It was only my DD who actually had to do "Chicago Math", as DS was only in pre-school at the time. This was grade 2, but much like the original problem in this thread, the homework problems were very convoluted and just didn't make sense. What happened at homework time was tears and frustration on DD's part, and me phoning every teacher friend I knew asking them WTH is this even asking!?! Unfortunately for me, but fortunately for my teacher friends in other states and another country, they were NOT using this curriculum and didn't have a clue.
Between that and "teaching to the test"/standardized test prep, it got to the point that DD was in tears every morning, not wanting to go to school.
Homeschooling was much easier, compared to that.