How to Find a Reliable Tree Removal and Trimming Service Near You in Chicagoland

September 21, 2026

Finding the right tree removal and trimming service near you comes down to three checks: confirm the company carries insurance for tree work, ask how they time the job around the species involved, and find out what they leave behind once the tree is gone. That last part is where we come in. Tommy Pollina Landscape Company handles the regrading, drainage tie-ins, and replanting that follow a big tree coming down, across the North Shore and Northwest suburbs.

Key Takeaways

• A licensed, insured tree contractor should assess the property in person before quoting, not just over the phone.
• Oaks shouldn't be pruned from March through October, since that stretch is when oak wilt spreads fastest.
• A tree's root system can be quietly working against your grading and drainage for years before anyone notices.
• Tommy Pollina Landscape Company has completed more than 10,000 drainage installations across Chicagoland, work that often follows a tree coming out of the ground.

What Should I Look for in a Tree Removal Company Near Me?

Look for a company that's licensed and insured for tree work, sends someone to walk the property before quoting, and puts removal, cleanup, and stump handling in writing. Ask how the crew protects fences, sprinkler lines, and hardscape near the work zone. Falling limbs and heavy equipment can do damage fast.

That last point matters more than people expect. Bucket trucks and stump grinders are heavy, and they don't always take the shortest path to the tree. If a crew's equipment tracks across a paver patio or clips a retaining wall on the way in, get it noted and photographed before the truck leaves. Damage to brick and stone hardscape is easy to fix when it's caught right away, and a lot harder to repair once it's been driven over a few more times during the job.

A written scope should also spell out where the debris goes. Some companies chip and haul everything the same day; others leave logs and brush for the homeowner to deal with. Ask before you sign anything, not after.

When Is the Best Time to Trim or Remove a Tree in Chicagoland?

Most deciduous trees handle trimming best during the dormant season, from late fall through early spring. Oaks are the exception: they shouldn't be pruned from March through October, since that window is when oak wilt spreads fastest. Removing a dead or hazardous tree doesn't wait for a season. A fall risk to a roof or driveway needs attention right away.

That distinction trips up a lot of homeowners. Trimming has a calendar built around plant health and disease risk. Removal has a different one, built around safety. A cracked trunk leaning toward a roofline in July doesn't get to wait until November just because that's when pruning is usually scheduled. If you're not sure which category your situation falls into, an in-person look from a tree professional will settle it faster than guessing.

What Happens to My Yard After a Tree Comes Down?

Removing a mature tree leaves a bare patch of disturbed soil, a stump or grindings, and often a root system that's been interfering with grading or drainage for years without anyone noticing. The ground around the old trunk can settle unevenly over the following season. Regrading, drainage tie-ins, and new plantings are what turn that gap back into usable yard.

Root Systems and the Drainage Problems They Leave Behind

A tree's roots don't just anchor it. Over ten or twenty years, they can shift soil, block a downspout run, or push a low spot into the yard that only shows up as standing water after the tree is gone. We hold NDS Professional Drainage Contractor Certificates, and our drainage systems work uses laser-guided measurements and exact elevations to move water below grade, away from the house, into french drains, channel drains, or river rock systems depending on what the property needs. When a removal uncovers a root mass that's been sitting under a wet spot for years, that's exactly the kind of thing a proper regrade and drainage plan is built to solve.

Filling the Gap With New Plantings and Grading

Once a tree is out, the space it leaves behind is an opportunity, not just a problem to patch. Our landscape design work maps grading, drainage, and planting together in one plan, with 3D renderings so you can see a replacement tree or a new privacy screen before anything goes in the ground. We've installed everything from Green Giants and Blue Arrow Junipers for screening to Japanese Maples and flowering shrubs like hydrangeas and Spirea as focal points, depending on what the spot calls for. A single removal often opens up sun exposure the rest of the yard didn't have before, which changes what will actually thrive there.

For Commercial Properties and HOAs

Commercial sites and HOAs deal with larger, older trees more often than single-family homeowners do, usually near parking areas, entrances, or shared green space. Once the tree work is finished, the regrading and drainage tie-in on a commercial property has to hold up to the same foot traffic and municipal drainage standards as the rest of the site. Our commercial landscaping work across the North Shore covers exactly that follow-up piece, alongside the broader landscaping and hardscaping services we run on properties of every size.

What to Check Before You Hire a Tree Crew

Frequently Asked Questions

How do I know if a tree needs to come down instead of just being trimmed?

Signs that point toward removal instead of trimming include a trunk leaning noticeably more than it used to, large sections of dead canopy, fungal growth or soft wood near the base, and roots that have visibly heaved or split near the trunk. Any of these warrants an in-person look from a tree professional rather than a guess from the ground.

Does removing a large tree change my yard's grading or drainage?

Yes, often. A mature tree's root system can hold soil in a shape that's been masking a low spot or a blocked flow path for years. Once the roots are gone and the ground settles, water that used to disappear can start pooling. That's the kind of grading and drainage work we handle once tree work is finished.

What happens to the stump after a tree comes down?

A stump can either be ground down below grade so soil and sod cover it, or removed entirely along with the root ball, which leaves a larger hole to fill. Grinding is faster and cheaper; full removal is necessary if you're planning to install hardscape, a foundation, or anything else that needs solid, root-free ground underneath.

When should tree work be scheduled before winter?

Getting tree work done before the ground freezes gives the yard time to recover before spring. If a removal leaves bare soil or debris right before winter, our Fall Cleanup program addresses debris removal and lawn prep starting in late October and running through December, so the yard isn't sitting exposed all season.

If a tree removal on your property left bare soil, an uneven grade, or a low spot that didn't used to hold water, tell us about it using the form below. We'll walk through what it takes to regrade, drain, and replant that space properly.