When the North Shore turns quiet and lawns disappear under snow, it can feel like landscaping is on pause. In reality, winter is one of the best times to plan a Chicago landscape design, especially if you want a clean, efficient build as soon as spring weather arrives.
Homeowners and HOAs in Libertyville, Lake Forest, and across the North Shore often wait until April to start calling a landscape designer. By then, design calendars fill quickly, material lead times stack up, and permitting or HOA approvals can delay the first shovel in the ground. Planning during the off-season helps you avoid that scramble and positions your project for a smoother start when crews can finally work consistently.
Below is a practical look at why winter planning pays off, and a simple timeline you can follow to move from ideas to a spring installation without stress.
Why Winter Is the Best Season to Start Landscape Planning
A landscape design and installation project has more moving parts than most people expect. Design decisions affect grading, drainage, hardscape layout, lighting, planting, and how the space will function through every season. Winter is ideal for mapping those decisions because you have time, attention, and flexibility.
Here is what winter planning gives you that spring planning rarely does.
1) Clearer budgeting and smarter phasing
Winter is a great time to define what you want and what you want to spend, before the pressure of “we need this done now” takes over. With a thoughtful plan, you can:
- Prioritize must-haves vs nice-to-haves
- Build a realistic budget for each phase
- Decide where premium materials matter most
- Avoid costly change orders mid-installation
2) Better access to design schedules
Landscape designers and landscape design and installation teams tend to book up quickly in the spring, especially in the Chicago suburbs. Reaching out in winter increases the odds you can:
- Schedule your site survey at a convenient time
- Get multiple concept options without rushing decisions
- Reserve an installation window early
- Keep your spring and early summer calendar open
In short, winter planning is how you get ahead of the seasonal rush.
3) Material lead times are real, and they can affect your start date
Many projects are delayed not by labor but by materials. Natural stone, specialty pavers, custom fabricated features, lighting packages, and even certain plant sizes can have lead times that stretch into weeks.
When you plan in winter, you can order and stage materials before spring demand spikes. That helps protect your install timeline, especially if your project includes:
- Patios, walkways, or retaining walls
- Outdoor kitchens or fire features
- Drainage systems and grading work
- Landscape lighting
- Large-caliper trees or coordinated plant palettes
4) Permitting and HOA approvals take longer than people expect
Depending on your scope, you may need approvals for grading, drainage, fencing, structures, or changes near easements. Even when permits are not required, if you need HOA approval, that can add weeks.
Winter gives you room to handle these steps without delaying construction. It also allows time to revise drawings based on feedback without compromising the final plan.
5) Winter exposes the “bones” of the property
Without foliage, it is easier to see:
- Drainage patterns and low spots
- Sightlines, privacy gaps, and exposed areas
- Hardscape edges, settling, or heaving
- The true structure of trees and shrubs
- Places where a landscape feels empty or disconnected from the home
A good site survey and design process uses that clarity to create a landscape that looks intentional in every season, not only when everything is green.
The Core Pieces of a Strong Winter Planning Process
If you want spring installation to feel smooth, winter is the time to lock in the fundamentals.
Step 1: Define how you want to use the space
Before choosing materials or plants, get specific about function. Ask yourself:
- Do you want a space for entertaining, relaxing, or both?
- Is this primarily a front-yard curb appeal upgrade, or a backyard living space?
- Do you need better drainage or grading fixes?
- Is privacy a goal, especially in winter when trees are bare?
- How much maintenance do you want long-term?
This is where working with a landscape designer helps, because they translate lifestyle goals into a layout that actually works on your property.
Step 2: Get a site survey and measurements early
A site survey is the foundation of a reliable landscape design. It captures grading, elevations, existing structures, utility considerations, and the footprint you are working with. Winter planning means you can schedule this early and build your design around accurate information, not guesses.
Even if final work waits for warmer weather, your design decisions become faster and more confident once you have real measurements.
Step 3: Align the design with the budget and build strategy
Great designs are not only beautiful, they are buildable. During winter planning, you can review options and choose the right approach:
- One comprehensive build in spring
- A phased plan across spring and summer
- A multi-year strategy (common for larger properties)
This is where “landscape design and installation” planning matters. A design that ignores construction reality often becomes expensive later. A design created with installation in mind tends to stay on schedule and within budget.
Step 4: Decide on materials and place orders before spring demand peaks
Once the design direction is set, winter is the time to select and confirm:
- Paver or stone type, color, and pattern
- Wall and coping materials
- Steps, edging, and border details
- Lighting fixtures and transformer needs
- Drainage solutions and grading scope
- Key plant sizes and evergreen structure
Early decisions help avoid last-minute substitutions that change the look and feel of the project.
Step 5: Start permitting and approvals early, even if you are not breaking ground yet
If your project touches drainage, structures, fences, or anything that may require a permit or HOA review, get that process moving during winter. It is much easier to adjust plans on paper than to stop a project once work begins.
Common Winter Planning Questions
“Can you really design a landscape when everything is frozen?”
Yes. A professional site survey captures the property’s structure, grades, and existing elements regardless of season. Winter can actually make certain issues easier to identify, especially drainage paths, exposed views, and the true shape of trees and beds.
“What if we are not sure about the full budget yet?”
That is exactly why winter planning helps. You can develop a design that supports phased implementation, so you get a cohesive long-term plan even if you build it in steps.
“Will early planning actually get us installed earlier?”
Often, yes. Design schedules and installation calendars fill fast in spring. Planning early helps you secure a better spot and prevents delays caused by late approvals or material lead times.
Planning Now Means Enjoying More of Spring Later
A thoughtful Chicago landscape design starts long before plants go in the ground. Winter is your opportunity to make decisions with clarity, avoid spring bottlenecks, and set your project up for a smooth start when the weather turns.
If you are considering a landscape design and installation project in Libertyville, Lake Forest, or anywhere along the North Shore, winter is the right time to begin. The goal is simple: when spring arrives, you are not scrambling, you are building.
Contact Martin John Company today to schedule a consultation and start planning a landscape that is ready to come to life as soon as the season changes.