Our Chicago cloud methodology combines migration planning, security architecture, and cost optimisation. Assessment: cloud readiness and migration planning. Cloud assessment: evaluating each workload for cloud suitability — not assuming everything should migrate. Assessment dimensions: technical fit (can this workload run effectively in cloud? Latency requirements, data gravity, hardware dependencies, and licensing constraints), business case (will cloud actually save money for this workload? Comparing current on-premises cost with projected cloud cost — including the migration investment), compliance fit (can this workload meet compliance requirements in cloud? HIPAA, PCI, CFTC data retention, and industry-specific regulations), and risk assessment (what are the risks of migration? Data loss, downtime, performance degradation, and dependency on cloud provider). Migration strategy: for each workload, determining the appropriate migration approach — rehost (lift-and-shift — moving to cloud without code changes. Fastest migration but least cloud-optimised), replatform (minor adjustments for cloud — moving to managed database services, containerising applications, or adjusting for cloud networking), refactor (significant rearchitecture — decomposing monoliths, implementing cloud-native patterns, and leveraging managed services. Most cloud benefit but highest investment), and retain (keeping on-premises — workloads where cloud migration doesn't make technical or economic sense). Security: cloud security architecture. Cloud security for Chicago regulated environments: identity and access management (least-privilege IAM policies, MFA for all human access, service accounts with minimal permissions, and automated credential rotation), network security (VPC architecture with proper segmentation, private subnets for sensitive workloads, VPN/Direct Connect for hybrid connectivity, and WAF for internet-facing applications), data protection (encryption at rest using KMS-managed keys, encryption in transit using TLS, and data classification driving protection controls), compliance controls (HIPAA: BAA, PHI encryption, access logging, and minimum necessary data access. Financial: data retention, audit trails, and regulatory reporting data availability. SOC 2: security controls mapped to SOC 2 Trust Services Criteria), and monitoring (CloudTrail/Azure Monitor/GCP Audit Logs for activity monitoring, Security Hub/Defender for Cloud for posture management, and SIEM integration for security event correlation). Cost optimisation: cloud FinOps. Cost management: preventing the cloud cost surprises that plague many Chicago enterprise migrations — right-sizing (analysing actual resource utilisation and recommending appropriate instance sizes — most initial migrations over-provisioned by 40-60%), reserved capacity (committed-use discounts for predictable workloads — 1-year or 3-year reservations reducing compute costs 30-60%), auto-scaling (scaling resources based on actual demand — reducing costs during off-peak hours while ensuring capacity during peak), storage tiering (data lifecycle policies moving infrequently accessed data to cheaper storage tiers — S3 Intelligent-Tiering, Azure Cool/Archive), and ongoing FinOps (monthly cost review identifying waste, optimising reservations, and recommending architectural changes to reduce costs. The discipline: treating cloud cost management as an ongoing practice, not a one-time exercise).