O'Brien Brothers Landscaping started in 2005 with Emmet O'Brien, a Chicago kid cutting lawns at twelve who built it into a full design-build crew. Today we work across the North Side handling landscape design, hardscape, plantings, drainage, irrigation, and outdoor lighting. Owner-run, same crew start to finish, every job finished cleaner than we found it. See what we've built across Lincoln Park, Lakeview, Andersonville, and the rest of the North Side on our gallery, or follow @obrienbrotherslandscaping on Instagram and TikTok where we show our work.


Custom 2D plans drawn to scale — every patio, planting bed, walkway, and lighting fixture mapped before we break ground. We design around Chicago's climate, soil, and sun patterns. Build it all at once or stage it over seasons.

Paver patios that survive Chicago freeze-thaw. Every install gets 6–8 inches of compacted base, polymeric sand joints, and edge restraints. Unilock, Techo-Bloc, Belgard. We also handle retaining walls, fire pits, outdoor kitchens, and walkways.

Zone 6a hardy shrubs, perennials, native species, and ornamental trees sized for Chicago lots. Every plan accounts for mature size, sun exposure, and seasonal interest so the yard looks intentional 12 months a year.

Standing water is a foundation problem waiting to happen. We diagnose the root cause — grading, downspouts, clay, buried debris — and install French drains, catch basins, dry wells, or subsurface systems.

Smart sprinkler systems with Wi-Fi controllers (Hunter, Rain Bird, Rachio) zoned by sun exposure and plant type. Drip for beds, rain sensors, freeze protection on every system. Spring startups and winterizations included.

Low-voltage LED path, accent, security, and smart fixtures with app control. Transformers sized for future expansion so you can add zones later without rewiring.

Fresh-cut Kentucky Bluegrass from Illinois growers. Best installed mid-April to early June or September to mid-October. Includes soil prep, grading correction, and a follow-up watering schedule.

Hardwood, cedar, dyed, and pine bark each spring (and fall for winter protection). Includes edge cleaning, bed redefinition, and weed pulling so it looks like a fresh design, not just a fresh layer.

Per-event and seasonal contracts for North Side properties. Driveways, walks, entryways. Salt included, fully insured. Priority routing for maintenance clients.

Call us or fill out the form. We come out, walk your property with you, listen to what you actually want, and take measurements. No charge, no pressure.

We design the project, source the materials, and give you a flat-rate quote with no surprises. For larger jobs you get 3D renderings so you see exactly what you're getting before we break ground.

One crew, start to finish, from first dig to final cleanup. Same names, same trucks, every day. We leave your yard cleaner than we found it.
We've been working these neighborhoods since 2005 — from Edgewater down to Lincoln Park and west to Logan Square. Same crew, same standards, regardless of zip code. Tap your neighborhood to see local work.
Landscaping costs in Chicago typically range from $5,000 to $75,000+ depending on scope. A spring cleanup with fresh mulch and seasonal plantings runs $2,500–$5,000. A full backyard renovation with patio, plantings, and lighting averages $25,000–$50,000. Complete design-build outdoor living spaces with hardscape, outdoor kitchen, irrigation, and lighting can range from $60,000 to $150,000+. Every O'Brien Brothers quote is flat-rate after an in-person walkthrough — you'll know the total before we break ground, and there are no change orders mid-project.
A paver patio in Chicago typically costs $25–$40 per square foot installed, depending on materials and site conditions. A 300 sq ft patio runs $7,500–$12,000 with mid-grade pavers, proper base prep, and edge restraints. Premium materials like Unilock Beacon Hill or Techo-Bloc bring the price higher. Our patios include 6–8" of compacted gravel base, polymeric sand joints, and a manufacturer warranty on the pavers. We don't cut corners on base prep — that's why our patios stay level through Chicago's freeze-thaw cycles.
A full backyard renovation in Chicago typically takes 2–6 weeks from start to finish. A patio install with plantings averages 7–14 days. Adding retaining walls, irrigation, or outdoor lighting extends the timeline. Full outdoor living spaces with multiple hardscape elements can run 4–8 weeks. We don't multi-job our crew — once we start your project, we're on-site daily until it's done. You'll have a clear timeline locked in before we break ground.
Pavers are individual units installed over a compacted base; concrete is a single slab poured in place. Pavers cost more upfront ($25–$40/sqft vs $10–$15/sqft for concrete) but last 30+ years, can be lifted and reset if needed, and don't crack across the surface. Chicago freeze-thaw cycles are brutal on concrete slabs — they almost always crack within 5–10 years. Pavers flex with the freeze and stay level. For Chicago patios, pavers are almost always the better long-term investment.
The best time to install sod in Chicago is mid-April through early June, or September through mid-October. These windows have cool temperatures and consistent rainfall, which helps roots establish before summer heat or winter dormancy. Sod can be installed in midsummer with extra watering, but rooting takes longer and stress kills are more common. Avoid late October installs — roots won't establish before frost and you'll lose the lawn over winter. We install fresh-cut Kentucky Bluegrass sod from local Illinois growers.
Chicago sits in USDA Hardiness Zone 6a, so plants need to handle winter temps down to -10°F. Reliable performers include hostas, hydrangeas (panicle and smooth varieties), boxwood, yew, juniper, daylilies, Karl Foerster grass, coneflowers, black-eyed Susans, and most native prairie species. Avoid plants rated Zone 7+ unless protected. Spring and fall are the best planting windows. Our landscape designers build planting plans matched to your sun exposure, soil type, and how the yard actually gets used.
Most residential landscaping work in Chicago doesn't require a permit. Plantings, sod, mulch, irrigation, lighting, and patios at grade typically don't need approval. Permits ARE required for: retaining walls over 4 feet tall, structures attached to the home, certain drainage modifications, and any work in public right-of-way (parkways). Tree removal also has specific rules depending on tree size and species. We handle the permit process when needed — pulled permits get itemized on your flat-rate quote so there are no surprises.
Standing water in Chicago yards is usually caused by improper grading (yard sloping toward the house instead of away), clay-heavy soil that doesn't drain, downspouts dumping water at the foundation, or compacted soil from foot traffic and construction. Fixes range from regrading and topsoil addition ($2,500–$6,000) to French drain installation ($3,500–$8,000) to full subsurface drainage systems for severe cases. Standing water near the foundation is the urgent one — it leads to basement flooding and foundation damage. We diagnose the cause during the walkthrough and quote the specific fix.
Landscape design from first walkthrough to finished plan typically takes 2–3 weeks at O'Brien Brothers. The first meeting is on-site — we measure, photograph, and listen to what you want the yard to do. From there, we produce a 2D layout, planting plan, materials list, and flat-rate construction quote. Revisions are included in the design fee. Complex designs with grading plans, lighting layouts, or irrigation schematics take longer. Design is the most important step — get it right and the build goes smoothly.
Yes. O'Brien Brothers Landscaping is fully licensed, bonded, and insured in the state of Illinois. We carry general liability and workers' comp on every crew member. Certificates available on request. We've been operating in Chicago since 2005 — 20+ years on the same North Side neighborhoods, 65+ five-star Google reviews, and an A+ track record. Insurance covers your property in the rare case something goes wrong on-site, which is why working with a licensed contractor matters.
Yes — paver patios, natural stone, poured concrete, brick walkways, retaining walls, fire pits, outdoor kitchens. Styles range from clean modern to traditional Chicago bungalow.

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