Penetration Testing Services in Chicago
Penetration testing Chicago providers delivering multi-scope engagements across web, mobile, cloud, API, network, and infra, mapped to CVSS v4.0, OWASP Top 10, and CWE/SANS Top 25 with compliance-ready reports and seamless CI-CD and workflow integrations.
Top pentesting vendors in Chicago.
Astra Security
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Astra Security is a CREST-approved and PCI ASV-certified penetration testing company dedicated to securing websites and businesses online. Our comprehensive VAPT services cover a broad spectrum of digital assets, including websites, applications, cloud infrastructure, network devices, and emerging technologies like blockchain.
Redpoint Cybersecurity
Redpoint Cybersecurity is a Chicago-headquartered testing company that focuses on identifying and mitigating security risks. They offer penetration testing, threat hunting, ethical hacking and vulnerability assessments.
Xervant Cyber Security
Xervant Cyber Security is a cybersecurity firm specializing in penetration testing and network security assessments to help organizations identify and mitigate potential vulnerabilities within their network infrastructure. Xervant’s penetration testing services are conducted by certified information security professionals who utilize a combination of industry-standard and proprietary tools, along with manual inspections by experienced InfoSec experts.
InfoSight
InfoSight, Inc. is a Chicago-based cybersecurity and risk management firm, that offers advanced security solutions, including penetration testing, to protect clients across the nation from cyber threats.
Infiniwiz
Infiniwiz is IT Support & Managed IT Services company in Chicago that offers engineering, systems integration, penetration testing and risk assessment for businesses. They specialize in software architecture, development, and security risk analysis.
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Navigating Chicago’s compliance landscape? Secure your systems with Astra’s audit-ready penetration testing.
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The clear winner
Why Chicago-based companies choose Astra Security
Astra puts your ahead by finding and fixing every single security loopholde
with our hacker-style pentest.
AI-Powered Intelligence
- Run 15,000+ tailored AI test scenarios to your unique app
- Contextual remediation advice at your fingertips
- Continuously improves detection accuracy through context-aware analysis and evolving ML models trained on real-world vulnerability patterns.
Compliance-First Approach
- Audit-ready reports aligned with ISO, PCI, SOC 2, HIPAA, GDPR, OWASP, NIST, and more.
- Expert support to simplify assessments and pass audits faster.
DevOps Integration
- Integrate into CI/CD with GitHub Actions, GitLab CI, Jenkins, Bitbucket, and more.
- Automate scans, send vulnerability alerts via Slack
- Create JIRA tickets, all without leaving your pipeline.
End-to-End, Fully Managed Platform
- Continuous, scheduled scans and pentests for web apps, API, and cloud without manual setup or tuning.
- Expert-tuned accuracy with optimized scanners to reduce false positives.
- Vulnerabilities triaged and mapped to real business impact.
- Auto-generated compliance-grade summaries with remediation guidance and automated rescans for verification.
Pentest Certificate & AI-built Trust Center
- Publicly verifiable certifications with shareable links.
- Demonstrate your security commitment.
- Build client and partner trust.
- Summarize your security posture for easy sharing with customers and auditors
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Loved by 1000+ CTOs & CISOs worldwide
We are impressed by Astra's commitment to continuous rather than sporadic testing.
Astra not only uncovers vulnerabilities proactively but has helped us move from DevOps to DevSecOps
Their website was user-friendly & their continuous vulnerability scans were a pivotal factor in our choice to partner with them.
The combination of pentesting for SOC 2 & automated scanning that integrates into our CI pipelines is a game-changer.
I like the autonomy of running and re-running tests after fixes. Astra ensures we never deploy vulnerabilities to production.
We are impressed with Astra's dashboard and its amazing ‘automated and scheduled‘ scanning capabilities. Integrating these scans into our CI/CD pipeline was a breeze and saved us a lot of time.
We are impressed by Astra's commitment to continuous rather than sporadic testing.
Astra not only uncovers vulnerabilities proactively but has helped us move from DevOps to DevSecOps
Their website was user-friendly & their continuous vulnerability scans were a pivotal factor in our choice to partner with them.
The combination of pentesting for SOC 2 & automated scanning that integrates into our CI pipelines is a game-changer.
I like the autonomy of running and re-running tests after fixes. Astra ensures we never deploy vulnerabilities to production.
We are impressed with Astra's dashboard and its amazing ‘automated and scheduled‘ scanning capabilities. Integrating these scans into our CI/CD pipeline was a breeze and saved us a lot of time.
Frequently asked questions
Penetration testing in Chicago generally costs between $5,000 and $50,000, depending on business size, scope, complexity, and compliance needs. Highly regulated sectors or large-scale infrastructures may incur higher costs for more comprehensive assessments.
Select Chicago-based penetration testing firms with strong industry credentials, client references, and recognized certifications like OSCP, CREST, or ISO 27001. Assess their methodology, reporting quality, and experience with relevant US regulations and local industry requirements.
Penetration testing is essential for Chicago businesses to detect vulnerabilities, prevent data breaches, and comply with regulations like PCI DSS, HIPAA, and local privacy laws. It also enhances customer trust and strengthens overall cybersecurity posture.
Chicago companies should conduct penetration testing annually or after major system updates. Highly regulated sectors, such as healthcare and finance, may require more frequent testing to ensure ongoing compliance and heightened protection against evolving threats.
While not always explicitly required, penetration testing is recommended under frameworks like PCI DSS, HIPAA, and the NIST CSF. It helps demonstrate due diligence for compliance with both federal and local cybersecurity expectations.
Penetration testing assists Chicago organizations in identifying, documenting, and remediating security gaps. It is critical for meeting regulatory requirements, passing audits, and maintaining compliance with standards such as PCI DSS, HIPAA, and ISO 27001.
Yes, remote penetration testing is commonly available for Chicago businesses. Secure connectivity allows assessors to evaluate web apps, networks, and APIs thoroughly, providing accurate results without requiring on-site visits.
