The best part about buying a home? Getting the keys!

The worst part about buying a home? Moving.

But as much as everyone hates the idea of moving, it requires more strategy and planning than you might think. 

We’re the Ben Lalez team, and we’ve helped so many families move across every corner of Chicago that we’ve learned exactly what works and what doesn’t when timing your move. We’re often asked, “What is the best day to move?” 

Let’s break down how to choose the perfect moving day to save you money and minimize stress.

Chicago’s Moving Seasons

If you already live in Chicago, you know that the real estate market has distinct seasonal patterns that affect both moving costs and convenience. Summer is typically the busiest moving season, with about 70% of moves happening between Memorial Day and Labor Day, but this means higher costs and more competition for moving services.

Want to know the two busiest moving days of the year in Chicago?

May 1st and October 1st.

It’s always been this way, and while these dates usually match up with lease turnovers and offer the most housing options, they also mean competing with other movers for elevators, parking spots, and moving services. In other words, it can get messy.

When To Schedule Your Move

If you’re flexible with your moving date, here are some insights to help you pick the best time to move.

Best Month

If you want the lowest moving costs and greatest negotiating power, aim to move in the winter months from December through February. Property managers are more likely to offer move-in specials or reduced rents during these slower months. 

Don’t stress out too much about moving in the harsh Chicago winters – professional movers are well-equipped to handle winter conditions, and you’ll have more scheduling flexibility.

Best Week Of The Month

Most leases end at the beginning/end of the month, so mid-month moves (between the 10th and the 20th) typically cost less than the end of the month or the beginning of the month. This timing avoids the rush of lease turnovers and gives you more negotiating power with moving companies. One important benefit is you’ll find better elevator availability in high-rise buildings during mid-month moves.

Best Day Of The Week

The best time to move during the week is from Tuesday through Thursday. Weekend moves will be more expensive due to high demand, while Monday moves often conflict with building maintenance schedules. On average, mid-week moves typically save you 10% to 20% on moving costs and offer more open time slots. Don’t forget to negotiate and ask for a discount!

Seasonal Moving Tips

Moving In The Summer

You’d think that moving in summer is the obvious and easy choice, but summer brings unique challenges to Chicago moves. The combination of peak season pricing and intense humidity means you’ll need to spend some time planning. While summer offers the most housing options, you’ll be competing with thousands of other movers, especially around popular areas like Lincoln Park and Lakeview where student turnover is high.

Here are some things to note about summer moves:

  • Book your moves at least 8 weeks in advance
  • Schedule early morning moves to escape the heat
  • Plan around major events like Lollapalooza and the Air & Water Show
  • Check construction projects that could affect your route
  • Expect to pay premium rates during these peak summer months

Moving In The Fall

Fall is a sweet spot when it comes to moving in Chicago. The weather is typically cooperative, and you’ll find a good balance between housing availability and competitive pricing. The shorter daylight hours become more noticeable by late October, which means what might have been a comfortable 6 pm finish in the summer could now mean unloading in darkness.

If you’re moving in the fall, consider this:

  • Watch weather forecasts closely for rain
  • Plan your timeline around shorter daylight hours
  • Consider school schedules if moving with children

Moving In The Winter

Winter moves in Chicago require extra planning but can help you save some money. We’ve seen clients save up to 30% on their moving costs during these months. The key is building flexibility into your timeline. Chicago winters are notoriously unpredictable, meaning one day might be a manageable 30 degrees, and the next day could bring a foot of snow.

Here is how you prepare for a winter move:

  • Ensure walkways are clear of snow and ice
  • Protect floors from salt and slush damage
  • Book moves during daylight hours
  • Have backup dates ready in case of severe weather
  • Consider mid-day moves for warmer temperatures

Moving In The Spring

Spring brings renewed energy to Chicago’s real estate market with its own set of unique challenges. Municipal street cleaning schedules resume, affecting parking in residential areas. Construction projects start up again, particularly around high-development areas in the city. The unpredictable spring weather can swing from late snow to heavy rain, requiring careful planning.

Here are some things to remember when moving in the spring:

  • Watch for rain forecasts and have waterproof covers
  • Check street cleaning schedules
  • Book early as moving companies start raising rates for peak season
  • Plan around spring break if moving with children

Best Times To Move For Different Property Types

High-Rise Buildings

The key to a successful and stress-free move in a high-rise building is understanding building policies and peak usage times. Most buildings restrict moving hours and require advance booking of freight elevators. We recommend:

  • Booking freight elevators at least two weeks ahead
  • Moving during off-peak hours (10 am through 4 pm)
  • Checking building rules about insurance and deposit requirements
  • Understanding loading dock time limits

Walk-Up Buildings

Chicago’s vintage walk-ups require special consideration. Moving into a third-floor unit takes much more time and effort than a first-floor apartment. You want to consider:

  • Extra time needed for stair moves
  • Narrow hallway navigation
  • Street parking availability
  • Weather impact on outdoor stairs

Single-Family Homes

While you’ll have more flexibility with timing, single-family home moves will also need some considerations:

  • Seasonal impacts on street parking
  • Neighborhood street cleaning schedules
  • Access points for moving trucks
  • Yard and landscaping protection

Cost-Saving Moving Strategies

If you spend some time planning carefully, you can significantly reduce your moving costs. Beyond choosing off-peak seasons and mid-week dates, consider these sound strategies:

  • The longer ahead you book, the more you can negotiate better rates
  • Compare multiple quotes and watch for seasonal promotions
  • Consider a hybrid approach by moving smaller items yourself
  • Get insurance through existing policies when possible
  • Have everything packed before the movers arrive
  • Ask about multi-service discounts

Putting Everything Together

If you want to have the perfect moving day, you’ll need to balance these multiple factors:

  • Schedule flexibility
  • Budget constraints
  • Weather considerations
  • School or work commitments
  • Property availability
  • Required moving services

While winter moves offer the best rates and most flexibility, they aren’t practical for everyone. When choosing your moving date, consider your specific situation and priorities. Remember, the best date ultimately depends on your unique circumstances and constraints.

Whether you’re planning months ahead or working with a tight deadline, strategic timing can make a significant difference in both your moving costs and stress levels. We’re here to help you with all your real estate needs. Give us a shout, and let us find ways to make your buying and selling experience less hectic!