A new patio, a drainage fix or a full landscape renovation is a major investment, and the contractor you choose has as much impact on the result as the design itself. A great landscaper brings the project in on time, builds it to last and stands behind the work. A poor one can leave you with failed drainage, sinking pavers, dead plants and a partially finished yard.
The best way to tell the difference is to ask the right questions before you sign anything. This 2026 guide lists 15 questions to ask before hiring a landscaper, what good answers sound like, the red flags to watch for, and how to compare quotes fairly, with notes for homeowners in Naperville and the Chicago suburbs.
Before You Start Calling: Narrow the Field
Start with a short list of three or four companies:
- Ask neighbors whose yards you admire who did the work and how the experience went.
- Read recent reviews on Google and other platforms, paying attention to how the company responds to negative feedback.
- Look at portfolios for projects similar to yours: a drainage specialist and a lawn-mowing company are very different businesses.
- Check that they serve your town and are familiar with local soil, permitting and HOA rules.
Then schedule consultations and use the questions below.
Questions About the Company
1. What services do you specialize in?
“Landscaper” covers a wide range of businesses: lawn maintenance, planting design, hardscaping, drainage, irrigation, lighting and snow removal. Ask what share of their work looks like your project. A company that installs dozens of French drains every season will approach a drainage problem very differently from one that does it occasionally.
Good answer: specific examples of projects like yours and the crews or equipment dedicated to that work.
2. How long have you been in business, and who will actually do the work?
Experience matters, but so does who shows up. Ask whether the work is done by the company’s own crews or subcontracted, who the project lead or foreman will be, and how many projects they run at once.
3. Are you licensed and insured?
Illinois does not have a single statewide license for general landscaping, but specific work can require credentials. For example, commercial pesticide and fertilizer application is licensed through the Illinois Department of Agriculture, and irrigation systems involve state licensing for plumbing connections and backflow devices. Many municipalities also require contractor registration and permits for certain work.
Every company should carry general liability insurance, and companies with employees should carry workers’ compensation. Ask for a certificate of insurance. If an uninsured worker is injured on your property, you could be exposed to liability.
4. Can I see examples and talk to past clients?
Ask for photos of completed projects similar to yours, and if possible, references or addresses of work you can see from the street. Projects that are three to five years old are especially telling, because they show how the work holds up over time.
Questions About the Project
5. Can you show me a design or plan before work starts?
For anything beyond simple planting, you should see a plan: a drawing, layout or rendering that shows materials, dimensions, plant selections and drainage routes. A plan makes it much easier to compare quotes and prevents misunderstandings later.
6. How will you handle drainage?
This question separates experienced contractors from the rest. Patios, walls, new beds and grading all change how water moves around your home. A good contractor will explain where water will go, how the new work will be sloped, and whether downspouts, sump discharge or existing drainage need to be addressed. In the clay soils common across DuPage and Will counties, ignoring drainage is one of the most common reasons landscape projects fail.
7. What base preparation do you use for hardscapes?
For patios, walkways and retaining walls, the hidden base matters more than the visible surface. Ask about excavation depth, type and thickness of base stone, compaction methods, edge restraints and wall drainage. Vague answers here are a warning sign. See our guide to the best rock base for retaining walls for what good base work looks like.
8. Where do you source plants, and are they suited to our climate?
Plants should be appropriate for northern Illinois winters and your site conditions: sun, shade, wet or dry soil, and salt exposure near driveways. Ask about native options, mature sizes, and whether plants come from reputable nurseries.
9. Who handles permits, utility locates and HOA approvals?
Your contractor should call JULIE (811) before digging and know when permits are required for walls, drainage connections, grading or other work in your town. If you are in an HOA, ask whether they will help prepare submittals.
10. How long will the project take, and what could delay it?
Get an estimated start date and duration. Weather, material delays and inspections can affect schedules, but a contractor should be able to explain their sequence and how they communicate changes.
Questions About Cost and Contracts
11. What exactly is included in the price?
Ask for an itemized or clearly scoped quote that covers materials, quantities, labor, equipment, disposal, restoration of disturbed areas, permits and cleanup. Two quotes with different scopes cannot be compared fairly.
12. What is the payment schedule?
A reasonable deposit to schedule work and order materials is common, with progress payments tied to milestones and a final payment on completion. Be cautious of contractors who want most or all of the payment up front.
13. How are change orders handled?
Projects often evolve once work begins. Ask how changes are priced and approved. Changes should be agreed in writing before the extra work is done.
Questions About After the Job
14. What warranty do you offer?
Ask what is covered, for how long and what is excluded: workmanship on hardscapes, plant replacement, drainage performance. Get the warranty in writing. For example, Ware Landscaping backs qualifying drainage systems with a 10-year drainage guarantee.
15. What maintenance will my new landscape need, and can you provide it?
New plantings need watering, patios need joint sand and occasional cleaning, and drainage systems need outlets kept clear. Ask what you will be responsible for and whether the company offers maintenance or seasonal services.
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Extra Questions for Specific Projects
Hiring for drainage work
Drainage is technical work, and mistakes are expensive to undo. In addition to the questions above, ask:
- How will you determine where the water is coming from before designing the system?
- Where will the water discharge, and is that outlet allowed by the town?
- How deep and how wide will the trenches be, and what slope will the pipe have? (Our guide on how deep a French drain should be covers typical specs.)
- Will you use filter fabric, clean washed stone and cleanouts?
- How will you handle downspouts and sump pump discharge?
- What happens if water problems continue after installation?
Also see our article on who to call for yard drainage issues.
Hiring for patios and retaining walls
- What manufacturer and product line will you use, and does it carry a product warranty?
- How deep is the excavation, and how thick and compacted is the base?
- For walls: will there be drainage stone and a drain pipe behind the wall, and does the height require geogrid or engineering?
- How will the patio be sloped so water runs away from the house?
Hiring for snow removal
- At what snowfall depth will you plow, and how quickly after a storm?
- Is salting or pre-treating included or extra?
- Do you clear walkways and steps, or only driveways?
- How do you protect lawns, landscape edges and pavers?
- Is pricing per push, per event or seasonal? Our snow removal cost guide explains the options.
What a Good Consultation Looks Like
A professional consultation should feel like a conversation, not a sales pitch. Expect the contractor to walk the property with you, ask about how you use the space, look at drainage patterns and existing problems, take measurements and photos, and discuss budget openly. They should explain options with pros and cons rather than pushing a single solution, and follow up with a written proposal in a reasonable time. If a contractor quotes a price without looking closely at the site, or cannot explain what is included, keep looking.
Questions a Good Landscaper Will Ask You
The best contractors ask as many questions as they answer. If a company does not ask about these things, it may be guessing at what you need:
- How do you want to use the space: entertaining, kids and pets, gardening, quiet relaxation?
- What is your budget range, and are you open to phasing the project over several seasons?
- Where does water collect, and has the basement ever had moisture?
- How much time do you want to spend maintaining the landscape?
- Are there underground utilities, irrigation lines, invisible dog fences or existing lighting we should know about?
- Do you have HOA rules, easements or neighbor concerns?
- Are there future plans, such as a pool, addition or fence, that the design should allow for?
Answering these honestly helps the contractor design something that fits your lifestyle and budget, and avoids costly changes once work has started.
Landscaping Contractor Red Flags
- No written contract, or a contract with vague scope and no dates.
- No proof of insurance, or reluctance to provide it.
- Pressure to sign immediately or “today only” pricing.
- A price far below every other quote, often a sign of skipped base work, drainage or restoration.
- Large upfront payment demands or cash-only deals.
- No physical address, website or verifiable reviews.
- Dismissing drainage or base preparation questions.
- Poor communication during the quoting process, which rarely improves after you sign.
How to Compare Landscaping Quotes
| Compare | What to look for |
|---|---|
| Scope | Same project size, materials and features in each quote |
| Base and drainage | Depth, materials and compaction for hardscapes; drainage routes and outlets |
| Materials | Brand, style and grade of pavers, wall block, stone and plants |
| Restoration | Sod, seed, topsoil and cleanup after construction |
| Schedule | Start date, duration and sequence |
| Warranty | Coverage, length and exclusions |
| Payment terms | Deposit, milestones and final payment |
The lowest quote is not always the best value. If one price is far lower, find out what it leaves out.
When Is the Best Time to Hire a Landscaper?
In the Chicago area, the best time to plan spring and summer projects is late fall through winter, when contractors have more time for design meetings and you can secure a spot on the schedule. Drainage and grading work is often best done in late summer and fall, before winter freeze and spring storms. Snow removal contracts are usually arranged in early fall.
Frequently Asked Questions
How many quotes should I get for a landscaping project?
Three is a good number for most projects. It gives you a sense of fair pricing and different approaches without making the process overwhelming.
Do landscapers need a license in Illinois?
There is no single statewide license for general landscaping, but specific services like commercial pesticide application and irrigation work involve state licensing, and many towns require contractor registration or permits. Always confirm insurance.
Should I pay a landscaper up front?
A reasonable deposit is normal. Paying most or all of the cost before work begins is risky. Tie payments to completed milestones.
What should a landscaping contract include?
Scope of work, materials, quantities, price, payment schedule, timeline, permits, change order process, warranty and cleanup responsibilities.
How do I know if a landscaper does quality work?
Look at projects that are several years old, read reviews that mention long-term results, and ask detailed questions about base preparation, drainage and plant selection.
Hire With Confidence
The right questions reveal how a landscaping company plans, builds and stands behind its work. Look for clear answers about drainage and base preparation, written scopes and warranties, proof of insurance and a portfolio of similar projects that have held up over time.
Ware Landscaping has been designing and building landscapes, hardscapes and drainage solutions for homeowners across Naperville, Downers Grove, Hinsdale and the western suburbs. We are happy to answer every one of these questions. Contact us to schedule a consultation.
Following these nine essential elements for landscape design will create a solid foundation
