Samantha Caballero cannot remember the last time she slept well. Some nights she nods off in a chair. She has slouched in the front seat of her brother’s station wagon or huddled between boxes in her mother’s storage unit. Sometimes she squeezes onto a friend’s extra bed with five of her six children.

There are seven of them: Six children. One mother. No home.

On most days, when she wakes at 6 a.m. from a half-sleep, Ms. Caballero must get her 12-year-old daughter, Lajuanese, and her three boys, Jovany, 11; Deangelo, 6; and Jaden, 3; ready for school. She makes sure they have school assignments in their book bags, toothbrushes and a change of clothes; the family may change addresses during the day.

As with any large family, everything requires planning. With her two youngest, Devonta, 4 months, and Samantha, 3, Ms. Caballero spends her day navigating a maze of bureaucracies: cash assistance, food stamps, Social Security, schools, shelters and health care.

Former Mayor Richard M. Daley’s 10-year plan to end homelessness focused on the chronically homeless, substance abusers and the disabled. But nine years later, many young people and families are still on the streets. Mayor Rahm Emanuel plans to update the plan early next year.