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Chicago Lawn Maintenance & Weekly Cleanup Services

Keep your Chicago lawn clean, healthy and professionally maintained with a complete lawn maintenance package from Ware Landscaping.

Our Chicago lawn maintenance services are designed for homeowners, commercial properties and qualifying homeowners’ associations that want more than basic grass cutting. We provide full-service weekly care that includes mowing, trimming, edging, flower-bed cleanup, organic fertilizer, spring cleanup and fall cleanup.

Please note: we do not offer mowing-only service. Our lawn maintenance program is built for customers who want their entire yard and landscape maintained consistently throughout the season.

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10,000+ Happy Customers served

Lawn maintenance

“I have been using Ware landscaping since the business began about 15 years. I have used them for all services lawn maintenance, entire landscape redesign, hard scape replacing an old wooden deck with a beautiful stone patio and fire pit and sump pump and rain drainage systems. Great work ethic and team work.”

Serge Boccassini thumnail
Serge Boccassini

“I have been using Ware landscaping since the business began about 15 years. I have used them for all services lawn maintenance, entire landscape redesign, hard scape replacing an old wooden deck with a beautiful stone patio and fire pit and sump pump and rain drainage systems. Great work ethic and team work.”

Serge Boccassini

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Watch this Ware WEEKLY Cleanup and Lawn Maintenance Package Makeover

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LAWN MAINTENANCE

Full-Service Lawn Maintenance in Chicago

Chicago lawns need consistent care because the local weather can change quickly from season to season.

Spring often brings wet soil, leftover winter debris and early weed growth. Summer can create fast turf growth, humidity, compacted soil and overgrown beds. Fall brings heavy leaf drop, plant cleanup and preparation for winter.

Our full-service lawn maintenance program helps keep your property looking clean and cared for from spring through fall.

Depending on your package, services may include:

  • Spring cleanup
  • Weekly mowing
  • Trimming and edging
  • Weekly flower-bed cleanup
  • Weed removal in beds
  • Bush and shrub trimming
  • Organic fertilizer applications
  • Spot weed spraying
  • Grub control
  • Fall cleanup
  • Leaf cleanup
  • Optional snow removal
  • Optional drainage maintenance for qualifying drainage customers

The goal is to maintain the entire outdoor space, not just the grass.

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Why Chicago Lawns Need Consistent Maintenance

Chicago properties can face several lawn and landscape challenges.

Small city lots may have limited lawn space, compacted soil, shaded areas and heavy foot traffic. Larger residential and commercial properties may require more detailed mowing, edging, bed maintenance and seasonal cleanup.

Common Chicago lawn issues include:

  • Weed growth
  • Thin or patchy grass
  • Compacted soil
  • Leaf buildup
  • Overgrown flower beds
  • Drainage problems
  • Soil erosion
  • Summer heat stress
  • Snow and winter damage

Without routine care, a lawn can quickly become uneven, overgrown or unhealthy. Regular maintenance helps preserve curb appeal and protects the investment you have made in your landscape.

Complete Lawn Care, Not Mowing Only

Chicago properties can face several lawn and landscape challenges.

Small city lots may have limited lawn space, compacted soil, shaded areas and heavy foot traffic. Larger residential and commercial properties may require more detailed mowing, edging, bed maintenance and seasonal cleanup.

Common Chicago lawn issues include:

  • Weed growth
  • Thin or patchy grass
  • Compacted soil
  • Leaf buildup
  • Overgrown flower beds
  • Drainage problems
  • Soil erosion
  • Summer heat stress
  • Snow and winter damage

Without routine care, a lawn can quickly become uneven, overgrown or unhealthy. Regular maintenance helps preserve curb appeal and protects the investment you have made in your landscape.

What to Expect, Season by Season

Spring (April–May)

Spring cleanup, mulch installation once soil has fully warmed, and the season’s first organic fertilizer application, all timed to your lawn’s actual condition rather than a fixed date.

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Summer (June–August)

Weekly mowing and cleanups continue on a growth-based schedule, with ongoing fertilizer applications and spot weed treatment. Chicago’s humid summer months mean weekly attention to flowerbeds and walkways matters just as much as mowing — overgrowth compounds quickly in warm, wet conditions.

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Fall (September–November)

Two rounds of fall cleanup to manage leaf drop from Chicago’s mature tree canopy, plus a final fertilizer application to strengthen root systems before winter dormancy sets in.

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Winter (December–March)

For Lawn & Snow Combo customers, unlimited snow removal coverage for any snowfall of 1/2 inch or more, so your lawn care and winter property care never fall out of sync.

Chicago Lawn Maintenance Pricing

1 YEAR

8 months: April – November
Spring clean up, weekly mowing, weekly clean ups, organic fertilizer and fall clean up.

$698

Per month

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3 YEAR LOYALTY

8 months: April – November
Spring clean up, weekly mowing, weekly clean ups, organic fertilizer and fall clean up.

$598

Starting at

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Lawn & Snow Combo

12 months: January – December
Spring clean up, weekly mowing, weekly clean ups, organic fertilizer, fall clean up and unlimited snow removal 1/2”+

$565

Starting at

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Estimate Disclaimer

The prices listed are initial estimates and subject to change depending on the size of the property.

One-Time Spring Clean Up with Mulch Installation

For property owners who want a single seasonal refresh rather than an ongoing maintenance plan, our one-time spring cleanup includes weeding, bush trimming, flower and garden bed cleanup and edging, and 8 yards of mulch installation — starting at $1,995, with final pricing based on your lawn’s unique size and needs.

This service isn’t available standalone outside of spring, but it’s included in every lawn maintenance package and can also be paired with additional mulch installation services for larger properties.

Starting at

$1,995

The Spring Clean Up includes:

  • Weeding 
  • Trimming of bushes
  • Clean up and edging of flower and garden beds
  • 8 yards of mulch installation

The one-time spring clean up is not available as a stand-alone service. However, all of our lawn maintenance packages include this service, and it’s also available as a combination with mulch installation services.

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Lawn Maintenance + Drainage: Why It Matters Together

(A special lawn maintenance upgrade for our drainage customers only)

Ware Drainage, Weekly Clean Up, and Lawn Maintenance Package

The Ware Weekly Cleanup and Lawn Maintenance Package is designed to keep your Chicago property maintained throughout the growing season.

Spring Cleanup

Spring cleanup prepares the property after winter and helps reset the lawn and landscape for the new season.

This service may include:

  • Cleaning out flower beds
  • Blowing out debris
  • Edging beds
  • Trimming plants
  • Shrub pruning
  • Perennial bed cleanup
  • Fresh first mowing
  • Preparing the property for weekly maintenance

Spring cleanup helps remove winter debris and gives the yard a cleaner, healthier start.

Weekly Mowing

Weekly mowing keeps the grass at a consistent height during the growing season.

Our mowing service may include:

  • Cutting the lawn
  • Using a grass catcher where appropriate
  • Trimming hard-to-reach areas
  • Weed-wacking lawn edges
  • Power edging sidewalks
  • Blowing off walkways and driveways

Consistent mowing helps prevent overgrowth and keeps the property looking neat from week to week.

Weekly Flower-Bed Cleanup

Flower-bed maintenance is one of the most important parts of a complete lawn maintenance program.

Each week, our team can help maintain the visible landscape areas by:

  • Weeding flower beds
  • Edging bed lines
  • Cleaning debris
  • Trimming bushes and plants as needed
  • Keeping the property looking polished

This service helps prevent beds from becoming messy, overgrown or neglected during the season.

Organic Fertilizer and Weed Control

Healthy grass needs more than regular mowing.

Our Chicago lawn maintenance package includes an organic fertilizer program designed to support stronger turf growth. The program may include multiple seasonal applications, grub control and spot treatment for weeds.

Organic fertilizer helps improve soil health, support root growth and encourage a thicker lawn that can better compete with weeds.

Fall Cleanup

Fall cleanup helps prepare your property before winter.

This may include:

  • Leaf removal
  • Blowing out flower beds
  • Re-edging beds
  • Trimming plants
  • Cleaning landscape areas
  • Preparing the lawn for winter dormancy

Wet leaves can smother grass and leave the lawn vulnerable to disease and thinning. Timely fall cleanup keeps the property cleaner and helps reduce spring maintenance issues.

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Drainage Maintenance
and Ware WEEKLY
Clean ups and
Lawn Maintenance
Package Includes:

Ware Drainage, Weekly Clean Up, and Lawn Maintenance Package Includes:

A Lifetime Drainage Guarantee Upgrade

Drainage Maintenance
  • Biannual system test
  • Biannual addition and change out of special filters
  • Biannual cleanup of collection basins

Ware Weekly Clean Ups and Lawn Maintenance

  • Spring Clean Ups
  • Weekly Mowing
  • Weekly Clean Ups
  • Organic Fertilizer Program
  • Fall Clean Ups

Drainage customers receive a $100 Monthly Discount off lawn maintenance packages

(Ongoing Drainage Maintenance is FREE for Ware drainage customers. Our drainage systems come with a lifetime guarantee for customers who use our maintenance services)

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One-Time Spring Cleanup With Mulch Installation

For property owners who need a seasonal refresh, Ware Landscaping offers a one-time spring cleanup when packaged with mulch installation.

This service may include:

  • Weeding
  • Trimming bushes
  • Cleaning flower and garden beds
  • Edging beds
  • Installing 8 yards of mulch

Starting at $1,995

Final pricing may vary depending on property size, bed size, mulch quantity and cleanup requirements.

Please note: the one-time spring cleanup is not available as a standalone service. It is available when combined with mulch installation and is also included in complete lawn maintenance packages.

Lawn Maintenance and Snow Removal Combo

Chicago winters can make property care difficult. Snow, ice and freezing conditions can affect safety, access and curb appeal.

The Lawn and Snow Combo gives customers year-round property care from one team.

This package includes the regular lawn maintenance program during the growing season and unlimited snow removal during winter for snowfall of 1/2 inch or more.

It is a practical option for customers who want one service provider for both lawn maintenance and winter property care.

Drainage Maintenance for Qualifying Customers

Lawn maintenance can also be combined with drainage maintenance for qualifying drainage customers.

This upgrade may include:

  • Biannual drainage system testing
  • Biannual filter changes
  • Biannual cleaning of collection basins
  • Spring cleanups
  • Weekly mowing
  • Weekly cleanups
  • Organic fertilizer program
  • Fall cleanups

Drainage customers may receive a $100 monthly discount off lawn maintenance packages.

Ongoing drainage maintenance may also support the lifetime drainage guarantee for qualifying drainage customers who continue the maintenance program.

Residential Lawn Maintenance in Chicago

Our residential lawn maintenance service is designed for homeowners who want a clean and consistently maintained outdoor space without managing the work themselves.

Residential services may include:

  • Front-yard maintenance
  • Backyard maintenance
  • Side-yard mowing
  • Flower-bed cleanup
  • Shrub trimming
  • Edging
  • Organic fertilization
  • Leaf cleanup
  • Seasonal maintenance

This is a good option for homeowners who want the lawn, beds and outdoor areas maintained together instead of hiring separate services for mowing, cleanup and fertilization.

Commercial Lawn Maintenance in Chicago

Commercial properties need consistent maintenance because the exterior creates an immediate impression for customers, tenants, visitors and employees.

Ware Landscaping provides full-service lawn maintenance for qualifying Chicago commercial properties, managed properties and homeowners’ associations.

Commercial lawn maintenance may be suitable for:

  • Office properties
  • Retail properties
  • Multifamily properties
  • Homeowners’ associations
  • Managed residential properties
  • Commercial landscapes
  • Institutional properties

A clean and well-maintained exterior can improve curb appeal and help the property look professional throughout the season.

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Seasonal Lawn Maintenance in Chicago

Spring

Spring maintenance may include cleanup, bed edging, plant trimming, debris removal, mulch installation and the first fertilizer application of the season.

Summer

Summer maintenance may include weekly mowing, trimming, edging, flower-bed cleanup, weed control and ongoing organic fertilizer applications.

Fall

Fall maintenance may include leaf removal, plant trimming, bed cleanup, re-edging and preparation for winter.

Winter

Customers on the Lawn and Snow Combo can receive snow removal service during the winter season.

Why Choose Ware Landscaping for Chicago Lawn Maintenance?

Complete Weekly Care

Our packages include mowing, edging, trimming, flower-bed cleanup and seasonal services.

No Mowing-Only Shortcuts

We focus on complete lawn and landscape maintenance rather than simple mow-and-go service.

Organic Fertilizer Program

Our program supports healthier grass through seasonal organic fertilizer applications.

Spring and Fall Cleanup Included

Seasonal cleanup is built into the full-service lawn maintenance package.

Residential and Commercial Service

We maintain qualifying residential, commercial and HOA properties in Chicago.

Year-Round Options

Customers can combine lawn maintenance with snow removal for year-round property care.

Frequently Asked Questions

Mid-to-late spring, after the ground thaws and soil has a chance to warm up. Mulch supports soil health and plant growth by letting seedlings take root and thrive, but overmulching can kill grass and block nutrients from reaching plant roots — getting the depth and timing right matters as much as doing it at all.

Organic fertilizer promotes healthy, dense grass and plant growth, which creates shaded soil that blocks weed seeds from germinating. It also improves soil structure, strengthens grass root systems, and builds a physical barrier against weeds — a more sustainable approach than relying on herbicides alone.

An ineffective drainage system can cause significant damage, lower property value, and create health risks from mold and standing water. A properly designed drainage system, by contrast, prevents soil erosion, flooding, insect infestation, and swampy yard conditions before they start.

No. We provide complete lawn maintenance packages that include mowing as part of a broader program — we do not offer standalone mowing-only service. This lets us catch and address problems like compaction, early weed growth, or drainage issues during routine visits, rather than only showing up to cut grass.

Ware Landscaping’s Chicago lawn maintenance plans start at $565/month for a 12-month lawn-and-snow combo, with seasonal-only (April–November) plans starting at $598–$698/month depending on contract length. Final pricing depends on property size — request a free quote for an exact rate.

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Call Ware Landscaping Today

Chicago neighbors to keep their yards looking beautiful. been dedicated to helping you to create the yard of your dreams. 

We’re committed to providing the best in drainage, hardscape installation, landscaping lawn maintenance services, and snow removal services for our Chicago neighbors. Connect with Ware Landscaping today and let us transform and manage your lawn care to help create the amazing yard of your dreams.

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What people are saying

Ware Landscaping & Snow Removal

They did a great job and we are very pleased!

“I contacted Mike at Ware Landscaping for help with fixing my flooded backyard and garage. Mike gave me an honest assessment of my situation and recommended the right system to fix my problems (a lot of issues). Ware Landscaping installed drainage, underground downspouts, underground sump pump lines, driveway drains and surface drains in the yard to fix all my problems.. The team was very professional and always asked for my approval on work being done before it was completed. They did a great job and we are very pleased!”

Jim Kristof
stars

I recommend him without any hesitation.

“We had a water problem in our basement that Mike Ware completely eliminated by removing both our sump pump water and downspout water away from the home. He was professional and highly motivated to solve the problem and do it the right way. I always felt like a priority and that my project mattered. I recommend him without any hesitation.”

Michael Swider
stars

FANTASTIC JOB!!!

Ware Landscaping did a FANTASTIC JOB!!! I needed my entire backyard regraded and they filled it in with more than 2 truck loads, installed a French drain and put new beautiful green sod on top. They also power washed and reset my front retaining wall. Communication from the beginning was always very good. We always knew when they were coming out. The project was completed on time as well. They also called on their own a month after the project to check on the sod and were willing to replace some spots due to the June heat wave. Would recommend Ware Landscaping to all!!!”

Dan Malloy
stars

The entire crew were incredible, so friendly, knowledgeable, and paid attention to every detail.

“Mike, Greg and the rest of the crew made our back yard dream a reality with a drainage system to remove the stream that flowed through the middle of the yard, which flooded every rainstorm and stuck around for weeks. To complete the look in came a perfectly designed beautiful hardscape patio that we can’t wait to use this summer. The entire crew were incredible, so friendly, knowledgeable, and paid attention to every detail. Highly recommend!”

Katie Jankowski
stars

The crew was fast, friendly, and tidy.

“We had a wooden deck for a front porch that was starting to age. When we removed it we saw that there was a concrete slab underneath it that was pitched toward our house, creating an issue with standing water up against our foundation. We had Mike come by to advise us on the best solution, and he suggested permeable pavers. We were able to come up with a custom design with him that day. The crew was fast, friendly, and tidy. I’m sure they do much bigger jobs than our little patio, but this project made a huge difference for our home.

Cecily Ivey
stars