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118 leave jobs at 76 companies in Chicago, IL

1mo
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Leave & Benefits Specialist
Chicago or Dallas or Milwaukee
$78k-$119k/yr HybridFull Time
Foley & Lardner
Foley & Lardner: International law firm providing legal and business counsel.
3+ YOEBachelor's degree and minimum 3 years administering health and welfare benefits and leave programs (FMLA, STD); HRIS experience preferred; strong compliance and case management skills.
HRIS
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1mo
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Leave & Employee Relations Senior Consultant
Chicago, Illinois, United States
$72k-$141k/yr HybridFull Time
CNA
CNANYSE: CNA: Provides commercial property and casualty insurance and risk management.
5+ YOE5+ years leave administration/employee relations experience; deep knowledge of FMLA, ADA, USERRA, leave programs; experience handling complex leave and accommodation cases; bachelor’s degree or equivalent experience.
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3w
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Leave Specialist – Hybrid Chicago Loop Office
Chicago, Illinois, United States
$72k-$85k/yr HybridFull Time
NORC at the University of Chicago
NORC at the University of Chicago: Conducts objective social science research and public policy analysis.
3+ YOEBachelor's degree or equivalent; 3+ years leave/benefits/absence management experience; knowledge of FMLA, ADA, USERRA, HIPAA, COBRA, workers' compensation; strong case management and communication skills.
Human Resource Information Systems (HRIS), Microsoft Office, Microsoft Excel
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Benefits and Leave Specialist
Chicago, Illinois, United States
$75k-$90k/yr OnsiteFull Time
NOCD
NOCD: Telehealth platform for specialized obsessive-compulsive disorder treatment.
4+ YOE4+ years benefits/leave administration experience; knowledge of FMLA, ADA, COBRA, ACA, HIPAA; HRIS and benefits billing reconciliation experience; strong organization and communication skills.
Google Suite, Slack, Lattice
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1mo
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Leave and Accommodation Specialist
Hoffman Estates, Illinois, United States
$55k-$77k/yr OnsiteFull Time
Crystal Clean
Crystal Clean: Provides environmental waste management and industrial cleaning services.
3+ YOEBachelor's degree in HR or related field, 3+ years leave/accommodation/workers' comp experience, strong knowledge of FMLA/ADA/workers' comp, HRIS proficiency, confidentiality and communication skills.
HRIS, leave management systems
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1w
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Leave and Accommodations Business Partner
Chicago, Illinois, United States
$90k-$92k/yr OnsiteFull Time
United Ground Express
United Ground ExpressNASDAQ: UAL: Providing ground handling and passenger services for airlines.
5+ YOEBachelor's degree,5+ years HR experience with leave/accommodation administration,deep knowledge of FMLA/ADA/state leave laws,experience centralizing HR functions,proficiency with HRIS and Microsoft Office.
HRIS, Microsoft Office
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3mo
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Leave Administration and Accommodations Manager
Chicago, Illinois, United States
$107k-$147k/yr HybridFull Time
Sidley Austin
Sidley Austin: Global law firm providing comprehensive legal and regulatory counsel.
5+ YOEBachelor's or equivalent, 5+ years managing multi-state leave and accommodation programs, strong knowledge of FMLA/CFRA/ADA/ADAA/PWFA, vendor management, HRIS and reporting, excellent communication and analytical skills.
Workday, AbsenceSoft
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2mo
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Leave of Absence Coordinator
Chicago, Illinois, United States
$19/hr HybridFull Time
Sedgwick
Sedgwick: Provides global insurance claims management and risk services.
High school diploma or GED; strong communication; computer literacy; clerical or customer service experience preferred.
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3w
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Teacher Assistant (Leave of Absence)
Crete, Illinois, United States
$150/day OnsiteTemporary
Crete-Monee School District 201-U
Crete-Monee School District 201-U: Provides public K-12 education to the Crete-Monee community.
Support classroom teacher during a leave-of-absence long-term assignment; assist with student supervision and instructional activities. Daily pay stated.
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3w
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Teacher -Science (Leave Of Absence)
Gurnee, Illinois, United States
OnsiteFull Time
Chicago Education Project
Chicago Education Project: Private non-profit school for students with autism and disabilities.
Must hold Illinois Professional Educator License or Substitute License and be registered in Lake County ROE 34; available for leave dates 8/10/2026-9/25/2026.
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4w
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Teacher of Students with Disabilities - Leave Replacement
Hanover Park, Illinois, United States
$62k-$116k/yr OnsiteFull Time, Temporary
Hanover Park Regional High School District
Hanover Park Regional High School District: Public high school district serving students in Morris County.
Leave-replacement high school special education teacher (Aug 31–on or about Nov 2, 2026). Position follows district salary guide and offers medical, prescription, and dental benefits.
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2w
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Specialized Services Administrative Assistant (Temporary Leave of Absence)
South Holland, Illinois, United States
OnsiteTemporary
South Holland School District 150
South Holland School District 150: Providing public elementary and middle school education services.
Provide administrative and clerical support for specialized services in the school district during a temporary leave starting 08/03/2026.
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4w
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Hygienist Leave of Absence
Bloomingdale, Illinois, United States
OnsiteFull Time, Temporary
J & J Dental Support Services
J & J Dental Support Services: Provides operational and administrative support to multi-location dental practices.
Active Illinois dental hygienist license and current CPR; ability to provide preventive and periodontal care, take radiographs, communicate effectively, and work independently in a clinical team.
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2w
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English Teacher (Maternity Leave)
Oak Forest, Illinois, United States
OnsiteFull Time, Temporary
Bremen High School District 228
Bremen High School District 228: Operates four public high schools in suburban Chicago.
Valid Illinois Type 09 certification with English/Language Arts endorsement (Drama or Journalism acceptable); ability to plan instruction, assess learning, manage classroom behavior, communicate with families, and grow professionally.
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2d
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Leave Management Ability Analyst
United States or Hartford or San Antonio or Lake Mary or Sunrise or Scottsdale or Alpharetta or Naperville
$52k-$69k/yr HybridFull Time
The Hartford
The HartfordNYSE: HIG: Provides property and casualty insurance and financial products.
High school diploma or GED required; associate or bachelor's degree preferred. Claim experience, medical terminology, Microsoft Office proficiency, critical thinking, communication, organization, and problem-solving skills are valued.
Microsoft Office
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3d
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Leave Management Ability Analyst
United States or Hartford or San Antonio or Lake Mary or Sunrise or Scottsdale or Alpharetta or Naperville
$52k-$69k/yr HybridFull Time
The Hartford
The HartfordNYSE: HIG: Provides business and personal insurance, group benefits, and investments.
High school diploma or GED required; associate or bachelor's degree preferred. Requires strong organization, problem-solving, critical thinking, communication, accuracy, and Microsoft Office proficiency.
Microsoft Office
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1mo
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Leave Coverage: School Social Worker at Cumberland Elementary School
Des Plaines, Illinois, United States
OnsiteTemporary
Community Consolidated School District 62
Community Consolidated School District 62: Public school district serving K-8 students in Des Plaines.
Leave coverage (Aug 20–Nov 9, 2026) for a school social worker at Cumberland Elementary. Requires a current valid Illinois Professional Educator License with appropriate endorsement; middle school experience preferred.
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1w
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Temporary School Counselor (MAT Leave)
Chicago, Illinois, United States
$64k-$83k/yr OnsiteTemporary, Full Time
Chicago Public Schools
Chicago Public Schools: Public school district providing K-12 education in Chicago.
Master's degree in school counseling and current Illinois Professional Educator License with School Counseling Endorsement required.
Naviance
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1w
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Maternity Leave Math/Science Teacher
Chicago, Illinois, United States
OnsiteFull Time, Temporary
Intrinsic Schools
Intrinsic Schools: Operates innovative public charter schools in Chicago.
Plan and deliver rigorous secondary math and science instruction, analyze student data, personalize learning with technology, mentor students, collaborate with support teams, and communicate with families.
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1w
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Temporary School Counselor (MAT Leave)
Chicago, Illinois, United States
OnsiteTemporary
Chicago Public Schools
Chicago Public Schools: Public school district serving the city of Chicago.
Master's degree in school counseling and current Illinois Professional Educator License with School Counseling Endorsement; provides comprehensive academic, personal/social, and career counseling.
Naviance
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