Everyone plans around May. Then the last weekend of September arrives and half of Lakeview is double-parked with a couch on the sidewalk. Chicago's fall lease flip is real — smaller than May's, concentrated enough to book out every truck in sight. Here's the junk playbook: whole-unit clears from $241, booked against the walkthrough, same flat prices as any quiet week.
One photo — flat quote in seconds, slot guaranteed
Upload a Photo & Get Quote →| What's going | Flat price |
|---|---|
| Studio's worth — quarter truck | $241 |
| 1-bed — half truck | $431 |
| Furnished 2-bed — full truck | $732 |
| Mattress — twin / queen / king | $82 / $103 / $114 |
| Sofa / futon | $126 / $103 |
| Desk / bookshelf / office chair | $83 / $72 / $61 |
| Bagged load — 10 bags / box lots | $132 / $31 each |
$75 minimum. Back stairs and freight elevators included; itemized receipt for the deposit file; donation-grade pieces routed to donation. The scarce thing in flip week is the calendar, never the price.
The turnover math is unforgiving — the old lease ends, the new one starts, and whatever the tenant left is standing in the gap. Left-behind units clear at the same flat truck-fill rates, photographed empty as each finishes, one invoice for blocks — scheduled into the gap so the incoming lease starts on time. Off-peak, a single unit typically turns within 24 hours of the photo; in flip week, the block reservation is what guarantees it.
Chicago leases cluster on two start dates — May 1 and October 1 — so the city gets two turnover waves a year. October's is the quieter sibling: smaller than May's but concentrated enough that the last weekend of September books moving trucks, freight elevators, and junk-removal windows all at once, and it catches people who assume moving season ended in summer.
A few days ahead — the Sept 27–Oct 2 windows are the fall's busiest and fill in order. Book the clear against the walkthrough, not the moving day: after the boxes leave, before the keys go back. Same flat prices as any week (whole-unit clears $241–$732, mattresses $82–$114) — no seasonal surcharge, just calendar scarcity.
The flip is exactly when the alley fails: every legitimate set-out spot is already claimed by neighbors doing the same math, ward collection doesn't accelerate for moving season, and a pile that sits into your successor's tenancy is a complaint with your name on it. Landlords also photograph left-behinds during walkthroughs and deduct at their hauler's rate — the receipted clear beats the deduction.
Between-tenant clears: the left-behind unit photographed, cleared at flat truck-fill rates ($241 lightly left-behind to $732 full abandonment), each unit photographed empty, one invoice for multi-unit blocks — scheduled in the Sept 30/Oct 1 gap so the incoming lease starts on time.