Plantings in Chicago

Garden beds, perennials, shrubs, and foundation plantings — designed for Chicago's seasons and installed by a family-owned crew that knows what survives here.

Plantings Built to Last More Than One Season

Most planting jobs in Chicago fail for the same two reasons: wrong plants for the spot, or right plants installed wrong. We handle the full process — walking the property, choosing plants based on your actual sun, soil, and drainage, prepping the beds (because nothing grows well in compacted clay), planting at the right depth and spacing, mulch top-coat to protect the roots, and a check-in visit to see how everything's settling. We work on everything from a quick spring refresh of one front bed to full multi-season install plans across an entire property. If you already have a landscape design drawn up — by us or by someone else — we'll execute it. If you don't, we'll walk the property with you and tell you straight what'll actually thrive in your specific conditions, and what won't.

TESTIMONIALS

What Our Plantings Customers Say About Us

Chicago Clay, Hard Winters, and Plants That Actually Survive

Here's why plantings in Chicago are harder than most people think. We're USDA Zone 6a — winter lows around -10°F, late frosts that can hit into mid-May, scorching humid summers, salt damage along every sidewalk and driveway, and clay soil that holds water in spring and bakes hard in August. Plants that thrive in Texas or California die here. We pick from species that actually survive: hostas, hydrangeas, viburnum, ninebark, oakleaf hydrangea, autumn joy sedum, coneflower, black-eyed susan, native asters, and perennials that come back fuller every year. For foundation plantings we lean toward boxwood, yew, and dwarf hydrangea — clean lines, slow growth, easy upkeep. For pollinator and native gardens we use Illinois natives that bring birds and butterflies without needing constant babysitting. When a planting job overlaps with landscape design, a mulch refresh, drainage work so plants don't drown, irrigation so they survive August, or hardscape edges so the beds stay where they belong — we handle all of that in-house too, instead of subcontracting it out.

Free On-Site Planting Consultations

Plant selection is something you can't do from a photo. Light, soil, drainage, salt exposure, the existing root systems underground, and what survives the alley wind tunnel between your building and your neighbor's — all of it matters. So we come out, walk the property, and give you a real plan based on your actual conditions. No pressure, no upsell. If you already know what you want, we'll source it and install it. If you want guidance, we'll tell you straight what'll thrive and what won't. Most planting projects land between $1,500 for a single bed refresh and $15,000+ for a full property install. We service most of Chicago's North Side, including Andersonville, Lincoln Park, Lakeview, Lincoln Square, Ravenswood, Roscoe Village, and surrounding neighborhoods.

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.