Top penetration testing services in Chicago [July 2025]

In today’s evolving cybersecurity landscape, organizations of all sizes must proactively test their defenses to protect against data breaches, ransomware attacks, and compliance failures. For businesses operating in Chicago, a city known for its financial, healthcare, and tech industries, finding the right penetration testing partner is a vital step in staying secure.

This comprehensive guide explores the top penetration testing companies in Chicago, covering their specialties, engagement models, and feature capabilities. Whether you’re a startup in Fulton Market or a well-established enterprise in the Loop, this blog will help you make an informed decision.

Why penetration testing matters more than ever

Penetration testing, or pentesting, simulates real-world cyberattacks to identify vulnerabilities before malicious actors can exploit them. While vulnerability scanning tools offer some coverage, they often fail to simulate how an attacker might chain exploits to breach your systems.

With the rise in cloud-native applications, API-first development, and compliance requirements like PCI-DSS, HIPAA, and ISO 27001, proactive testing has become a boardroom concern.

Choosing the right vendor in Chicago means finding a partner who can address your security needs with accuracy, speed, and transparency.

What to look for in a pentesting service

Before diving into the list of top companies, here are some key factors to evaluate:

• Engagement model: Manual, automated, or hybrid?

• Speed & frequency: Point-in-time vs continuous pentesting

• Reporting quality: Technical findings + business impact

• Integration capabilities: CI/CD compatibility, developer workflows

• Compliance alignment: SOC 2, ISO 27001, PDPA, HIPAA readiness

• Cost & scalability: Can it grow with your security program?

Top penetration testing companies in Chicago

1. Infiniwiz

Infiniwiz provides cybersecurity services with a strong focus on network infrastructure, endpoint security, and managed IT. Their manual pentesting offering is tailored to smaller businesses in sectors like healthcare and finance.

• Engagement model: Manual

• Ideal for: SMEs, healthcare, financial firms

• Key features:

• Manual pentesting
• Automated pentesting
• CI/CD integration
• API security testing
• Complex authentication bypass
• Compliance friendly reports

2. Redpoint cybersecurity

Redpoint specializes in incident response, red teaming, and threat detection. Their penetration testing services are suited for government entities and large enterprises requiring post-breach simulation.

• Engagement model: Manual

• Ideal for: Large enterprises, government entities

• Key features:

• Manual pentesting
• Automated pentesting
• CI/CD integration
• API security testing
• Complex authentication bypass
• Compliance friendly reports

3. Halock

A respected name in the Midwest, Halock takes a risk-based approach to penetration testing. They emphasize governance, risk management, and compliance alongside their technical assessments.

• Engagement model: Manual

• Ideal for: Mid to large enterprises, highly regulated industries

• Key features:

• Manual pentesting
• Automated pentesting
• CI/CD integration
• API security testing
• Complex authentication bypass
• Compliance friendly reports

4. Xervant CyberSecurity

Xervant blends cloud security and application testing with DevSecOps practices. Their hybrid pentesting approach makes them a good fit for startups and digital-native teams.

• Engagement model: Manual + Hybrid

• Ideal for: Digital-first companies, startups

• Key features:

• Manual pentesting
• Automated pentesting
• CI/CD integration
• API security testing
• Complex authentication bypass
• Compliance friendly reports

5. InfoSight

With a legacy in threat intelligence and managed detection, InfoSight delivers risk-based penetration testing tailored to the needs of banks, insurers, and medical facilities.

• Engagement model: Manual

• Ideal for: Banking, healthcare, insurance

• Key features:

• Manual pentesting
• Automated pentesting
• CI/CD integration
• API security testing
• Complex authentication bypass
• Compliance friendly reports

6. Defend Edge

Defend Edge delivers advanced security operations, red teaming, and attack simulations. Their manual testing services are often used by government contractors and large enterprises.

• Engagement model: Manual

• Ideal for: Government agencies, large enterprises

• Key features:

• Manual pentesting
• Automated pentesting
• CI/CD integration
• API security testing
• Complex authentication bypass
• Compliance friendly reports

Comparing engagement models

Penetration testing isn’t one-size-fits-all. Here’s a look at how the different engagement models stack up:

Automated pentesting tools offer faster turnaround and lower costs, making them ideal for CI/CD pipelines. Manual testing, while slower, is great for deep assessments and compliance. Hybrid models offer the best of both worlds.

Why it matters to get this right

Chicago’s businesses are undergoing rapid digital transformation. Whether you’re building a SaaS product, securing sensitive healthcare data, or defending critical infrastructure, your security practices must evolve in parallel.

The right penetration testing partner can help you:

• Discover hidden vulnerabilities

• Meet compliance mandates

• Protect customer trust

• Reduce risk from third-party integrations

Investing in quality pentesting is about building resilience into the fabric of your tech stack.

Beagle Security: An alternative for teams that move fast

If you’re looking for something that goes beyond traditional manual pentesting, Beagle Security is worth a closer look. As an AI-powered automated pentesting platform, Beagle helps modern development teams:

• Continuously test applications

• Catch vulnerabilities during deployment

• Get compliance-ready reports in minutes

• Integrate seamlessly with CI/CD pipelines

Beagle combines speed, accuracy, and developer-friendliness. This makes it a great fit for both fast-moving startups and compliance-heavy enterprises.

Whether you need quick turnarounds or deep hybrid assessments, Beagle Security’s flexible plans and API security testing capabilities can scale with your team.

Start a 14-day free trial or schedule a call to get started with the Beagle Security platform.

Written by

Febna V M

Cyber Security Engineer

Contributor

Nandagopal S

Marketing Associate