We bought our house in 2021, near the beginning of the big housing price surge in Chicago. It’s strange that time ended up being the best time to buy in the city because conditions were right for sales to occur, even if they were fast and highly competitive. We mortgage rates at 8% I’m not sure economists expected prices to stay high while inventory shrank. Second order effects are unpredictable at times. Talking to friends who want to move within the city, usually to be closer to school, most seem to have given up on that happening this year. Houses in Chicago tend to fall into two camps: gut rehab and teardowns that are selling for $2M, or houses in bad shape will likely need to be a complete teardown. There just aren’t any move-in ready homes for sale right now.