Landscaping in Chicago

Complete landscape installation and planting services to transform your Chicago outdoor space — beds, borders, trees, shrubs, and perennials chosen for the climate and built to last.

Landscape Installation That Actually Establishes

A new landscape isn't just plants in dirt — it's plants chosen for the right spot, in soil that's been amended to actually support them, planted at the right depth, and watered through the establishment window where most installs fail. We start every job with proper bed prep: tilling compacted clay, amending with compost or quality topsoil so roots can move, and shaping beds so water drains away from the house instead of pooling against it. Plants get installed at the right depth (the most common mistake on cheap landscaping jobs is planting too deep — the crown smothers and the plant declines for two years before dying), spaced based on mature size rather than what looks full on day one, and mulched with hardwood at proper depth. We handle full yard installs, foundation plantings, perennial borders, shrub massings, privacy hedges, ornamental and shade tree planting, native and pollinator gardens, and seasonal color rotations (spring tulips and pansies, summer annuals, fall mums and ornamental cabbage). Every job comes with a written care plan — what to water, when to prune, when to expect bloom — so you actually know what you bought.

Plants That Actually Survive a Chicago Winter

Chicago is USDA Zone 5b/6a, which is harsher than most homeowners realize. Plants that look great at a suburban garden center can be borderline-hardy here, and a hard winter takes them out. We pick from a list of plants we've actually watched survive multiple Chicago winters: hydrangeas (paniculata and arborescens, not the macrophylla varieties that struggle in cold), boxwood for hedging, daylilies and hostas for the workhorses of any perennial bed, ornamental grasses like Karl Foerster and Northwind, native species like coneflower, black-eyed susan, and little bluestem for low-maintenance pollinator beds, and shade trees that handle clay and urban conditions — serviceberry, redbud, Kentucky coffeetree, and the right oaks. We avoid plants we've watched die in Chicago no matter how often the local nurseries push them. For full backyard rebuilds we usually start with a landscape design — a scaled plan with planting specs and material callouts — but for foundation refreshes, bed updates, or single-area installs we can plan and plant in the same visit. Pair with irrigation for newly installed beds (the difference between a thriving install and a struggling one), mulching for protection and curb appeal, and ongoing lawn maintenance to keep the surrounding turf in shape.

Free On-Site Estimates for Landscape Installation

We can give rough ballparks over the phone for simple jobs — refreshing a foundation bed, replacing a row of dead boxwood — but most landscaping projects we'll come walk in person. Plant selection, bed shape, sun exposure, soil condition, and how the space will actually be used all affect what makes sense. The site walk is free, no pressure, and you'll get a real number with itemized plant counts and prep work — not a placeholder you'll "be approved for." We service most of Chicago's North Side, including Andersonville, Lincoln Park, Lakeview, Lincoln Square, Logan Square, Albany Park, and the surrounding neighborhoods. Spring planting slots fill up by mid-March, and fall planting (often the better window for trees and shrubs) fills up in August. Call us at (773) 305-6559 or request a quote online.

TESTIMONIALS

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FREQUENTLY ASKED QUESTIONS

Are you licensed and insured?

Yes — fully licensed and insured for residential and commercial landscaping work in Chicago. We're happy to send proof of insurance before any job. Honestly, you should be asking every contractor for the same.

What Chicago neighborhoods do you serve?

We service most of Chicago's North Side, including Albany Park, Andersonville, Irving Park, Lakeview, Lincoln Park, Lincoln Square, Logan Square, North Center, Ravenswood, Rogers Park, Roscoe Village, Uptown, and West Ridge. If you're nearby and not on the list, give us a call — chances are we can still help.

Are you really a family business?

Yes. O'Brien Brothers Landscape was started by Emmet O'Brien, a Chicago kid who started cutting lawns at twelve and never really stopped. We've grown a crew and added trucks, but the company is still local, still owner-run, and the name on the truck is the name answering the phone.

How do I get a quote?

Call us at (773) 305-6559 or message through our site. For routine work we can ballpark over the phone; for design, hardscape, or larger installs we'll come walk the property in person — free, no pressure.

How often should my lawn be mowed in Chicago?

During peak growing season (May through August), most Chicago lawns need cutting every 7 days. In spring and fall, every 10–14 days is usually enough. We offer weekly, bi-weekly, and one-time service depending on what your lawn actually needs.

Do you do residential snow removal?

Yes — driveways, walkways, front steps, and back paths. We service homes and commercial properties across the North Side.

When should I mulch my beds in Chicago?

Late April through mid-May is the ideal window — soil has warmed up, weeds haven't established yet, and your beds look sharp heading into summer. A lighter fall refresh in October helps insulate roots through winter.

When is the best time to install sod in Chicago?

Best windows are mid-April through June, and late August through October. Peak summer heat is rough on establishing roots, so we avoid it when we can. Technically sod can be laid any time the ground isn't frozen, but timing strongly affects how well it takes.

Do you install full sprinkler systems?

Yes — full design and installation including heads, zones, valves, controller, and backflow. We use commercial-grade components, not big-box parts that fail in three seasons.

What does a landscape design include?

A scaled site plan, a planting plan with species suited to Chicago's climate (and your specific sun/soil conditions), and material specs for any hardscape elements. For larger projects we can include 3D rendering so you see exactly what you're getting before we break ground.

Do you build patios, walkways, and retaining walls?

Yes — paver patios, natural stone, poured concrete, brick walkways, retaining walls, fire pits, outdoor kitchens. Styles range from clean modern to traditional Chicago bungalow.

What's the difference between concrete and pavers?

Concrete is cheaper upfront but cracks in Chicago freeze-thaw cycles and is hard to repair cleanly. Pavers cost more but flex with the ground, last decades, and any individual stone can be lifted and reset if it ever shifts. For most North Side homes, pavers are the long-term value play.