Landscaping Services In Chicago

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.

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.

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.

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.

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.

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

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.

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.

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.

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.

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

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.