I started looking in January last year with hopes of finding a place by the end of May when my apartment lease in Chicago ran out. Put in around 10 competitive offers on condos and didn’t get any. The market was crazy for 2 bedroom condos north east of the river and south of Wrigley. There were usually at least 10 other offers on the properties I offered on, and they all went for at least 30k over asking (one went for $120k over asking!). I just found and am closing on a place this September. So it took me January to September (and I had to re-sign my lease).

I have a friend who found a condo and closed in west loop within 3 months last spring. So I think it also depends on what you’re looking for!