Chicago IT Helpdesk Services

Outsource your IT help desk for rapid resolutions to your most pressing IT issues.

Get Reliable IT Help Desk Services in Chicago From Experienced Professionals

Minimize downtime by leveraging IT help desk outsourcing to resolve IT issues quickly.

Why choose OSG for IT help desk services?

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IT Helpdesk in Chicago

Our well-trusted and longstanding technology partners

Chicago's Trusted IT Services:
What Our Clients Are Saying

We've had an outstanding experience with Attentus. Brandon P., our NetAdmin, is proactive, attentive, and truly invested in our success. He consistently checks in, anticipates needs, and ensures we're supported at every level. What really stands out is that Brandon goes the extra mile to troubleshoot issues thoroughly and stays with them until they're fully resolved. We never feel like tickets are just being closed — he makes sure the solution actually works for our team.
Sean is always friendly, approachable, and completely solution-oriented. He makes even frustrating I.T issues feel manageable and keeps things moving quickly.
Logan has been invaluable when it comes to more complex projects. He approaches challenges thoughtfully, finds clear and effective solutions, and is patient with questions — explaining things in a way that even less tech-savvy folks can understand.
Joel O., our vCIO, has been a steady leader overseeing our biggest challenges and the overall health of our systems.
The team is consistently responsive and helpful, and their customer service truly stands out. Choosing Attentus is one of the best decisions we've made — they give us confidence and peace of mind every day.
Highly recommend!

We completely outsourced our IT department to Outsource Solutions Group, Inc. They handle all the security and critical patching to our infrastructure as well as all help desk support. We also procure all our hardware needs through Outsource. OSG is extremely responsive to our needs, handles tickets with care and timeliness too. We appreciate everything they do for us and would recommend their services to any business looking for an IT provider you can trust

We started with OSG a few years back when we had issues with our former IT company. They were professional and quick to serve us. Since that day we have loved the relationship that we have with all the staff at OSG. Their customer service is outstanding. I wish we would have switched to them sooner and I would HIGHLY recommend them!

Outsource IT Group has taken the time to learn our business, serve as a trusted partner, and provide a level of expertise that allows us to effectively allocate human resources to other critical services. In addition to providing us with technical and hardware support, the strategic quarterly meetings have helped us to grow as an institution through the implementation of new technologies and processes. Newly instituted services include increasing internet speed and stability, the pending implementation of RFID, and a successful transition to the Microsoft Phone System for unified communication. We would highly recommend their services to any organization looking for innovation and creativity.

Outsource Solutions Group

IT Help Desk Services in Chicago

1016 W Jackson Blvd PMB #444, Chicago, IL 60607, United States

205 Michigan Ave Suite 810,
Chicago, IL 60601, United States

Our Outsourced Help Desk Services in Chicago At a Glance

Consolidate Your Help Desk Needs

Fragmented helpdesk services can cause confusion when your team encounters user issues.

Who should they call for network support versus hardware support? How many invoices will your accounting team need to manage as a result?

We provide all the IT helpdesk services you need under one roof, so you only need to contact one vendor and pay one monthly invoice. This significantly simplifies your business operations.

Quick to Respond

Why wait for support when you need to get your business back online now? Our remote helpdesk services include after-hour support and a superior ticketing system at no additional cost.

Being able to reach our helpdesk team at any time ensures you are always open for business.

Whether you need to keep your chat bots working after-hours or process online payments, we’ve got you covered. Get the fast response time your business deserves.

Minimize System Downtime

Staying connected plays a crucial role in serving your customers, whether you serve them in-person or remotely. Connectivity affects everything from customer service chats to payment processing and employee remote access.

If your business experiences disruptions in service or connectivity, our support team will work quickly to:

Identify the affected components
Determine the cause of the outage
Deploy field technicians, if necessary
Resolve the issue remotely, if possible

Enhance Your First Line of Defense

When you choose OSG for managed IT services, cybersecurity is integrated with helpdesk services.

While helpdesk support is usually a reactive service, IT security should always prioritize proactive measures.

With this goal in mind, we provide the following integrated cybersecurity services:

Firewall management
24/7 system monitoring
Patch and update management
Remediation of potential threats
Access to secured service desk software

Case Studies

PROtential

PROtential is a marketing and consulting services firm, assisting with Brand development, sponsorship development, evento management, and more. They research and facilitate marketing opportunities for their clients to support their endeavors.

Phoenix Leather Goods, LLC

Phoenix Leather Goods is an online retailer that sells clothing accessories on two direct web stores as well as online marketplaces. They originally started selling only leather products, but have expanded in the past few years to offer sleepwear and branded clothing items. As an organization that primarily does business online, they rely on their IT to keep track of their inventory, process sales, and more.

Greenseed Contract Packaging

Is your IT support short-sighted? We help clients like this manufacturing firm in Batavia, Illinois to plan out their IT Budget months in advance, avoiding surprise while completing projects.

G&D Property Management Inc.

G&D Property Management Inc. manages community associations for a range of clients, including condominium, townhome and homeowner associations. Their team Works closely with associations staff and members including Board of Directors and Homeowners to provide a range of programs and services.

Big Shoulders Fund, Chicago

Big Shoulders Fund provides financial support to help working-class families attend Catholic schools in Chicago’s inner city communities. For over 10 years they have been a client of Outsourced IT Solutions Group, throughout which we have helped Big Shoulders Fund upgrade systems, avoid common IT problems, and solve issues when they occur.

Arlington Plastics Machinery

Arlington Plastics Machinery buys and sells new and used plastics machinery, providing auction, appraisal, marketing and exhibition services in the reseller market. More than five years ago, they realized they needed to invest in more effective and capable IT support – that’s why they came to Outsource IT Solutions Group.

Itasca Community Library

Itasca Community Library, a vital resource for its local community, first engaged Outsource Solutions Group (OSG) with immediate security concerns that required urgent remediation.

Itasca Community Library & Outsource Solutions Group

Itasca Community Library, a vital resource for its local community, first engaged Outsource Solutions Group (OSG) with immediate security concerns that required urgent remediation. Recognizing the importance of safeguarding their IT infrastructure, the library engaged OSG to address vulnerabilities and strengthen their security posture. What began as a focused security effort evolved into a long-term partnership, with OSG now providing fully managed services and supporting numerous large-scale initiatives.

Let’s Pave & Outsource Solutions Group

OSG launched a highly collaborative onboarding program for Let’s Pave immediately after the company became a customer, creating a smooth transition from its previous managed service provider.

Outsource Your IT Help Desk to OSG

Choose an IT partner with wide-ranging helpdesk support capabilities.

Why Clients Outsource IT Help Desk Services in Chicago to OSG

23 Years

Providing customized support to our business clients

30+

Experts committed to resolving IT issues as quickly as possible

80+

Professional certifications to widen our knowledge base

Strong Commitment to the Highest Service Levels

We believe our clients should remain with our Chicago IT company because they want to, not because their contract forces them to.

Consequently, we make it as easy to leave as it is to come onboard. Clients enjoy a no-risk experience that includes:

We also complete daily, monthly and quarterly IT and satisfaction reviews. If there is a quality issue, we want to be the first to know so we can resolve it before it costs your business time, money or customer trust.

Helpdesk Services Designed for Small to Medium Size Businesses

At OSG, we provide simplified helpdesk support services that are suitable for businesses with as few as 10 seats and as many as 150 seats.

This also illustrates the scalability of our services, so you can feel confident about growing with us. If necessary, you can even reduce your service needs in light of changes in the market or your business.

Whether you just need a help desk to tackle day-to-day IT issues or you’re looking for complete managed IT services, let OSG be your reliable partner.

Comprehensive Onboarding Service

Worried about making the switch? Our experienced professionals have simplified the onboarding process, so you can upgrade to better help desk support faster and easier.

To ensure a seamless transition to new managed helpdesk services, we complete the following tasks:

Our Other IT Services in Chicago

• Managed IT Chicago

• IT Support in Chicago

• IT Consulting in Chicago

• IT Outsourcing in Chicago

• IT Network Support in Chicago

• IT Company in Chicago

• Cyber Security in Chicago

Chicago IT Helpdesk Services - Frequently Asked Questions

What’s The Difference Between an IT Helpdesk & IT Support?

An IT helpdesk focuses on providing immediate, short-term solutions to users facing technical problems, primarily through a ticketing system. It’s your go-to for quick fixes and troubleshooting.

IT support offers a wider range of services, including strategic IT planning and infrastructure management. Support technicians often handle more complex issues that require in-depth technical knowledge and planning.

Does the Outsource Solutions Group Helpdesk Provide Support For Apple Devices?

The Outsource Solutions Group helpdesk supports Apple devices, including Mac and iOS mobile devices.

Our team is skilled in managing various operating systems, making us a perfect fit for businesses using various technologies.

This broad capability enables us to provide a unified work experience for all employees.

What’s The Point of Having Both an IT Helpdesk & an IT Support Team?

Having both an IT helpdesk and an IT support team allows for efficient problem-solving without overlooking long-term IT goals.

The helpdesk quickly resolves immediate technical issues, freeing the IT support team to tackle more complex challenges and strategic planning.

This setup ensures that urgent needs and future improvements both receive specialized attention.

Is Your IT Helpdesk Just For Businesses?

Outsource Solution Group’s IT helpdesk is designed specifically for businesses.

We do not support personal devices unless they are part of a BYOD (Bring Your Own Device) policy and connect to a current client’s business network.

This approach allows us to deliver focused and effective support to businesses that rely on technology for their daily operations.

I Need Help Now, Where Can I Get It?

If you’re currently a client and require immediate assistance, reach out to us by calling our support line at (630) 236-6625 or by contacting us to open a support ticket.

If you’re not yet a client but wish to join our services, you can begin the onboarding process through our website or by calling us at (855) 288-0344.