5 Best Gutter Cleaners in Chicago (2026)

Independently ranked by our review of ratings, reviews and reputation · How we chose

By Brad Smith, Home Services Expert · ✓ Data verified July 2026 · 8 min read

Clogged gutters in Chicago tend to surface at the worst time, right after a storm dumps leaves and debris onto a roof nobody has checked all year, which is when most people start searching for gutter cleaners in Chicago. The companies here have racked up more than 3,100 Google reviews combined, and while ratings range from 4.4 up to a perfect 5.0, the size of that review base varies just as much, which says a lot about how long each has been doing this at scale.

Short answer: Gutter Repair & Replacement Chicago (Adrian's) holds a perfect 5.0 across 424 reviews, praised for fast quotes and fair pricing on both cleaning and repair jobs. Prime Time Window & Gutter Cleaning is the most-reviewed name on the list at 1,657 reviews, running since 1996, though its 4.4 rating trails the other four. One reviewer of Prime Time's own service reported a quote of roughly $225 to $240 for a two-story house with two clogged downspouts, a useful real-world data point rather than an official rate card.

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1. Prime Time Window & Gu…
2. Gutter Repair & Replac…
3. Guaranteed Gutters Inc
4. Gutter Enriquez LLC
5. My Window Washing and…
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Chicago's Gutter Cleaners, Compared

#	Business	Rating	Reviews	Best for
1	Prime Time Window & Gutter Cleaning	4.4 ★	1,657	Established, high-volume provider	View ›
2	Gutter Repair & Replacement Chicago – Adrian’s	5.0 ★	424	Fast quotes and repairs	View ›
3	Guaranteed Gutters Inc	4.9 ★	389	Gutter guards and long-term maintenance	View ›
4	Gutter Enriquez LLC	4.9 ★	351	Gutter installation and correction	View ›
5	My Window Washing and Gutter Cleaning	4.9 ★	329	Combined gutter and window service	View ›

5 Best Gutter Cleaners in Chicago (2026)

Our top picks, reviewed

#1 Overall🕑 Open 6 days/wk↩ Responds to reviews

Prime Time Window & Gutter Cleaning

4.41,657 Google reviews

Prime Time Window & Gutter Cleaning has served the Chicagoland area since 1996, offering residential and commercial window washing, gutter cleaning and pressure washing. The company reports more than 40,000 customers served and continues expanding into northern Illinois, with technicians handling window, gutter and skylight work as a combined service.

What people praise

Thorough gutter clean-outs that reviewers say revealed a surprising amount of built-up debris
Technicians communicate clearly and leave the property clean afterward
Transparent about additional per-downspout fees for extra clogged sections
Long operating history, in business since 1996

Worth knowing

Some reviewers report pricing surprises when add-on services like window frames were not clearly scoped upfront
Lowest rating on this list, with a meaningful share of critical reviews mixed among the positive ones

Reputation scorecardrank in Chicago

Rating4.4 / 5

Review volume1,657 · 97th

Confidencehigh

Recency6 weeks ago

Info completenesssite · phone · hours

Rating breakdown76% 5-star

✓ VerifiedSource: Google

Our take: The most-reviewed and longest-running name here, useful for combined gutter-and-window jobs, but confirm the full scope and price for every add-on before the crew starts, since that is where reviewers report the most friction.

Website +1800-480-1360 Directions

1806 W Cuyler Ave #3A, Chicago, IL 60613

#2🕑 Open 7 days↩ Responds to reviews

Gutter Repair & Replacement Chicago – Adrian’s

5.0424 Google reviews

Gutter Repair & Replacement Chicago (Adrian's) is a Chicago gutter and roofing contractor covering gutter repair, replacement, cleaning and seamless gutter installation, alongside general roofing and siding work. Reviews describe the owner, Adrian, personally following up on quote requests, often the same day, and crews completing both small repairs and larger roofing jobs quickly.

What people praise

Perfect rating across all 424 reviews on Google
Fast turnaround on quotes, frequently the next morning after a request
Reviewers who compared multiple quotes describe the pricing as fair to competitive
Handles everything from a single downspout repair to a full roof replacement

Worth knowing

Smaller review base than Prime Time, though every review here is positive
Roofing and gutter work both handled by the same crew, so availability may vary by season

Reputation scorecardrank in Chicago

Rating5 / 5

Review volume424 · 92th

Confidencehigh

Recency3 months ago

Info completenesssite · phone · hours

Rating breakdown98% 5-star

✓ VerifiedSource: Google

Our take: The highest-rated name on this list and the strongest pick if responsiveness and fair, comparison-tested pricing matter most to you.

Website +1872-258-8417 Directions

2004 W 18th Pl, Chicago, IL 60608

#3🕑 Open 6 days/wk

Guaranteed Gutters Inc

4.9389 Google reviews

Guaranteed Gutters Inc is a Chicago gutter cleaning, repair and installation company that also installs gutter guards and offers roof maintenance. The company brands itself around long-term customer relationships, with several reviewers describing years of repeat annual or biannual service rather than a single one-off job.

What people praise

Multiple reviewers describe being repeat customers over several years
Clear communication and detailed billing after each visit
Willing to return promptly to fix any part of the job that was missed
Gutter guard installations come with a long transferable warranty

Worth knowing

Smaller share of five-star reviews than the top two names on this list
Best suited to homeowners planning ongoing maintenance, not just a one-time clean

Reputation scorecardrank in Chicago

Rating4.9 / 5

Review volume389 · 87th

Confidencehigh

Recency8 weeks ago

Info completenesssite · phone · hours

Rating breakdown93% 5-star

✓ VerifiedSource: Google

Our take: A strong pick if you want a long-term relationship for annual or biannual gutter maintenance rather than a single cleanout.

Website +1773-685-9556 Directions

5900 W Eastwood Ave, Chicago, IL 60630

#4🕑 Open 7 days↩ Responds to reviews

Gutter Enriquez LLC

4.9351 Google reviews

Gutter Enriquez LLC is a Chicago company, in business since 2010, specialising in gutter installation, repair, replacement and cleaning, along with roofing and siding work. Reviews frequently describe the crew diagnosing installation problems from other contractors, such as gutters pitched incorrectly, and correcting them alongside the original service request.

What people praise

Crews diagnose and fix underlying installation problems, not just surface symptoms
Transparent, reasonable pricing repeatedly praised across reviews
Handles corner repairs and smaller jobs alongside full installs
Consistent five-star feedback on communication and follow-through

Worth knowing

Slightly smaller review base than the two most-reviewed names on this list
Company also handles roofing and siding, so scheduling may depend on season

Reputation scorecardrank in Chicago

Rating4.9 / 5

Review volume351 · 76th

Confidencehigh

Recency3 weeks ago

Info completenesssite · phone · hours

Rating breakdown95% 5-star

✓ VerifiedSource: Google

Our take: A dependable choice, especially if you suspect an underlying installation issue rather than just needing routine debris removal.

Website +1773-952-0517 Directions

1816 S Trumbull Ave, Chicago, IL 60623

#5🕑 Open 6 days/wk↩ Responds to reviews

My Window Washing and Gutter Cleaning

4.9329 Google reviews

My Window Washing and Gutter Cleaning has served Chicago's Northwest Side neighborhoods since 2003, offering window washing, gutter cleaning, power washing and solar panel cleaning from a local office rather than a call center. The company highlights experience with Chicago's distinctive housing stock, including greystones, courtyard buildings and classic bungalows.

What people praise

Technicians accommodate scheduling conflicts and tight time windows
Transparent, upfront pricing mentioned consistently across reviews
Local office and local knowledge of Chicago's older housing styles
Handles gutters, windows and power washing in a single visit

Worth knowing

Slightly lower review volume than the top three names on this list
Best suited to combined jobs rather than a gutter-only service call

Reputation scorecardrank in Chicago

Rating4.9 / 5

Review volume329 · 66th

Confidencehigh

Recency8 weeks ago

Info completenesssite · phone · hours

Rating breakdown94% 5-star

✓ VerifiedSource: Google

Our take: A convenient, well-reviewed option if you want gutters, windows and exterior power washing handled by one local crew in a single appointment.

Website +1773-377-4600 Directions

4747 W Peterson Ave Ste 407, Chicago, IL 60646

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How we score

Every number on this page comes from public Google data on the date shown, not from opinion or payment. Rating is the business’s live Google star average. Review volume is how many customers have rated them, ranked against other Chicago gutter cleaners. Confidence weighs the rating by that volume, so a 4.9 from hundreds of reviews carries more weight than the same score from a dozen. Recency reflects how recently customers are still leaving reviews. No business can pay to change these numbers.

How much does gutter cleaning cost in Chicago? (2026)

None of these companies publish a standard rate card, so pricing depends on house size, roof pitch and number of downspouts. One reviewer of Prime Time’s service shared a real example: a quote of $225.75 for a two-story, roughly 2,300 square-foot house, with the final cost coming to $238.35 after two plugged downspouts needed extra attention. Treat that as a single real data point, not a citywide rate, and always get your own written quote.

Serving all of Chicago

The gutter cleaners above serve Chicago’s neighborhoods and the Chicagoland metro, including the Northwest Side, the West Side and surrounding suburbs like Arlington Heights and Crystal Lake. Searching for a gutter cleaner near me? Every listing below shows a live phone number and website so you can check current availability.

What to ask before you hire a gutter cleaner

Is the quote a flat rate, or does it change based on the number of downspouts cleared?
Do you inspect for underlying issues, like incorrect pitch or damaged sections, as part of the visit?
Is a roof or gutter inspection included for free, or is that a separate charge?
Do you offer gutter guard installation, and what warranty comes with it?
Will you provide the final price in writing before starting the work?

Frequently asked questions

How did you choose these gutter cleaners?

We started from every gutter cleaner in Chicago with a public Google presence, then ranked by rating, review volume, consistency and recency. See How we score above.

Are these rankings paid?

No. Rankings come from the public Google data in the scorecard. A business can pay to be a Featured Partner, which adds a badge and top placement, but that never changes another business’s score or position on the underlying data.

How often is this updated?

The data carries a verified date (July 2026 on this page). We refresh listings periodically so ratings and review counts stay current.

How often should I clean my gutters in Chicago?

Most homeowners clean gutters at least once or twice a year, typically after leaves fall and again before spring rains. Homes near a lot of trees may need more frequent visits.

Do any of these companies also handle gutter repair or replacement?

Yes. Gutter Repair & Replacement Chicago (Adrian’s) and Gutter Enriquez LLC both handle repair and full replacement alongside cleaning, and Guaranteed Gutters Inc also installs gutter guards for longer-term protection.

The bottom line

Gutter Repair & Replacement Chicago (Adrian’s) is the safe default on its perfect rating and fast, fair quotes, while Prime Time is the name with the longest track record if you want gutters and windows handled together. Whoever you call, get the per-downspout pricing confirmed in writing before the crew starts.

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