A young professional is tired of spending money on rent and has her sights set on a historic walk-up condo in Chicago. She's bringing her analytical ex-boyfriend on the search, and he thinks she should consider a newer, high-rise condo. S228E03

A young couple looks to buy their first home together after relocating for work to Illinois. He's looking for a newer ranch-style house with a big yard, but she's hoping for an older Craftsman with unique details. S228E08