Compliance Specialist Jobs in Chicago, IL
Compliance specialist jobs in Chicago are in strong demand, concentrated in the Loop, Streeterville, and River North across financial services, healthcare, and manufacturing. Employers hiring right now include 5T Management, OFI, and GATX. Scan the live roles below and apply to whichever ones fit.
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Who We Are:
When you join Traffic Tech, you join a team that keeps the global economy moving – literally.
Traffic Tech is recognized as an industry leader and the logistics partner to many highly recognizable international brands. With 30 offices throughout the United States, Canada, Mexico and China, the company offers progressive & efficient solutions for moving freight by land, sea, and air.
Your Part in It:
Working out of our Chicago office, we are looking for our next Senior Technical Specialist – U.S. Customs Compliance & Duty Recovery. In this role, you will serve as a technical resource on complex U.S. Customs matters, helping ensure compliance, identify duty-saving opportunities, and support clients with customs and duty recovery initiatives. You will work closely with internal teams and clients to review customs entries, provide technical guidance, and develop effective compliance and recovery strategies.
SENIOR TECHNICAL SPECIALIST - U.S. CUSTOMS COMPLIANCE AND DUTY RECOVERT
What the Job Entails:
- Serve as a technical resource on complex U.S. Customs matters, including classification, valuation, country of origin, free trade agreements, special tariffs, and other import compliance requirements.
- Perform quality-control reviews of customs entries and supporting documentation to identify potential errors, compliance risks, and duty-saving opportunities.
- Review entry data and filing practices to ensure accuracy and compliance with U.S. Customs and Border Protection requirements.
- Lead and support duty recovery initiatives, including Post Summary Corrections (PSCs), protests, refunds, drawback, and other available recovery mechanisms.
- Identify opportunities to reduce duty exposure and recover overpaid duties for clients through detailed entry and historical data reviews.
- Provide technical guidance to customs specialists, entry writers, account managers, and clients on complex customs matters.
- Research U.S. Customs regulations, rulings, tariff changes, trade remedies, and regulatory developments, and communicate their impact internally and to clients.
- Support clients with customs audits, CBP inquiries, requests for information, classification reviews, valuation matters, and other technical compliance issues.
- Assist with the development and maintenance of customs compliance procedures, technical guidance, and quality-control standards.
- Work directly with clients to provide consultative support and develop customs strategies related to compliance, duty mitigation, and recovery opportunities.
What We Are Looking For:
- Minimum 5 years of experience in U.S. Customs brokerage, trade compliance, customs consulting, or a similar technical customs role.
- Strong technical knowledge of U.S. import regulations and CBP requirements.
- Strong understanding of HTS classification, customs valuation, country of origin, USMCA and other free trade agreements, and special duty programs.
- Experience reviewing customs entries for accuracy, compliance, and duty-saving opportunities.
- Experience with Post Summary Corrections, protests, duty refunds, and other post-entry correction or recovery programs.
- Experience with drawback programs is a strong advantage.
- Mandatory hands-on experience with CargoWise.
- Strong research, analytical, and problem-solving skills with the ability to interpret customs regulations and rulings.
- Excellent verbal and written communication skills with the ability to explain complex customs matters clearly to clients and internal teams.
- Licensed U.S. Customs Broker designation is an asset.
What We Offer:
- Robust industry with training and mentorship
- Full Benefit options, including Medical (Dental & Vision)
- Life/AD&D Insurance, Long-term Disability
- 401(k) matching
- Dynamic environment and ‘can-do’ culture
This is a full-time permanent position from Monday to Friday.
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Who's Hiring



Top Industries Hiring
- Education
- Manufacturing
- Food & Beverage
Compliance Specialist Jobs in Chicago: Frequently Asked Questions
How do I get a compliance specialist job in Chicago?
Target Chicago's dense financial services corridor in the Loop and River North, where banks, trading firms, and insurance companies post the most openings. Healthcare systems anchored in Streeterville and the Medical District also hire heavily. Candidates who combine regulatory knowledge with industry-specific experience, whether in financial regulations, HIPAA, or environmental compliance for manufacturing, stand out in this market.
Which companies hire compliance specialists in Chicago?
Chicago compliance specialist roles are posted by 5T Management, OFI, and GATX and others right now, based on current listings on Migrate Mate as of September 2026. Chicago's employer mix skews toward large financial institutions, regional banks, major hospital networks, and industrial manufacturers with significant regulatory footprints.
Are there remote compliance specialist jobs in Chicago?
Yes, though remote availability varies: analytical and policy-focused compliance roles tend to go remote more readily than positions requiring on-site audits or in-person regulatory meetings. About 63% of compliance specialist openings tied to Chicago are remote or hybrid as of September 2026, with hybrid arrangements most common at large Loop-based financial firms.
How can I get a compliance specialist job in Chicago with little or no experience?
The most realistic entry path in Chicago is through compliance coordinator or analyst roles at regional banks, insurance carriers, or large healthcare systems, which regularly hire candidates with a relevant bachelor's degree and strong attention to detail. Roles in Know Your Customer review, claims audit, or quality assurance at Chicago-area firms also serve as common lateral entry points into full compliance careers.
Which industries hire the most compliance specialists in Chicago?
Chicago compliance specialist roles concentrate in Education, Manufacturing, and Food & Beverage, based on current listings on Migrate Mate as of September 2026. Chicago's role as a global financial hub and home to major healthcare networks and industrial manufacturers makes it one of the densest compliance job markets in the Midwest.
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