Apartment & Condo Moving in Chicago, IL

Freight windows, stairwells, and tight turns get mapped at the walkthrough — not discovered with a dresser stuck in the doorway.

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.

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Apartment and condo moves in Chicago live or die on timing, not muscle. A high-rise with one freight elevator might give a building a four-hour window on a Saturday morning before the next tenant’s slot opens, and a third-floor walk-up doesn’t have an elevator at all — just a stairwell that turns twice before it reaches the street. Checkmate plans around both at the walkthrough, before the move ever gets booked on the calendar.

Jamal Whitfield maps the actual route a couch or a dresser has to take out of a specific unit: which stairwell is wider, whether the freight elevator fits a mattress flat or has to go in on its side, and how many trips a crew can realistically make inside a two-hour freight window before the clock runs out and the job spills into overtime. That routing gets worked out before crew day, so the crew isn’t discovering a tight stairwell turn for the first time with a dresser wedged in it.

Elevator buildings, walk-ups, and everything in between get the same hourly local rates as any other Checkmate move — $145 to $225/hr depending on crew size — and the same basic released-value protection included at no charge. What changes is the routing plan, and that gets worked out in advance so freight-window time doesn’t get burned re-figuring the stairwell on the spot.

  • Freight elevator windows scheduled and mapped in advance
  • Walk-up stairwell routes worked out at the walkthrough
  • Furniture measured against tight turns and doorways ahead of time
  • Same hourly rates as any local move, no elevator surprise sprung on move day

What This Service Includes

  • Freight elevator window scheduled ahead of move day
  • Walk-up stairwell route mapped at the walkthrough
  • Furniture measured against doorways and turns in advance
  • Same hourly rates for elevator buildings and walk-ups
  • Basic released-value protection included free

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

How do you handle freight elevator buildings?
The freight window gets scheduled and the route through the building mapped at the walkthrough, so the crew isn't figuring out elevator logistics on move day.
What about walk-up buildings with no elevator?
Jamal Whitfield walks the stairwell in advance and plans the route — which turns are tightest, what has to go up or down sideways — before crew day.
Is there an extra charge for elevator or walk-up buildings?
No — the same hourly local rates apply. What changes is the routing plan, not the price structure.
Do I need to reserve the building elevator myself?
Coordinating the freight window is part of the planning conversation with Jamal Whitfield during the walkthrough.
Eight Years Running Crews For A Franchise Taught Desmond What Planning Actually Prevents

One Rule Since Day One: Plan The Move Like A Chess Game, Not An Improv Show

“I spent eight years running crews for a big-box moving franchise, and jobs went sideways more than they should have — a couch carried up three flights twice because nobody had worked out the order first, a truck getting repacked on the sidewalk after it was already loaded wrong. I started keeping my own notes on load order and room sequencing, even on jobs that weren't mine, because watching it happen bothered me more than it should have. I started Checkmate Movers in 2013 on the idea that a move gets planned like a chess game — furniture placement, load order, and building access worked out before anyone touches a box, not improvised in the doorway.”
Desmond Hale
Owner · Checkmate Movers

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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