What's the best angle of the skyline to show off its true size?

From the side and trim the bush

View from Adler Planetarium area is nice.

Right after the bush is trimmed.

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Planetarium is your best bet. Or hitch a ride with r/chicagohelicopters and shoot from the east side of Navy Pier during one of their night missions.

From going north on 294 as it goes up about 60 feet in Schiller park. You can see the whole real city instead of just the facade on the lake front. The sunrise from that view is amazing.

Boat or Planetarium. Planetarium outside is much more free.

I've always really liked Promontory Point down in Hyde Park(and walking distance from Museum of Science and Industry), for a lakefront place where you see a lot of the downtown well. It juts out further east, than other points along the south side lakefront. For points north, I always liked the southern point of Montrose Harbor, and also the pier to the south and east of North Ave Beach(sigh, the lone thing that I'd visit the area by that beach for).

From the west, go to the bridge over both platforms of the Ashland Green and Pink Line 'L stop. Look east and you'll get an amazing view from the north to south of the skyline, especially at night.

You're all a riot...