Tree Removal in Chicago

Safe removal of dead, diseased, hazardous, and storm-damaged trees — from full takedowns to single limbs — with stump grinding and full debris haul-off included.

Tree Removal That Doesn't Take Out Your Garage

The hard part of tree removal in Chicago isn't cutting the tree down — it's getting it down without dropping it on your roof, your neighbor's fence, the parkway, or the alley power lines. We work tight city lots every day. Trees come down in sections, climbed and rigged from above, with controlled drops onto tarps to protect the lawn underneath. We handle full removals (everything from sapling to mature 80-foot oaks), selective limb pruning for safety or sight lines, dead and diseased tree removal where the structural integrity is already gone, and emergency storm work when a limb's split or a tree's leaning over the house. Stump grinding is a separate add-on most jobs include — standard grind goes 4 to 6 inches below grade, deep enough to lay sod or plant over without issue. Debris hauls off the same day. Your yard looks like we were never there.

Parkway Trees, Permits, and the Chicago Bureau of Forestry

Here's where most homeowners get stuck. The trees between your sidewalk and the street — the parkway trees — aren't yours. They belong to the city, and any work on them has to go through the Chicago Bureau of Forestry. You can't legally just call someone to take one down. We've handled the permit process enough times to walk you through it: dead-tree removal requests, hazard determinations, inspections, the timeline (it's not fast), and what happens after if the city plants a replacement. For trees on your private property — backyard, front yard within the property line, between buildings — no permit needed and we can usually be out within a few days for non-emergencies, sooner if it's a hazard. We also handle the rest of the seasonal calendar: spring deadwood pruning, summer canopy thinning to let light through, and fall preventative work before winter storms hit. If the work creates other follow-on jobs (sod where the canopy is now gone, hardscape repair where roots cracked the patio), we handle those in-house too.

Free On-Site Estimates and Emergency Calls

Tree work is one of the few things you really can't price over the phone — height, condition, access, and what's underneath all matter. We'll come out, walk it, give you a real number, and tell you straight whether the tree actually needs to come down or whether some pruning solves the problem. Free, no pressure. For emergencies — a leaning tree after a storm, a split limb hanging over the driveway, anything dangerous — call us at (773) 305-6559 and we'll triage same-day. We service most of Chicago's North Side, including Andersonville, Lincoln Park, Lakeview, Lincoln Square, Albany Park, Rogers Park, and the surrounding neighborhoods.

TESTIMONIALS

What Our Tree Removal Customers Say About Us

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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.