Last year, I left work early and was going home on the L - so it was not crowded. I sat next to a family visiting Chicago - about 6 people various ages - and they were just riding the L to see various neighborhoods. This was on the Red Line but I think that taking the Brown Line would be more interesting - at least the ride around the loop. I had never thought of this but this family was having a great time - and it is pretty inexpensive. I had a great time pointing things out for them.