While we went on the 4PM tour, I would anticipate that the 8PM tour is safe as well. It’s all in well-lit, populated areas of the city and our guide was very knowledgeable of the area. However, it will likely be cold - as long as you bundle up, you should be fine.

It’s a full 2 hrs of walking at a decent pace. There is a 20min break at a hotel and that is all. I would be hesitant honestly.

It is full price for all.

We all three enjoyed the tour. The guide gave us many stories about Chicago that we didn’t know and took us to several areas that we hadn’t walked to. We thought it was worth the money.

no it doesn't

Meeting place is outside of the Hoyt's sign at the Wyndham Hotel. Time depends on the schedule you chose. They run (I think) four guided tours in a day. The last tour starts at 8PM. Hope this helped.