Senior & Downsizing Moves in Chicago, IL

Downsizing paced to what the family actually needs, coordinated with whoever's helping from near or far.

This goes directly to Michelle, no forwarding, no queue — she or Desmond calls back the same day to get your Chicago move on the calendar and flag anything worth a closer look at the walkthrough.

ProMover AMSA Certified
BBB Accredited A+ Rating
US DOT FMCSA Registered
Fully Insured Cargo Protected
IAM Member Intl. Movers Assn.
IL ICC Licensed Illinois Commerce Comm.

A downsizing move rarely runs on the same clock as a standard move, and Checkmate doesn’t try to force it onto one. Some families need the whole process spread across two or three visits — sorting one weekend, packing the next, moving day after that — and some need it handled in a single day because that’s what works for the person moving. Michelle Torres schedules around whichever pace the family actually needs instead of defaulting to a one-day script because that’s how the calendar prefers it.

Coordination with family members is usually part of the job in a way it isn’t on other moves — an adult child in another state making the calls, a sibling handling logistics locally, sometimes a facility with its own move-in windows. Jamal Whitfield walks through what’s going to a smaller space, what’s going to family members, and what’s going into short-term storage in the meantime, and works out a load order and a timeline around all three before crew day, not during it.

The crew pace on-site matches the plan set at the walkthrough — not rushed, not padded with unnecessary hours, just the amount of time the specific move actually needs. Basic released-value protection is included on every job, and the same hourly local rates apply.

  • Move paced to the family’s timeline, not a standard one-day default
  • Coordination with out-of-town or local family members
  • Sorting between new home, family members, and short-term storage planned in advance
  • Standard hourly local rates, no separate markup

What This Service Includes

  • Move paced across one visit or several, by family preference
  • Coordination with family members near and far
  • Sorting plan for new home, family, and storage set in advance
  • Same hourly local rates as any Checkmate move
  • Basic released-value protection included

What This Service Costs

Crew size sets your hourly rate — $145/hr for two movers, $185/hr for three, $225/hr for four — or if you'd rather book off a written number, Jamal can walk the place first and price it before move day

That hourly rate covers the truck, dollies, furniture pads, and shrink wrap — nothing billed separately: $145 for two movers, $185 for three, $225 for four, and $50/hr for each mover beyond that. A $175 deposit holds your date and comes straight off the final invoice. Every job includes basic released-value protection at no added cost; for anyone who wants more coverage on a specific item, Michelle sets up a full-value quote when she books your date.

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What Chicago Customers Say About This Service

Amanda Lindley
Amanda Lindley
Naperville · Google
★★★★★

“Eddy and Micael were super efficient, professional, and helpful. We needed furniture moved out of one room in order to repair flooring and they moved everything in less than an hour.”

Jason Birn
Jason Birn
Chicago · Google
★★★★★

“Romance and team responsible for my move. They were extremely helpful and happy to do anything and everything asked. They all went above and beyond. Thank you Romance and Team!”

Daniel O'Shea
Daniel O'Shea
Oak Park · Google
★★★★★

“Issac Hernandez and crew were absolutely PHENOMENAL!!! Got us moved in record time and budget friendly. Everything came in just the way it left. Would ABSOLUTELY hire again!!!”

Questions About This Service

Can a downsizing move be spread across more than one day?
Yes — some families sort one visit, pack the next, and move on a third; Michelle Torres schedules around the pace that works for the family, not a fixed one-day script.
Do you coordinate with family members who live elsewhere?
Yes, coordinating with an out-of-town adult child or a local sibling handling logistics is a routine part of these moves.
Can items be split between a new home, family members, and storage?
Yes — Jamal Whitfield works out the split and the load order for all three at the walkthrough, before crew day.
Is there a separate rate for senior or downsizing moves?
No, the same hourly local rates apply — $145 to $225/hr depending on crew size.
What Sets Checkmate Movers Apart Around Chicago

Here’s What Checkmate Movers Does Differently Than Most Movers Around Chicago

Licensed With Illinois’s Commerce Commission — Not Just A Line On The Website

Household movers working Chicago and the surrounding Cook, DuPage, and Lake County suburbs have to carry ICC registration through the Illinois Commerce Commission; Checkmate Movers keeps it current every year, no lapses. The moment a job crosses the state line into Wisconsin, Indiana, or beyond, it's US DOT and MC authority that's covering the move instead.

You Pick Your Coverage Before The Truck Ever Loads

Basic released-value protection comes standard on every job at no cost. Ask Jamal about full-value coverage at your walkthrough if you'd rather have the higher payout ceiling You hear both options once, at the estimate — nobody's pitching an upgrade halfway down your stairwell with a dresser on their shoulder.

The Walkthrough Builds A Plan, Not Just A Price

Desmond spent eight years running crews for a big-box moving franchise where a couch could get carried up three flights twice because nobody had worked out the order first. At Checkmate Movers, Jamal maps furniture placement, load order, and building access at the in-home estimate — elevator windows, stairwell turns, tight doorways — so the crew walks in with a plan already set instead of working one out in the truck.

All Eighteen Of Us Are On Payroll, Not A Rotating Bench

Eighteen people are on payroll at Checkmate Movers, fourteen of them movers running nine trucks — no day-labor crews brought in when a week gets busy, no subcontractors filling out a truck. Desmond built it that way on purpose: a plan only holds up if the crew executing it actually works for the company that wrote it.

Every Move Planned Before The First Box Does.

Furniture placement, load order, and building access get worked out at the walkthrough, before anyone touches a box on moving day. Desmond Hale started Checkmate Movers in 2013 after eight years running crews for a franchise that never planned a job in advance, and watched the same couch get carried up the same stairs twice because of it.

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