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Computerease

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Chicago IT Support & Managed Services for Local Businesses

Local Expertise. Enterprise-Grade Protection. Family-Owned Since 1984.

Computerease has supported Chicago businesses with hands-on IT service and CISSP-led cybersecurity for more than 40 years. Our team is based right here in the city, so when something goes wrong, you’re talking to a technician who knows your setup, not a call center reading from a script. We answer the phone with a real person, we treat clients like partners, and we support businesses of every size across Chicagoland with managed IT, cybersecurity, cloud, backup, and phone systems.

Computerease is a family-owned managed IT services provider supporting Chicago businesses from its downtown office at 205 N Michigan Ave, Suite 810. The company has served Chicagoland since 1984, offering managed IT support, CISSP-led cybersecurity, cloud services, VoIP, and backup and disaster recovery for businesses ranging from single-office practices to multi-location companies with their own internal IT staff.

Why Local Businesses Choose Computerease for IT Support

Chicago’s business landscape is not one thing. It’s law firms in the Loop, manufacturers in Elk Grove Village, healthcare practices in Arlington Heights, and fast-growing companies along the I-88 corridor in Naperville and Aurora. Each of those businesses runs on different software, faces different compliance pressure, and has a different tolerance for downtime.

Computerease works throughout Cook County, across DuPage County, and across the wider metro area, so we understand the connectivity challenges of a downtown high-rise as well as the shop-floor realities of an industrial park in Schaumburg. We’re not asking you to explain your business to us from scratch. We already know the vendors, the compliance requirements, and the kind of IT problems that show up most often in your industry.

As a second-generation, family-owned company with no outside investment, our incentives are simple: keep your technology running, answer the phone when you call, and keep you as a client for the long run. We’re not managing a private equity growth target. We’re managing our own name, and we treat every client relationship like a partnership, not a transaction.

Led by a CISSP-Certified Security Expert

Computerease is led by Ryan Haislar, CISSP, President and second-generation owner of the company his father founded in 1984. Ryan holds the Certified Information Systems Security Professional (CISSP) credential, one of the most rigorous security certifications in the industry, requiring both broad technical expertise and ongoing continuing education to maintain. Every cybersecurity strategy Computerease builds for a client in the Chicago suburbs or downtown is architected under that standard, not assembled from a generic template.

OUR CHICAGO STORY

Managed IT & Cybersecurity From a Family Business Rooted in Chicago

Ike Haislar started Computerease in 1984 to help businesses get more out of their technology without the runaround. Four decades later, that is still the job. Our downtown office on Michigan Avenue keeps us close to the companies we support, from offices in the Loop to plants and practices across the suburbs.

Today, Ryan Haislar, CISSP, leads the company as the second generation. He treats every client relationship as something the family name stands behind. For Chicago owners, that means a team that learns how your business works and plans ahead with you as you grow. For companies with their own IT staff, it means a partner who backs them up instead of taking over.

What usually happens is a business goes years with IT that only shows up when something breaks. Working with us looks different. The same people support your systems over time, so they remember how things are set up and why. Small problems get fixed before they turn into a bad week, and the repeat issues start to fade.

We also give straight answers. If an upgrade can wait a year, we'll say so. If something needs attention now, we'll explain why in plain terms and what it will cost. You get the full picture, so you can make the right call for your business.

”
"We plan every client's technology like we'll still be working together ten years from now. Across Chicagoland, a lot of them already have been."
Ryan Haislar, CISSP, President/CEO
Same Team. Same Relationship. Year After Year.
Since 1984TRUSTED FOR 40+ YEARS

Why Chicago Businesses Stay With Computerease

Over 40 Years Serving Businesses
Downtown Office on Michigan Avenue
Second-Generation Family Leadership
Cybersecurity Overseen by a CISSP
Coverage From the Loop to the Western Suburbs
Backup Support for In-House IT Teams
Practical AI Planning and Employee Training
ROOTED HERE
Four decades alongside Chicago businesses, with the same family still leading the way.

Managed IT Services in Chicago

Proactive Support Instead of Waiting for Something to Break. The old break-fix model, where you call your IT company only after something has already failed, costs local businesses real money in downtime and lost productivity. Our ConstantCare Managed IT Services program is built to catch problems before they interrupt your day.

What’s Included

  • 24/7/365 Network Monitoring — we watch your entire environment around the clock, from servers in a downtown data center to laptops in a home office in Aurora, so hardware failures and network issues get caught early.
  • Proactive Patching — unpatched software is one of the most common ways attackers get in. We keep every device and application current on a set schedule.
  • Unlimited Help Desk and Onsite Support — your team gets fast, friendly help from technicians who know your setup, not a ticket queue. Calls are always answered by a real person.
  • vCIO Strategic Planning — executive-level guidance to help you plan your technology budget and roadmap around your actual business goals.
  • Vendor Management — we become your single point of contact for internet, software, and hardware vendors, so you're not stuck on hold.

We’re deeply familiar with the local business ecosystem, including the connectivity challenges, common vendor relationships, and regulatory pressure facing companies throughout Cook and DuPage counties and across the Chicago suburbs.

Not Sure Where to Start? Let’s Talk IT

If you’re wondering whether your current IT setup is enough – or if there’s a smarter, more secure way to operate – let’s talk. We’ll guide you through your next step.
Schedule a 15 Minute Discovery Call

Business IT Support for Chicago | Local IT Support for Chicago Businesses

Managed IT Services

Total responsibility for your technology environment.

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Co-Managed IT Services

The force multiplier for your internal IT team.

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Cybersecurity

Advanced threat detection and 24/7 monitoring.

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AI for Business

AI strategy, training, and security for your business.

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Network Security

Layered defense for your business infrastructure.

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Cloud Computing

Scalable, secure, and accessible cloud infrastructure.

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Data Backup And Recovery

Business continuity and disaster recovery planning.

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IT Consulting & Implementation

Strategic guidance for digital transformation.

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VoIP & Communications

Crystal clear business communication systems.

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Managed Print Services

Optimized printing workflows and cost control.

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Chicago Cybersecurity Services

Chicago businesses face cybersecurity threats ranging from ransomware and business email compromise to phishing attacks that can disrupt operations and put sensitive information at risk. Computerease takes a CISSP-led approach to cybersecurity, helping businesses identify their biggest risks and choose the right protections. Our cybersecurity services are offered separately from Managed IT and tailored to each organization’s needs, using the Center for Internet Security (CIS) Critical Security Controls to guide our recommendations.

Core Cybersecurity Capabilities

  • Managed SIEM — real-time log collection and analysis across your firewalls, servers, and cloud apps to catch unusual activity fast.
  • Managed EDR — endpoint protection that watches behavior, not just known virus signatures, and can isolate a device the moment ransomware activity starts.
  • Managed SOC — a 24/7/365 security operations team that investigates and responds to threats, including nights, weekends, and holidays.
  • Managed Firewall & Firewall as a Service — configuration, patching, and monitoring of your network’s front door, with hardware included in some plans.
  • Managed SASE / ZTNA — secure remote access that replaces clunky, insecure VPNs for hybrid and work-from-anywhere teams.
  • Microsoft 365 Security Monitoring — watching for impossible-travel logins, suspicious forwarding rules, and other signs of a compromised account.
  • Multi-Factor Authentication — deployed through tools like Duo Security or hardware keys, to stop the majority of automated attacks.
  • Penetration Testing — ethical hacking to find weaknesses before someone else does.

For businesses in regulated industries, our CISSP-led team has direct experience helping healthcare providers across the Chicago suburbs meet HIPAA requirements, financial firms meet SEC and FINRA regulations, and government contractors meet CMMC requirements.

Book a Free Chicago Cyber Risk Assessment

AI Guidance for Chicago Businesses

Most local businesses aren’t looking to become AI companies. They just want to know what’s safe to use, what isn’t, and how to get value out of tools their teams already have access to. We help with that in a practical, right-sized way, including AI Readiness Assessments, employee AI training, secure Microsoft Copilot deployment, and AI Acceptable Use Policies that give your team clear rules instead of guesswork. The goal is secure, sensible AI adoption, not chasing every new tool that shows up in the news.

Co-Managed IT for Businesses with Internal IT Teams

If your business already has an in-house IT manager or a small internal team, our Co-Managed IT Services are built to add to what you have, not replace it. This model fits mid-sized companies throughout Chicagoland that need to scale their capabilities, bring in specialized expertise, or access enterprise-grade tools without hiring another full-time employee.

  • Bridge Skill Gaps — your internal team focuses on daily user support and projects, while we manage complex cybersecurity, cloud infrastructure, and 24/7 monitoring.
  • Backup and Escalation — when your IT manager is out sick, on vacation, or buried in a project, we cover as a tier-2 or tier-3 escalation point.
  • Enterprise-Class Tools — your team gains access to our ticketing, documentation, and security monitoring platforms.
  • Project Support — senior engineers to help plan and execute a cloud migration, office move, or infrastructure upgrade.

Chicago is home to a large number of regional and North American offices for companies headquartered elsewhere, across the United States and increasingly across Europe and beyond. Corporate IT may set the company-wide standards and manage the major infrastructure, but a local office still needs a partner who can handle day-to-day support, onsite troubleshooting, new-hire equipment setup, and the ongoing coordination that keeps a satellite office running smoothly. Computerease works alongside internal and international IT teams to provide that local, responsive layer of support while staying aligned with the standards headquarters has already set. Whether your headquarters is in London, Frankfurt, Toronto, or another U.S. city, our role is to be dependable local hands and eyes, working as an extension of the IT team you already have.

Cloud Solutions for Local Businesses

We manage Microsoft 365 and Google Workspace environments beyond just reselling licenses, configuring secure data-sharing policies and making sure your cloud data is properly backed up. For companies still running an aging, on-premise server, we handle migration to Microsoft Azure or Amazon Web Services, cutting the need for costly hardware refreshes and improving reliability. See our full Cloud Services offering for more detail.

VoIP Business Phone Systems

Our cloud-based VoIP systems let your team stay connected from a desk phone, a computer, or a mobile app, using the same office number wherever they’re working. It’s a practical fit for hybrid teams split between downtown offices and homes across the suburbs.

Data Backup and Disaster Recovery for Chicago Businesses

A fire, flood, or ransomware attack can take out your office and your servers in the same afternoon. Without a real continuity plan, that’s a business-ending event, not just a bad week.

  • Automated, Frequent Backups — incremental backups as often as every hour, to limit how much data could ever be at risk.
  • Hybrid Cloud Backup — data backed up locally for fast recovery, then encrypted and replicated to secure off-site data centers.
  • Rapid Recovery & Instant Virtualization — a virtual copy of a failed server can be spun up locally or in the cloud within minutes.
  • Regular, Verifiable Testing — we run recovery drills so we know backups will actually work before you ever need them.

Need IT Help?

Tell us what’s going on with your IT. No hard sales, no pressure—just helpful guidance from our team.
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INDUSTRY EXPERTISE

Specialized IT Support for Chicago’s Key Industries

Every industry has its own technology challenges and compliance requirements. We don’t offer one-size-fits-all solutions. Our team has decades of experience providing tailored IT support for businesses across Chicago’s diverse economic landscape.

IT Services for Healthcare & Medical Practices

IT Services for Healthcare & Medical Practices

From small suburban practices to clinics inside larger hospital networks, we keep EHR and Practice Management systems running, your network HIPAA compliant, and patient data secure.
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IT Solutions for Financial & Accounting Firms

IT Solutions for Financial & Accounting Firms

From accounting firms in the Loop to wealth management firms across the suburbs, we implement security measures built for regulated data and help firms meet FINRA and SEC requirements.
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Managed IT for Manufacturing & Logistics

Managed IT for Manufacturing & Logistics

Chicago is a major manufacturing and logistics hub. We support ERP systems, inventory platforms, and industrial control systems, backed by disaster recovery plans built to limit production downtime.
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Engineering & Construction IT Support

Engineering & Construction IT Support

We advise on the right technology for both office workstations running AutoCAD and rugged laptops in the field, backed by nearly 40 years of experience supporting engineering and construction firms.
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IT Support for Chicago Law Firms

IT Support for Chicago Law Firms

We support case management software, document management systems, and e-discovery platforms for local law firms, with an eye toward the confidentiality and uptime standards required under ABA ethical rules.
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Small & Medium Business IT Support

Small & Medium Business IT Support

A responsive, reliable IT partner can end the cycle of recurring problems for a growing business. We support your business with all technology needs backed by our 100% money back guarantee.
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Serving Businesses Across Chicagoland

Computerease supports businesses throughout the city and the surrounding suburbs, with both remote and onsite support available wherever you’re located. Service area spans Cook County, DuPage County, Kane County, and Lake County.

Chicago & Northwest Suburbs

Western Suburbs & Beyond

Computerease vs. National IT Providers

Comparison Point National IT Providers Computerease
Local presence
Regional or national call center, often outside Illinois
Office in downtown Chicago, with technicians who work in the local business community every day
Response time
Support tickets often route through multiple tiers before reaching a technician
Critical, system-down issues aim for a response in 15 minutes or less
Security leadership
Security often sold as a separate add-on package
CISSP-led security strategy, 24/7 SOC monitoring
Relationship model
Multi-year agreements or rigid contract terms are common
Long-term partnership with a one-year initial agreement, then month-to-month flexibility
Ownership
Often owned by a private equity firm or larger holding company
Second-generation, family-owned since 1984, no outside investment
Strategic guidance
IT strategy often limited to ticket resolution
vCIO planning tied to your actual business goals

What Our Clients Say

I have been with Computerease for many years. They have a great team of I.T. techs, whether it is on the phone or coming to my office. They are fast and efficient.

Chris Gianino

Simple Moves

We are a small business and have been a Computerease client for years. I highly recommend their services for large and small firms. Always extremely efficient with their response times and very knowledgeable on all things computers/systems!

Erin Morris

AAIC

I have to say, these guys and girls are the BEST! They are there for every question and issue, always with the perfect resolution. We reach out to them often just exploring options with our systems. Computerease always makes our lives easier! We love them!!

Chris Sigman

Inner Wellness

Deep knowledge of systems hardware, Microsoft OS and many software platforms. Very responsive when we have issues. Computerease never leaves us hanging. A true partner for a company like ours that does not have in-house IT support. I give them my highest recommendation.

Bob Barenholtz

St. Louis Tag

Dan was incredibly kind, patient, and helpful — hands down the easiest laptop transition I’ve had in over 20 years! I was able to work all day while he handled everything, and he also got our conference room tech running smoothly. Everything feels easier and better than our old setup — the Computerease team is really good.

Kelly Crabtree

Columbus Capital Partners

Not Ready To Call Us Just Yet?

If you’re not ready to call just yet, check out our free IT Buyer’s Guide. This FREE report is your comprehensive guide to avoid hidden fees and bloated contracts that other IT support companies in Chicago claim that you “absolutely need.”

This report is for any Chicago business owner or administrator looking for the best IT company. It will save your time and money during your search for a new business IT support company. Fill out the form and you’ll get your FREE copy instantly

Directions to Computerease’s Chicago Office

Computerease IT Support of Chicago
205 N Michigan Ave, Suite 810
Chicago, IL 60601
Phone: (312) 463-4545
Hours: Monday–Friday, 8:30 AM–5:00 PM, with support available 24/7/365.

Computerease IT Support of Chicago is located on 205 N Michigan Ave, Suite 810, Chicago, IL. From Chicago Midway International Airport (MDW) get on I-55 N/Stevenson Expy, and head south on S Cicero Ave. Then make a U-turn at W 59th St, and turn right onto the Interstate 55 N/Stevenson Expy ramp to Chicago. Next continue on I-55 N/Stevenson Expy, and take Exit 292A to S Franklin St. At this point take the Franklin St exit from IL-110 E, and merge onto I-55 N/Stevenson Expy. After that take exit 292A to merge onto I-90 W/I-94 W toward W Ryan Expy/Wisconsin, and use the right 2 lanes to take exit 51H for I-290 W. Afterwards, keep right at the fork to continue on Exit 51I, follow signs for Ida B Wells Dr and merge onto IL-110 E. Next take the Franklin St exit, and keep right, follow signs for Franklin St and merge onto S Franklin St. Then continue on S Franklin St. Drive to W Madison St, and merge onto S Franklin St. At this point turn right onto W Calhoun Pl, and turn right at the 1st cross street onto N Wells St. Finally, turn right at the 1st cross street onto W Madison St, and Computerease IT Support of Chicago will be on the right.

For additional questions you can call us at (312) 463-4545

Schedule Your Free Chicago Network Assessment

If you’re dealing with slow support, recurring technical problems, or growing concerns about cybersecurity, it may be time to look at a better option. Our free network assessment includes:

  • A full review of your current IT infrastructure and security posture.
  • A scan for vulnerabilities, misconfigurations, and compliance gaps.
  • A check on the integrity of your current data backup and recovery systems.
  • A clear, easy-to-understand report with next steps.

Book Your Free Chicago Network Assessment

Frequently Asked Questions About Chicago IT Support

Key Takeaways

  • Computerease has supported Chicagoland businesses since 1984 as a second-generation, family-owned company.
  • Security strategy is CISSP-led and built around the CIS Critical Security Controls framework.
  • Critical, system-down support requests are targeted for a response in 15 minutes or less.
  • Clients begin with a one-year agreement, then continue month to month as long-term partners—not tickets.
  • Services cover managed IT, cybersecurity, cloud, backup and disaster recovery, VoIP, co-managed IT, managed print, and practical AI guidance, for businesses across Cook, DuPage, Kane, and Lake counties.