I've also squeezed an An-12 under the Eiffel Tower for a giggle

Take off from O'hare in any aircraft, fly to meigs, touch and go on runway 36, then fly on your side through the radio masts atop the skyscraper in front of you!
Smaller aircraft can take off from Meigs, and fly through the radio masts right away.
HINT: It looks better with Smoke on.
2) Take a big plane and land at a small airport. For example, there's this little airport near here (Peprell, MA, USA) that's a challenge for small GA type planes as the runway is short and the approach requires you to thread the needle between some hills and trees. It's even more of a challenge in a 737.
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