Senior AI Software Engineer Jobs in Chicago, IL

Senior AI Software Engineer jobs in Chicago are concentrated in the Loop, River North, and the Fulton Market tech corridor, with strong demand across fintech, healthcare tech, and enterprise software. Employers hiring right now include Fitch, Lenovo, and CVS Health. See the openings below and apply to the ones that match your experience.

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Overview

Open roles18
Top employerFitch
Work type100% Hybrid
Top credentialBachelor's degree
Companies hiring10

Showing 4 of 18+ Senior AI Software Engineer jobs

Reliance IT, Inc
AI Software Engineer 1
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Reliance IT, Inc
Added 1d ago
AI Software Engineer 1
Reliance IT, Inc
Chicago, Illinois
AI (Artificial Intelligence)
Data Science
$80k - $100k/yr
Bachelor's degree

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Caterpillar
Lead Software Engineer, Gen AI
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Caterpillar
Added 1d ago
Lead Software Engineer, Gen AI
Caterpillar
Chicago, Illinois
Business Analysis
Data Analytics
Data Science
$128k - $209k/yr
10,000+

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Lenovo
Software Engineer, AI Wearables
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Lenovo
Added 2d ago
Software Engineer, AI Wearables
Lenovo
Chicago, Illinois
Cloud & DevOps
Cloud Engineering
Solutions Architecture
Technical Product & Program Management
$100k - $140k/yr
Hybrid
Bachelor of Science
10,000+

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Intelligent Medical Objects
Sr. Software Engineer - AI Platforms and Automation
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Intelligent Medical Objects
Added 6d ago
Sr. Software Engineer - AI Platforms and Automation
Intelligent Medical Objects
Chicago, Illinois
Customer Service & Support
Customer Support
Product Management
Technical Program Management
$140k - $200k/yr
AWS Certification
11-50

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Senior AI Software Engineer Job Market in Chicago

Who's Hiring

Fitch
Fitch3 open roles
Lenovo
Lenovo2 open roles
CVS Health
CVS Health2 open roles

Top Industries Hiring

  • Fintech
  • Banking & Financial Services
  • Investment & Asset Management
  • Consulting & Professional Services

Senior AI Software Engineer Jobs in Chicago: Frequently Asked Questions

How do I get a senior ai software engineer job in Chicago?

Chicago's strongest hiring comes from fintech firms in the Loop, health tech companies in the Medical District corridor, and enterprise software players anchored in River North and Fulton Market. Candidates with hands-on experience in large language models, MLOps, or production-scale AI systems stand out here. Networking through Chicago-area AI and machine learning meetups and targeting mid-to-large firms with dedicated AI product teams gives applicants a concrete edge in this market.

Which companies hire senior ai software engineers in Chicago?

Employers hiring senior ai software engineers in Chicago right now include Fitch, Lenovo, and CVS Health, based on current listings on Migrate Mate as of August 2026. Chicago's hiring mix tends to favor established enterprises, regional financial institutions, and growth-stage tech companies rather than early-stage startups, so roles often come with larger team structures and well-defined AI infrastructure.

Are there remote senior ai software engineer jobs in Chicago?

Yes, and senior ai software engineering is among the more remote-compatible roles given that the core work involves code, models, and data rather than physical presence. About 100% of senior ai software engineer openings tied to Chicago are remote or hybrid as of August 2026, reflecting broad employer flexibility in this discipline. Model development, experimentation, and code review are the functions most commonly done fully remote, while roles requiring close collaboration with data engineering or product teams tend to favor hybrid schedules.

How can I get a senior ai software engineer job in Chicago with little or no experience?

The most realistic entry path in Chicago is through a machine learning engineer or data scientist role at one of the city's mid-size fintech or health tech companies, where cross-functional AI work is common and internal movement into senior roles happens faster than at large enterprises. Targeting Chicago-based companies with active AI product roadmaps, contributing to open-source projects, and building a portfolio of deployed models gives candidates a tangible edge over those with coursework alone. Organizations like the University of Chicago's Polsky Center and Chicago tech accelerators also connect early-career engineers with AI-focused employers in the region.

Which industries hire the most senior ai software engineers in Chicago?

Chicago senior ai software engineer roles concentrate in Fintech, Banking & Financial Services, and Investment & Asset Management, based on current listings on Migrate Mate as of August 2026. Chicago's deep roots in financial trading, insurance, and hospital systems create consistent institutional demand for AI talent that solves high-stakes prediction, risk modeling, and clinical decision-support problems.

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