Winthrop Harbor → Navy Pier, Chicago
September 29, 2026
Distance: ~36 nautical miles
Waterway / State: Lake Michigan — Illinois
Locks: 0 | 0 total so far
Notable: Heavy fog early, then nearly flat water and the Chicago skyline gradually appearing through the haze.
The Trip
We left Winthrop Harbor heading for Chicago in some of the thickest fog we had seen so far.
The fog came and went along the route—clearer in some areas and very thick in others—but the water itself could hardly have been better. We started with less than a foot of waves, and before long the lake was almost completely calm.
It made for a pretty surreal trip.
As we got closer to Chicago, the skyline gradually began appearing in the distance through the remaining haze. We were able to get some great pictures of the buildings as silhouettes before the fog finally burned off and the city came fully into view.
Coming into Chicago by boat was very cool.
We worked our way around to Navy Pier Marina and found our slip almost directly beside the Ferris wheel, with the Chicago skyline in front of us. It was one of those arrivals where you immediately knew the location itself was going to be part of the experience.
The Experience
Navy Pier Marina was one of the nicest and most convenient marinas we had stayed at so far. It ran right alongside Navy Pier and had a lounge, laundry facilities and a small gift shop, while everything on the pier was just steps away.
Once we were settled, we each went out for a little exploring. Julie went for a run, while Greg walked around Navy Pier, into the city for a few blocks and over toward the beach.
Later that afternoon, we met up with Conner Mahern, who lives in Chicago and works with us at aFit. Conner came down to the marina, we gave him a tour of Breaking Awave, and then the three of us headed out for dinner.
We found a very nice Japanese restaurant, had some great sushi and spent the evening catching up with Conner about how things were going with work. One discovery from dinner that we definitely remembered was Wandering Poet sake.
It was a pretty great day: an easy ride once the fog started clearing, one of the best arrival views we had seen yet, and an evening with someone from home.
At the Helm
The waves weren’t the challenge on this leg.
Visibility was.
Leaving Winthrop Harbor in thick fog was another reminder that good boating conditions aren’t only about wind and wave height. The lake could be almost perfectly flat and still require plenty of attention when we couldn’t see very far ahead.
Fortunately, the fog gradually improved as we moved south, and by the time we reached Chicago we had sunshine and a clear enough view to really enjoy the approach.
The day also gave us another first: approaching a major city from the water instead of by road.
Seeing Chicago slowly emerge ahead of us was very different from simply driving into town—and definitely one of the more memorable arrivals of the trip so far.
Today’s Route
[Nebo route visual]
Today in Pictures
[Fog leaving Winthrop Harbor, calm Lake Michigan, Chicago skyline emerging through the haze, Navy Pier approach, Breaking Awave beside the Ferris wheel, city/beach walk, Conner aboard, evening in Chicago]