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Outdoor ServicesUpdated 2026

Landscaper in Chicago, IL

Research local landscapers in Chicago, Illinois. Compare LocalPros directory profiles, pricing guidance, and hiring tools before you contact businesses directly.

3 Profiles

In your area

4.5 Avg Rating

666 total reviews

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See how much landscaper costs in Chicago

Average rates, common job prices, and money-saving tips

Landscaper Research Profiles in Chicago

3 profiles found

The profiles below are part of the LocalPros research directory, not a live contractor marketplace. Use them as comparison starting points, then submit your project request if you want LocalPros to generate a recommendation shortlist for your specific service and location.

Windy City Landscaping

4.5(250 reviews)
12+ years

If the job involves retaining walls or seasonal cleanup, Windy City Landscaping fits the kind of profile homeowners usually shortlist. The card shows 12 years in business and 250 reviews.

Best fit for

license-conscious homeowners
12 years in business
Free Design ConsultationSeasonal PackagesIrrigation Experts

Lakeside Lawn & Garden

4.5(222 reviews)
19+ years

The profile for Lakeside Lawn & Garden leans toward yard redesigns and drainage work rather than broad general contracting. It carries a 4.5-star average across 222 reviews.

Best fit for

license-conscious homeowners
19 years in business
Certified Landscape DesignerPaver PatiosOutdoor Kitchens

Midwest Landscape Design

4.5(194 reviews)
27+ years

Midwest Landscape Design reads more like a fit for irrigation installs and planting plans and similar household project work. There are 194 reviews on record, which gives homeowners something tangible to compare.

Best fit for

license-conscious homeowners
27 years in business
Lawn Care ProgramsHardscapingFree Consultations

Local Insights: Landscaper in Chicago

Licensing Authority

City of Chicago Department of Buildings — contractors need a City business license plus trade-specific licenses for electrical and plumbing

Verify a license →

Climate & Your Home

Extreme cold winters (temps can drop below -20°F) and hot humid summers put heavy strain on HVAC systems and increase pipe freeze risk.

Permit Requirements

Chicago DOB permits required for structural, electrical, plumbing, and HVAC. Some neighborhoods require aldermanic sign-off for exterior changes.

Seasonal Tip

Insulate pipes before November. Schedule furnace inspection in August — Chicago HVAC contractors book up fast once temperatures drop in October.

Chicago-Specific Questions

What licenses do Chicago contractors need?

Chicago contractors need a City of Chicago business license. Electricians need a City electrical license; plumbers need a City plumbing license. Always verify the license is active at chicago.gov.

Are basement flooding issues common in Chicago?

Yes. Chicago's combined sewer system causes basement backups during heavy rain. Ask any plumber about overhead sewer conversion or backwater valve installation, which can dramatically reduce flood risk.

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Frequently Asked Questions About Landscapers in Chicago

What should I ask before hiring a landscaper in Chicago?

Ask whether drainage, haul-away, and maintenance expectations are in scope instead of assuming they are bundled into the design price. Also ask for a written scope, pricing breakdown, and the credentials or insurance documentation that apply to this trade before work starts.

What usually affects landscaper pricing in Chicago?

In Chicago, quotes usually move with lot size, grading needs, irrigation complexity, plant material, and hardscape scope. Extreme cold winters (temps can drop below -20°F) and hot humid summers put heavy strain on HVAC systems and increase pipe freeze risk.

Do permits or inspections matter for landscaper work in Chicago?

Chicago DOB permits required for structural, electrical, plumbing, and HVAC. Some neighborhoods require aldermanic sign-off for exterior changes.

How much does professional landscaping cost?

Basic lawn maintenance runs $100-$300 per month, while landscape design and installation projects range from $3,000 to $30,000+ depending on scope. Common costs include sod installation ($1-$2 per sq ft), paver patios ($15-$25 per sq ft), retaining walls ($20-$45 per sq ft), and irrigation systems ($2,500-$5,000).

What should I look for in a landscaper?

Look for proper licensing and insurance, a portfolio of completed projects, references from recent clients, clear written contracts with detailed scope of work, and knowledge of local plant species and climate considerations. For larger projects, choose a company with landscape design credentials (landscape architect or certified designer).

When is the best time to start a landscaping project?

Spring and fall are ideal for most landscaping projects. Plant in spring after the last frost for best establishment, or in early fall when temperatures cool but roots still grow. Hardscaping (patios, walls, walkways) can be done year-round in mild climates. Book contractors 4-8 weeks in advance during peak season.

About Landscaper Services in Chicago, Illinois

Landscaper projects in Chicago usually involve drainage corrections, irrigation work, planting plans, retaining walls, and seasonal cleanup. Extreme cold winters (temps can drop below -20°F) and hot humid summers put heavy strain on HVAC systems and increase pipe freeze risk.

Local quotes usually move with lot size, grading needs, irrigation complexity, plant material, and hardscape scope. Chicago DOB permits required for structural, electrical, plumbing, and HVAC. Some neighborhoods require aldermanic sign-off for exterior changes.

Hiring note: Ask whether drainage, haul-away, and maintenance expectations are in scope instead of assuming they are bundled into the design price.

DIY vs. hire a pro: Mulching and planting are approachable DIY tasks. Drainage correction, irrigation, and retaining walls usually need a pro.

Landscaper in Chicago, IL (2026) | LocalPros | LocalPros