The Chicago Skyline at 1,500 Feet

Most people see the Chicago skyline from the ground, or from 30,000 feet on the way somewhere else.

There’s a third option. You can fly the lakefront at low altitude, right alongside the buildings, and watch the whole downtown go by at eye level.

That was the last leg of our Toronto weekend.

Leaving Detroit

After clearing customs in Detroit, we had one leg left — and it started the way big airports always start for a small airplane.

Waiting our turn behind the giants.

737s on one side, us on the other. A Cessna 210 feels very small on a taxiway built for jets. But the sequencing is the same, the tower talks to you the same, and eventually you get the same runway everyone else does.

Across the Bottom of Lake Michigan

Detroit to Chicago is a straight shot across the bottom of the lake.

Open water again — the same lake we’d crossed on the way out, three days and a whole trip earlier. It felt like a bookend.

The Skyline Appears

You can see Chicago from a long way out. A cluster of towers standing alone against the water, growing in the windshield by the second.

Then we turned up the lakefront and dropped down to 1,500 feet.

Flying the Lakefront

Here’s what photographs never capture: from up there, the buildings don’t shrink.

They stay tall. They stay right beside you.

Navy Pier passed below the wing. The beaches were packed. Sailboats scattered across the water, and the whole downtown skyline standing at eye level — the Willis Tower, the Hancock, close enough that it felt like you could reach out.

It lasted a few minutes. I’ll remember it for a lot longer than that.

The Part Nobody Puts in the Highlight Reel

Past the skyline, the city gave way to farmland and the last stretch home to Minneapolis.

And that’s when the headwind found us.

Between circling Niagara, detouring down the Chicago lakefront, and now a stiff wind pushing back the entire way, this turned into easily the longest leg of the trip. Flying into a headwind is exactly what it sounds like — the airplane works harder, the ground crawls by slower, and a short hop becomes a long one.

Nobody complained. We were all still somewhere over Niagara Falls in our heads.

Home at Flying Cloud

And then, finally — Flying Cloud.

Same runway we’d left three days earlier. But between then and now: a night landing in downtown Toronto, two laps around Niagara Falls, a customs officer at our wing in Detroit, and the Chicago skyline at 1,500 feet.

One small airplane. Five people. One very full weekend.

Why the Journey Is the Trip

Here’s the thing about flying yourself somewhere: the flight isn’t the boring part you endure to get to the good part.

The flight is the good part.

We could have gone direct and been home hours earlier. Instead we took the long way — over a waterfall and past a skyline — and turned a trip home into the best flying of the weekend.

That’s the whole reason I keep doing this.

Watch the Full Video

The final leg — Detroit, the Chicago lakefront, and the long headwind home — is up on YouTube. It’s the last of three videos covering the whole weekend.

Catch up on the rest of the trip:

Where should we fly next? Drop a suggestion in the comments — I read every one, and a few past trips have started exactly that way.

Blue skies and tailwinds.