During the second wave of the COVID-19 pandemic, my parents had to take a business trip to Chicago, a city on lockdown. They generously invited me along, and I am sitting on the plane ride home at the moment. Traveling on a plane was a huge change from what I am used to. The airports contained less people, the flights weren't even half full, and the mask requirements were the most strict here, probably because everyone is stuck breathing the same air for hours at 35,000 feet high. Security was a lot easier to get through though, so that was a win for me.
The city itself was still busy. I feel like no city, or it's people, ever slow down. Hundreds of people looked like they were on a mission, speed walking everywhere. Masks were mandated, even on sidewalks, and there were no restaurants offering indoor dining. I don't mind sitting outside at a place normally. However, it is not an ideal situation when it is 30 degrees outside. Shopping was still open and the designer stores were flooded with people. I think these instances were a little contradictory to each other, but I guess it's not my place to say.
The locals must be aliens of some sort because some people were wearing t-shirts while I was wrapped up like I was in the Arctic.
I don't think that the lockdown was too enforced as to where I could not enjoy my trip. Although, I did get tired of eating takeout food in my hotel room with my parents who I normally see once a month. That was a little too close contact from what I am used to now. If you can travel safely, I recommend buying that cheap plane ticket and go to your next destination.