There is a lot of varying information on oxygen creation from plantlife, mostly because the definition of 'tree' can vary so much. Environment canada suggests 2 mature trees produces enough oxygen to let a family of 4 live, while the new york times puts the figure at an acre of trees will support around 18 people. It also varies by species of tree and age, so it's hard to give firm numbers.
Using the 18 people per acre and 640 acres per square mile, you get around 11k people that can live off of 1 square mile of forest...which is actually around the same population density of chicago. Of course the trees will be competing with people for space, but if you could completely forest over all of chicago, the people there could maintain their oxygen supplies. I imagine if 1 half of the square mile was forest and the other half was city and humans, you could have 5000 people in a square mile breathing off of what the trees create.
Though it's very important to point out that we use oxygen in many other manners...combustion at it's core is consuming oxygen, and so does any of the meat products that we raise and consume. You'll have to have a very 'green' society to make this work...otherwise the population density of your city gets very low.