Especially in Chicago, September seems to be the beginning of a the “new year” for renting. The huge number of Chicago leases run through the end of September and this means that October 1 is usually the biggest moving day in the city. That also means that September is the month when it is, theoretically, easiest for fast-acting tenants to find a rental or quality landlords to find a tenant because so many leases are expiring at month’s end. Those new October leases and increased demand also bring increased rents with them.