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.
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Chicago: 312-554-7550
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St. Louis : 314-432-1661
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Metro East IL : 618-346-8324
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Central IL : 217-528-0500
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.
Book Your Free Chicago Network Assessment – Call (312) 463-4545
Why Chicago Businesses Choose Computerease
- CISSP-Led Security every security strategy is built and reviewed by a Certified Information Systems Security Professional, not a call-center script.
- Second-Generation, Family-Owned — serving the local business community since 1984, with no outside investment or private equity ownership.
- 1-Year Initial Agreement, Then Month-to-Month Flexibility — after the first year, clients continue month to month because we earn the relationship through responsive support, reliable service, and a real partnership.
- Fast Response — for critical, system-down issues, we aim to respond in 15 minutes or less.
- Nationally Recognized — named to the Inc. 5000 and the CRN MSP 500.
Quick Answer
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.
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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.
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.
Local Chicago IT Service Management
Work From Home
Keep your entire team productive and secure working from any location.
Microsoft 365
Utilize the power and functionality of Microsoft 365 for your business.
IT Helpdesk
Tech experts are available 24/7/365 to help address any problems.
Managed Print Services
Printer fleet management without the surprise supply costs.
AI for Business
Practical guidance on where AI tools actually fit your workflows, and where they don't yet.
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.
Chicago Cybersecurity Services
Chicago’s economy makes it a target. Ransomware, business email compromise, and phishing campaigns can shut a company down for days. Computerease integrates security into every layer of service instead of selling it as a separate add-on, following the Center for Internet Security (CIS) Critical Security Controls, a widely used framework for prioritizing the security work that actually reduces risk.
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.
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.
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.
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.
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.
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
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.
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.
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.
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.
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.
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.
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.
- Chicago: all neighborhoods, including the Loop, River North, Lincoln Park, and Hyde Park.
- Naperville & Aurora: businesses along the I-88 corridor.
- Schaumburg & Elk Grove Village: the dense concentration of commercial and industrial businesses in the northwest suburbs.
- Arlington Heights & Palatine: professional service firms in the northwest suburbs.
- Downers Grove & Oak Brook: corporate offices in the western suburbs.
- Carol Stream & Addison: manufacturing, distribution, and service businesses.
- Itasca, Rosemont & Bensenville: the O’Hare-area commercial corridor.
- Also serving: Bolingbrook, Des Plaines, Franklin Park, Niles, Plainfield, Rolling Meadows, Wheeling, Wood Dale, and Woodridge.
Service area spans Cook County, DuPage County, Kane County, and Lake County.
Computerease vs. National IT Providers
Computerease | National IT Providers | |
Local presence | Office in downtown Chicago, with technicians who work in the local business community every day | Regional or national call center, often outside Illinois |
Response time | Critical, system-down issues aim for a response in 15 minutes or less | Support tickets often route through multiple tiers before reaching a technician |
Security leadership | CISSP-led security strategy, 24/7 SOC monitoring | Security often sold as a separate add-on package |
Relationship model | Long-term partnership with a one-year initial agreement, then month-to-month flexibility | Multi-year agreements or rigid contract terms are common |
Ownership | Second-generation, family-owned since 1984, no outside investment | Often owned by a private equity firm or larger holding company |
Strategic guidance | vCIO planning tied to your actual business goals | IT strategy often limited to ticket resolution |
What Client’s Say About Us
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 MovesWe 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
AAICI 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 WellnessDeep 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 TagDan 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 PartnersNot Ready To Call Us Just Yet?
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Your Partner for Chicago IT Infrastructure Support
For fast response times, Computerease is perfectly situated to provide businesses in Chicago world class IT Services. Our office is available to provide a wide range of services to local businesses. With our IT Helpdesk Services, your team has 24/7 IT Support, no matter when and where they work. If your business finds itself looking at a disaster, you want Chicago's most reliable IT Support Company. As Chicago’s IT experts, business owners have trusted us with all their IT support needs. We work alongside business owners to design and implement a comprehensive IT strategy, keeping cyber security protections at the forefront. Contact us today to start your journey towards headache free IT support.
Directions to Computerease’s Chicago Office
Computerease IT Support of Chicago is located on 200 West Madison, Suite 2100, 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, adn 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 Franklinn 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.
Frequently Asked Questions About Chicago IT Support
We work with small companies with just one or two employees up to large companies with hundreds of team members. All of our solutions are enterprise-grade and built to scale.
We are committed to fast response times. For critical, system-down issues, we aim to respond in 15 minutes or less. Our help desk is staffed by live technicians, so you’re not navigating a phone menu.
Yes. We set up secure VPNs and modern remote-access alternatives, manage mobile devices, and make sure your remote team members, whether downtown or across the suburbs, have reliable access to company resources.
Pricing is typically a flat, predictable monthly fee based on the number of users and devices we support. This model covers proactive maintenance, monitoring, and help desk support. We provide a custom, transparent quote with no hidden fees.
Yes. Our CISSP-led team has deep experience navigating regulatory requirements. We can perform a gap analysis, implement the necessary technical controls, and provide documentation to help you pass an audit.
When a critical piece of hardware fails, you need a partner who can be onsite in your Naperville office or Schaumburg facility right away. A national call-center provider can’t match that. As a local, family-owned business, we’re invested in the success of the local business community, and we build relationships that last, not just service tickets.
Key Takeaway
- 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.