September 22, 2026

Chicago to Heritage Harbor

Good news: the bridges cleared. After a few days waiting at Navy Pier Marina to see whether the stuck Amtrak bridge would get fixed, we got the all-clear to run downtown and start south on the rivers.

Two Days in Chicago First

Before we untied, we spent two full days on foot seeing the sights in the Windy City. Buckingham Fountain was running full blast, we fought the crowds at Cloud Gate (“the Bean”) in Millennium Park, and we found the statue of Captain George “Cap” Streeter — the eccentric squatter who gave Streeterville its name — tucked into a flower bed a block off the river.

At Cloud Gate

Buckingham Fountain

The Grant Park rose garden was still blooming, skyline right behind it, and along the lakefront the flower beds were full of monarchs staging for their migration south — fitting company, since we’re headed that way too.

Chicago Harbor Light, framed by the lakefront gardens

Walking the waterfront, we passed another marina down the way where two Portuguese Water Dogs had the right idea — sprawled out on the hull, not a care in the world.

Living the good life at a marina down the waterfront

Downtown by Water

With the bridges finally working, we ran the boat up the Chicago River through downtown — skyscrapers on both sides, the fog burning off over the skyline, Navy Pier’s Ferris wheel behind us as we came back in off the lake.

Chicago Harbor Light from the pilothouse, city behind it

The old pilings in the foreground are all that’s left of the original Navy Pier, with today’s Ferris wheel behind them

Running the river downtown

South Through the Canal

From there it was on to the Chicago Sanitary and Ship Canal, the man-made waterway that carries Great Loop traffic out of Lake Michigan and down toward the Illinois River. A couple of railroad lift bridges were up for us along the way — a relief, after worrying for days that one of them might not be.

Old timbers and chain at the base of one of the bridges

The canal is industrial and a little eerie in places — barge traffic, old boatyards, and a sign we don’t see back home warning of the electric fish barrier the Army Corps maintains here to keep invasive Asian carp out of Lake Michigan.

A reminder to keep up with maintenance — this one didn’t

We came through the spillway where the Cal-Sag Channel meets the Illinois Waterway, marked by a stone monument on a grassy point.

Where the Cal-Sag Channel meets the Illinois Waterway

We tied up for the night at Harborside Marina, mile marker 273.5, just before the Dresden Lock. Early the next morning a loaded barge tow went by, all lit up and throwing a spotlight ahead of it.

A tow passing Harborside Marina before sunrise

We were surprised how much wildlife we saw so close to the city — herons and egrets all along the banks, including this great blue heron who stood watch, unbothered by the traffic.

Heritage Harbor

We made it to Heritage Harbor Marina on the Illinois River, a favorite stop for Loopers heading south.

When getting our steps in today we came across a memorial bench honoring the marina’s longtime Harbor Master. We met him three years ago on our first Loop. He took the time to give us and other Loopers a presentation on what to expect as we headed south, and during that trip we exchanged several texts with him directly as we worked out safe anchorages along the way.

We had no idea that 3 years ago would be the last time Jeremy would give a presentation to Loopers.

It was a simple reminder of something we too easily forget: don’t take people, opportunities, or even ordinary moments for granted. We often assume there will always be another conversation, another visit, another opportunity to say thank you.

But we don’t know what God has planned or how much time we have with the people He puts in our lives. His providence is often something we only recognize looking back.

As we continue our journey south, we’re reminded to be grateful for the people we meet, the places we get to see, and the time we’ve been given. We may not understand where every turn is leading, but we can trust the One who does.

Don’t take today for granted. Be thankful. Love people well. And trust God’s providence, even when you can’t see the whole journey.

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