“ReachOut is on top of the newest technology and communicates this information to my team. I would highly recommend ReachOut IT to other firms.”
Chicago IT Outsourcing Services
Get the technology, services, and expertise your business needs to thrive
Support your in-house team or fully outsource IT. Maximize value with services tailored to what drives your business forward.
Choose from flexible service levels that align with your needs, not one-size-fits-all boxes.
Lead with security every time. Our Cybersecurity-First approach is built into every engagement, never tacked on as an extra.
Most issues are resolved in 15 minutes or less. Get guaranteed sub-60-second response times and direct Level 2 access with ReachOut ONE.
Pay one flat monthly rate. No onboarding fees, no hidden costs, and zero surprise upcharges, even during upgrades or busy periods
Request a Quote for IT Outsourcing in Chicago
Outsource Your IT Services in Chicago to a Trusted Partner
Hand off your IT headaches and gain a partner who puts outcomes, security, and your growth first–every single day.
Mark McNabola
McNabola Law Group
“I know that if I have a problem and call that the problem will be completely resolved. I enjoy speaking to Jovy to get my problems resolved. She is very patient and kind with me especially since I seem to get confused with the processes involved with the computer”
Sandy
McNabola Law Group
“I have dealt with ReachOut for the past few years & have had nothing but successes. They always maintain professionalism in their field of work.”
Chris Shields
Navitas Capital
“Always a quick response from your team. ReachOut follows up quickly and stays on top of issues until they are completely resolved. Great job!”
Maureen Rubino
Goldberg & Schulkin Law Offices
“House-on-fire emergency handled by Jovy with grace and speed. So appreciative of the helpfulness and knowledge! She literally saved the day.”
Maggie Mayer
Kinnally Flaherty Krentz & Loran, P.C.
“Mel was great. She knew the urgency and understood that we had had issues with this client previously and worked with me to provide all the info to be proactive and inform them of their errors and how to prevent in the future. Great job! Thank you!”
Jamie Burgeson
Creative Colors Intl
“Jorel was maybe too fast and gave me no excuse for getting back to work :). Wonderful as always!”
Marijo Kleinfelder
Kids Can Do
About ReachOut’s IT Outsourcing
We’re a publicly accountable, security-first partner led by CEO Rick Jordan, a national authority on cybersecurity and business strategy.
With a team built for both rapid response and long-term results, we make IT simple, secure, and aligned with your growth.
OUR CLIENTS:
HOW WE HELP
Secure, Simplify, and Save with IT Outsourcing in Chicago
Cybersecurity-First
Lock down your systems from day one, with proactive 24/7 monitoring, threat detection, and security reviews. Shield your business with secure backups, employee training, real-time response, and more.
Simplify Compliance
Turn compliance into a competitive advantage. Stay contract-ready, pass audits the first time, and keep focus on your business. Map your systems to major frameworks, including HIPAA, CMMC, and NIST.
Predictable Pricing
Commitment should go both ways. That’s why clients who choose a 3- or 5-year agreement unlock exclusive rates and premium support packages. Get full access to our services at a rate you can rely on.
Full-Service IT Outsourcing Company in Chicago
Tap into technology solutions designed for your business’s long-term growth, not just quick fixes or one-off responses.
Managed IT
Move past reactive support. Each plan is custom-built to keep your business running efficiently, delivering results that last.
Cybersecurity
Stay protected with 24/7 defenses and ongoing training that keeps threats out and your team prepared for anything.
IT Support
Access expert help in under a minute. Get your issues solved fast so your team never loses momentum.
Cloud
Take control of your cloud. Gain secure, cost-effective solutions that scale seamlessly as your business expands.
IT Helpdesk
Get the answers you need, right when you need them. Routine questions handled instantly, and tough issues solved by real engineers.
Network Support
Trust a network that’s always on. Reliable, secure, and built to support your business without interruption.
IT Consulting
Get guidance that drives decisions. Leverage deep expertise and proven strategy to plan your IT future with confidence.
Compliance
Stay audit-ready at all times. We map your risks, manage documentation, and keep your business aligned with every requirement.
Digital Transformation
Upgrade your workflow. Replace outdated processes and technology with streamlined systems that help your business move faster.
Awards & Certifications
Proven Chicago IT Outsourcing
15 Years
Supporting companies across North America
6,000+
End users rely on us for support and cybersecurity
90%
Tickets are responded to in just 9 minutes
Elevate Your Technology, Unlock Your Business’s True Potential
Most IT outsourcing stops at keeping the lights on. We take full accountability for your business results. Your goals drive every recommendation and every service we deliver.
Responsibility is built in. If we don’t fix the issues or deliver the outcomes we promised, you get your money back. No finger-pointing, no excuses, just real guarantees you can count on.
We don’t just maintain what you have. Our team actively looks for ways to improve your systems, eliminate friction, and help your team work smarter at every turn.
From AI-driven efficiencies to unlocking contractual opportunities through compliance, we turn technology into your advantage.
ReachOut IT
IT Outsourcing Firm in Chicago
- 73 W Monroe St Suite 607, Chicago, IL 60603, United States
Break Free From Your Old IT Contract
ReachOut covers up to 12 months of your existing agreement, so you can upgrade your IT without waiting or paying double
Comprehensive IT Services Near You
Local experts, full-service support, and fast solutions. Available where and when your business needs them most.
Frequently Asked Questions
How do you help my business grow, not just fix problems?
We look beyond quick fixes. Your business gets proactive guidance, quarterly business reviews, and tech stack refreshes that keep your IT in sync with your growth. Our advisors find new efficiencies with AI and automation, help you plan for the future, and remove barriers before they become roadblocks, so your technology is always an asset, never a bottleneck.
Do I need to sign a long-term contract to get started?
No. Most of our services come with no long-term commitment requirements; you can start with full support right away. If you do choose a multi-year agreement, you’ll access better pricing and premium support, but the choice is always yours. We believe you should stay for the outcomes, not because you’re stuck in fine print.
Is cybersecurity included in every service plan?
Absolutely. Cybersecurity-First isn’t just a phrase, it’s built into every plan from the start. You get 24/7 monitoring, regular threat assessments, employee training, secure backups, and proactive risk mitigation. No matter your plan or business size, protection is always included, not added on.
We deploy comprehensive cybersecurity across your company, protecting devices, servers, applications, cloud systems, and more.
Can you support both remote and on-site needs?
Yes. We blend seamless remote troubleshooting with hands-on, local service for any issue that requires a technician on-site. Our local experts are ready to handle hardware installs, urgent repairs, and preventative maintenance whenever you need it, ensuring nothing is missed or delayed.
Issues are seamlessly escalated for on-site support, saving you the hassle of having to call another team or argue with a chatbot.
How do you ensure compliance with industry regulations?
We handle compliance from the ground up, mapping your systems to standards like HIPAA, CMMC, and NIST. Our experts identify gaps in your people, processes, and technology, and help you build audit-ready documentation. Ongoing oversight, policy reviews, and remediation support keep you ahead of regulatory changes, so you’re always prepared for audits or contract renewals.
Outsourced IT Services in Chicago
Rest easy with a 30-day money-back guarantee if we don’t fix your core IT or security issues—no strings, no questions.
Speak to real experts in under 60 seconds, never a dispatcher or scripted call center, always a technician who can help, right away.
Count on CEO-led visibility. Rick Jordan’s leadership means public accountability, national credibility, and a real face behind every promise.
Experience the strength of a national brand with the personal service of a team that knows your business by name.
Build a strategic partnership with a dedicated tech advisor focused on planning, security, and keeping your systems running without the jargon.
Request a Quote from Our IT Outsourcing Company
We Value Your Feedback!
Love our service? Tell us with a Google review!
