are other places where one might put out (as I later found), but not with easy access for a car.

The wildlife on this segment was great — lots of egrets, herons, and smaller birds. It was therefore somewhat distressing to see signs from the water district (MWRD) that all human contact with the water was inadvisable. There is also a 10-year old article in grist on the history and ecology of the Calumet River (tl;dr it is dirty). There is also a certain amount of Black history down here. I was first aware of Altgeld Homes as one of the sites to which residents of Cabrini Green were relocated, when that development was demolished. There was also a stop on the underground railroad at this site. Robbins, Illinois (half-way along the trek) is an early Black suburb with an influential history in early Black aviation (in particular). OpenLands produced a story map for their black history trail.

There was a lot of powered pleasure craft on the water (on a weekend), but I saw just one (magnificent) barge.

The Des Plaines River

This was probably the most enjoyable segment yet, thanks to abundant water fowl and an almost-complete absence of larger boats (or indeed, of any boats). I put in at Ottawa Woods (by Historic Route 66, as they emphasize).

The first part of the trip ran south towards the Stevenson Expressway, with numerous herons, egrets, cormorants, ducks, and a flock of geese. The river then runs alongside the Stevenson for 3.5 (loud) miles. The birds were clearly accustomed to the highway noise, and were quite skittish with my presence. The (thin) green barrier was enough that, from the River, one felt in wilderness despite the noise. An impressive feature of this segment (though not one visible from the River) is the McCook Reservoir. The 3.5 billion-gallon, billion-dollar component of the massive Tunnel and Reservoir Plan (TARP) holds sewage and run-off to prevent flooding and allow treatment facilities to catch up. The reservoir is sandwiched between the Stevenson and the Chicago Sanitary and Ship Canal (CSSC).

Shortly after the Stevenson cuts west is the Santa Fe Prairie, with a rare and interesting (though tiny) example of gravel prairie as well as a bright red caboose. From there on, especially after passing I-294, things got quieter. I had hoped to portage over the Centennial Trail to the CSSC, but a biker advised me against the high walls of the canal. The part of the trip in Columbia Woods, was the most-pleasant yet of my loop, with many cormorants. The State and Forest Preserve District of Cook County have been removing dams both on the Des Plaines and more broadly, improving the fish and bird habitats. (Although north of my path that day.)

I got out at Kingery Highway and portaged a third of a mile to get back in on the CSSC. I rounded the SEPA plant and little monument at Full Circle Terminal. I should not have gotten back on, as twilight had nearly fallen. I did not anticipate how quickly it would get truly dark, and I found myself more than 3 miles (about an hour) from my planned exit at Willow Springs Road. I therefore negotiated a tenuous, dark, obstructed, ultimately steep exit up the I&M (Illinois and Michigan) Canal at Grant Rd. This was stupid. Don’t be in the water at night.

Other Resources

I should also confess that I complained unfairly about the inadequacy of wild spaces near Chicago, when I moved. Though the city is definitely deficient in mountains, it was a huge blessing to find the OpenLands map of outdoor recreation in Chicagoland — both on water and land. I found their Paddle Illinois Water Trails resource after beginning the project, and it was a huge help, though the map is busted. They also have have an outstanding story map for their African American Heritage Water Trail, starting from Beaubien Woods. Friends of the Chicago River also has a map, though it is less-oriented to paddlers. The City also has a map from around 2012.

Several of these resources note the particular dangers of aeration stations, which create turbulence while reducing buoyancy (of both boats and people!). Since these hazards may not be immediately obvious, they can be dangerous for paddlers and I have noted their locations on the map.