Moving in Chicago is its own discipline. Between high-rise loading docks, ward-issued parking permits, alley access that a 26-foot truck cannot always use, and vintage walk-ups with staircases built before sectionals existed, the preparation matters as much as the muscle on move day.
This checklist is organized by how far out you are. Work it in order and the actual move becomes the easy part.
The checklist below assumes a city move with building rules attached. If you are heading out to the suburbs instead, the same sequence works for Evanston and Park Ridge — only the parking and elevator steps change.
Four to six weeks out: dates, quotes, and building rules
Set the date first. Chicago's rental market turns over on the first and last days of the month, which concentrates demand into a handful of days and makes the last summer Saturday the hardest slot in the city to book. If you have flexibility, a mid-month weekday is cheaper, calmer, and easier to staff well.
Then get quotes. Any estimate produced without questions about your floor, elevator, and parking is a placeholder rather than a price — our cost breakdown explains why access drives the number more than square footage does.
Finally, request the move-in and move-out rules from both buildings in writing. Managed buildings downtown, in River North, Streeterville, the South Loop, and along the North Side lakefront almost always have them, and they are not negotiable on the day.
Certificates of insurance and freight elevators
Most Chicago buildings above a certain size require a certificate of insurance from your mover naming the building owner and management company as additional insureds. The mover issues it, but the tenant usually has to request it and route it to management, and approval commonly takes several business days.
The freight elevator is the other half. Reservations are typically a fixed window — often ninety minutes or two hours — and weekend and month-end windows fill weeks in advance. Take the earliest slot available; morning windows rarely slip, while afternoon windows absorb every delay ahead of them.
A missing COI is the most common reason a move is turned away at the door, and the crew still bills for the day. This one task deserves a calendar reminder.
If you're in a walk-up
Vintage two- and three-flats across Lincoln Park, Logan Square, Pilsen, and Rogers Park come with narrow staircases, tight landings, and doorways framed before modern furniture. Measure the sofa, the mattress, and any armoire against the narrowest turn.
Tell your mover the floor and the stair situation during the estimate. Stairs are not a problem; unannounced stairs are, because they change crew size and the time the job takes.
Three weeks out: parking permits
If either address is street-parked in the City of Chicago, request a temporary no-parking permit through the Department of Finance for your ward and post the signs the required number of hours in advance. Without it, the truck may end up a block away, and on an hourly move every trip to it is billed.
Even with a permit, occupied spaces happen. Park your own car in the spot the night before if you can, and have the permit paperwork on hand — it is what lets you resolve a dispute quickly rather than at length.
Check the alley too. Many buildings have rear access that is faster than the front, and many alleys will not accommodate a full-size truck. Your mover will want to know which is true at your address.
Two to three weeks out: pack from least-used to most-used
Start with storage, decor, books, and off-season clothing. Save the kitchen, bathroom, and bedroom for the final days. Label every box on two adjacent sides with the destination room and a one-line contents note, because boxes get stacked and top labels disappear.
Pack heavy items in small boxes and light bulk in large ones. Fill every void. Plates ride on edge, wrapped individually. Our fragile packing guide covers the details that prevent the most common breakages.
If finishing on time is genuinely in doubt, book help now rather than discovering the gap on move morning. Half-packed is the most expensive state to be in, since a moving crew ends up doing packing work at moving rates. Packing and unpacking is cheaper as a plan than as an improvisation.
One week out: utilities, confirmations, and logistics
Transfer electricity, gas, internet, and water with a one-day overlap at both ends. File the USPS change of address. Update your license, insurance, and bank. Cancel or transfer local services.
Re-confirm with your mover: date, arrival window, crew size, both addresses, elevator reservation, and COI status. Confirm the loading dock hours with building management one more time.
Arrange care for kids and pets, and plan where the car goes. A move day where you are not also managing a toddler and a nervous dog is a different experience entirely.
Move day: what to keep with you
Keep a suitcase and one marked box off the truck: keys, IDs, documents, medications, chargers, a change of clothes, basic tools, paper towels, and toilet paper. Designate a 'do not load' zone by the door so nothing wanders onto the truck.
Walk the crew through the home when they arrive. Point out the specialty items, the stairs, the door that sticks, and anything not going. Five minutes there saves an hour later.
At the destination, direct furniture placement as items come off the truck instead of staging everything in one room. Make the beds before dark.
Neighborhood realities worth knowing
Downtown and the near neighborhoods — the Loop, River North, Streeterville, the South Loop, West Loop — are dock-and-freight-elevator moves. Expect a reserved window, a COI, sometimes a security desk that needs advance notice of every crew member's name, and occasionally a requirement to use a specific service entrance.
The bungalow belt and the vintage neighborhoods — Portage Park, Irving Park, Avondale, Bridgeport — are staircase and alley moves. Access is usually easier than downtown, but the staircases are narrower and older, and the alley may or may not take a 26-foot truck.
Lakefront high-rises in Edgewater, Uptown, and Lakeview combine both problems: a freight elevator reservation plus street parking that is genuinely contested. These are the addresses where a permit matters most.
If you're moving to the suburbs
A move from a city condo to a DuPage house is usually easier on the unload than the load: a driveway, a garage, and no elevator. Budget your time and crew size around the city end, which is where the hours go.
Check the destination HOA rules anyway. Newer subdivisions in Naperville, Warrenville, and Glendale Heights sometimes restrict truck staging, weekend hours, or dumpster placement.
City-specific realities worth planning around
Winter adds salt, slush, and short days — clear and salt every path the night before, and expect a 4:30 p.m. sunset in January. Our winter moving guide covers the rest.
Summer adds traffic and heat. Loading on Lake Shore Drive-adjacent streets at rush hour is slower than the map suggests, and a 90-degree day in a fourth-floor walk-up changes the pace of any crew, professional or otherwise.
Month-end means you are one of several moves in your building that day. Being first on the dock is worth rearranging your schedule for. If you want that slot, request a quote early — our Chicago crews book the popular dates well ahead.