I love visiting Chicago and was thinking about taking my Mini SE. I saw this video which outlines that if you want to fly to the top of a building and that building is over 400 feet it is allowed. I think it'd be cool to get a shot of people in the observation deck of Willis tower and then pan around to the skyline. Have any of you done something similar?

Hello there. Good day and thank you for reaching out.  I hope that our fellow DJI co pilots can give out the best recommendation where to fly in the Chicago, Illinois area and with regards to this matter. In addition, I will post a DJI link where you can check some places in Chicago, Illinois where in you can fly your DJI freely or if the said location is a No Fly Zone ( NFZ ). Thank you and have a nice day.

https://www.dji.com/flysafe/geo-map