27 leisure travel agent jobs found in Chicago

This is an opportunity to join Ascot Group - one of the world’s preeminent specialty risk underwriting organizations. Designed as a modern-era company operating through an ecosystem of interconnected global operating platforms, we’re bound by a common mission and purpose: One Ascot. Our greatest strength is a talented team who flourish in a collaborative, inclusive, and entrepreneurial culture, steeped in underwriting excellence, integrity, and a passion to find a better way, The Ascot Way. The Ascot Way guides our people and our organization. Our underwriting platforms collaborate to find creative ways to deploy our capital in a true cross-product and cross-platform approach. These platforms work as one, deploying our capital creatively through our unique Fusion Model: Client Centric, Risk Centric, Technology Centric. Built to be resilient, Ascot maximizes client financial security while delivering bespoke products and world class service — both pre- and post-claims....

This is an opportunity to join Ascot Group - one of the world’s preeminent specialty risk underwriting organizations. Designed as a modern-era company operating through an ecosystem of interconnected global operating platforms, we’re bound by a common mission and purpose: One Ascot. Our greatest strength is a talented team who flourish in a collaborative, inclusive, and entrepreneurial culture, steeped in underwriting excellence, integrity, and a passion to find a better way, The Ascot Way. The Ascot Way guides our people and our organization. Our underwriting platforms collaborate to find creative ways to deploy our capital in a true cross-product and cross-platform approach. These platforms work as one, deploying our capital creatively through our unique Fusion Model: Client Centric, Risk Centric, Technology Centric. Built to be resilient, Ascot maximizes client financial security while delivering bespoke products and world class service — both pre- and post-claims....

Company Shared Services Argo and Farm Family are specialty property and casualty insurance brands whose underwriting companies are wholly-owned subsidaries of Clearbrook Holdings Inc. Argo and Farm Family partner with agents and brokers to provide insurance solutions that enable businesses to manage risks with confidence. Job Description The VP, Ceded Reinsurance leads the end-to-end execution of outwards treaty reinsurance placements for Clearbrook Group Holdings, Inc. across all property and casualty lines.  This role is a strategic partner to the business, supporting the unique needs of Argo Casualty, Argo Specialty, Farm Family, and Runoff segments. You will be responsible for structuring complex reinsurance programs, managing global broker and reinsurer relationships, and ensuring the group’s capital and balance sheet interests are protected through robust risk transfer strategies.  Placement Strategy + Execution End-to-end placement: lead the lifecycle of...

Job Description Are you looking for your next opportunity? Sompo has a unique opportunity for an Assistant Vice President in our E&S Property team. Our E&S Property team considers all types of commercial occupancies for catastrophe protection based on individual risk characteristics. We entertain single location risks as well as large schedules of locations and consider risks throughout the US including those located in both catastrophe prone and non-catastrophe prone areas. Location: This position will be based out of our Chicago, IL; New York, NY; Morristown, NJ, Garden City, NY, Purchase, NY and Boston, MA areas. We strive for collaboration, which is why we offer a work environment where our employees thrive and develop long-lasting careers. Our business, your impact, our opportunity: What you’ll be doing: Effectively drive acceptable submission activity and quickly determine acceptability of risk in accordance with...

Description Liberty Mutual Insurance is a leading global insurer committed to helping people live safer, more secure lives. Within our Personal Lines business, we partner with independent agents across the United States to deliver a broad portfolio of property and casualty solutions. We value a diverse, inclusive workforce and offer meaningful work where your expertise directly impacts growth, customer experience, and the communities we serve.   As a Senior Territory Manager, you will drive profitable premium growth across an assigned territory by building strong, consultative partnerships with independent agents. This role is critical to expanding market share through strategic agency management, collaboration with underwriting and internal partners, and disciplined execution of Personal Lines growth initiatives.   Key Responsibilities   Own and manage an assigned territory, driving profitable growth in alignment with financial and operational...

Posting Title: Investment Operations Analyst/Associate Location: Chicago, IL (Mostly On-Site) Employment Type: Full-time About Us: EquiTrust Life Insurance Company is a national carrier of competitive, client-friendly annuity products sold through a variety of distribution channels, including more than 20,000 independent agents and independent marketing organizations (IMOs). Since 2003, we have provided exceptional customer service to our clients by operating with integrity and passion. Our efforts are supported by a dedicated workforce who execute their responsibilities through teamwork and an entrepreneurial spirit. EquiTrust sells products nationwide and is headquartered in Chicago, Illinois, with operations in West Des Moines, Iowa. How You’ll Contribute: As an Investment Operations Analyst or Associate, you will play a key role in supporting the day-to-day operations of our investment portfolio. This includes trade processing, reconciliation, and maintaining...

MSIG USA continues to grow!  Company Overview: MSIG USA is the US-based subsidiary of  MS&AD Insurance Group Holdings, Inc. , one of the world’s top P&C carriers and a global Class 15 insurer, with A+ ratings and a reach that spans 40+ countries and regions. Leveraging our 350-year heritage, MSIG USA brings the financial strength, expertise, and global footprint to offer commercial insurance solutions that address your business’s unique risks. The Cargo/Ocean Marine Underwriter plays a critical role in evaluating, pricing, and managing risks associated with domestic and international cargo shipments. This position supports profitable growth of the marine portfolio by applying sound underwriting judgment, building strong broker relationships, and staying ahead of global trade and logistics trends. Key Responsibilities Underwriting & Risk...

Company Argo Group Argo Group is an underwriter of specialty insurance products in the property and casualty market. Argo offers a full line of products and services designed to meet the unique coverage and claims-handling needs of businesses. The Argo entities are wholly-owned subsidiaries of Clearbrook Group Holdings Inc. Job Description Argo / Farm Family currently has a challenging opportunity for an Account Manager in their Excess Casualty line of business.  This position will provide support and assistance to the overall underwriting function through customer service, processing of various underwriting transactions, data research, and analysis.  The Account Manager plays a pivotal role in delivering customer service excellence to our internal and external partners. This role will work onsite daily from our Chicago, Los Angeles, or New York City office location . The primary duties and responsibilities of the role are: Analyze and process account...

Job Description ABOUT US At HUB International, we are a team of entrepreneurs. We believe in protecting and supporting the aspirations of individuals, families, and businesses. We help our clients evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees to learn, grow, and make a difference. Our structure enables our teams to maintain their own unique, regional culture while leveraging support and resources from our corporate centers of excellence. HUB is a global insurance and employee benefits broker, providing a boundaryless array of business insurance, employee benefits, risk services, personal insurance, retirement, and private wealth management products and services. With over $5 billion in revenue and almost 20,000 employees in 600 offices throughout North America, HUB has grown substantially, in part due to our industry leading success in mergers and acquisitions About the Job We are seeking...

What part will you play? If you’re looking for a place where you can make a meaningful difference, you’ve found it. The work we do at Markel gives people the confidence to move forward and seize opportunities, and you’ll find your fit amongst our global community of optimists and problem-solvers. We’re always pushing each other to go further because we believe that when we realize our potential, we can help others reach theirs. Join us and play your part in something special! The primary purpose of this position is to underwrite new business and renewals in a profitable manner and according to authority level and established guidelines, and drive projects having an impact on the business. Assigned larger, more important and more complex accounts. Utilize underwriting tools to determine accurate classifications, rates, and premium charges. Understand state laws, including cancellation and non-renewal, within assigned territory to properly transact business within each state....

ABOUT US At HUB International, we are a team of entrepreneurs. We believe in protecting and supporting the aspirations of individuals, families, and businesses. We help our clients evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees to learn, grow, and make a difference. Our structure enables our teams to maintain their own unique, regional culture while leveraging support and resources from our corporate centers of excellence. HUB is a global insurance and employee benefits broker, providing a boundaryless array of business insurance, employee benefits, risk services, personal insurance, retirement, and private wealth management products and services. With over $5 billion in revenue and almost 20,000 employees in 600 offices throughout North America, HUB has grown substantially, in part due to our industry leading success in mergers and acquisitions The Opportunity   Today, the rapid advancement of...

Company Details   About Berkley One Berkley One is a modern insurance provider for a modern generation of affluence. We serve clients who live dynamic, adventurous lives and expect their insurance experience to match. Our mission is to deliver highly personalized risk and claims management through a blend of expert independent agents, cutting-edge digital tools, and the strength of the Berkley brand.   Why Join Us? At Berkley One, you’ll be part of a forward-thinking team that’s reimagining personal insurance. We’re building solutions that are as sophisticated and agile as the clients we serve—individuals and families who value innovation, simplicity, and exceptional service. You’ll collaborate with passionate professionals, leverage modern technology, and help shape the future of our industry.   What We Value A client-first mindset with a passion for delivering exceptional experiences Curiosity, creativity, and a drive to challenge...

What part will you play? If you’re looking for a place where you can make a meaningful difference, you’ve found it. The work we do at Markel gives people the confidence to move forward and seize opportunities, and you’ll find your fit amongst our global community of optimists and problem-solvers. We’re always pushing each other to go further because we believe that when we realize our potential, we can help others reach theirs. Join us and play your part in something special! The primary purpose of this position is to underwrite new business and renewals in a profitable manner and according to authority level and established guidelines, and drive projects having an impact on the business. Assigned larger, more important and more complex accounts. Utilize underwriting tools to determine accurate classifications, rates, and premium charges. Understand state laws, including cancellation and non-renewal, within assigned territory to properly transact business within each state....

You have a clear vision of where your career can go. And we have the leadership to help you get there.  At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential.  Individual contributor providing the highest level of technical leadership in the design, development, and scaling of CNA's AI-native agentic engineering platform. This role operates at the intersection of AI systems engineering, developer experience, and software delivery — building the foundational platform capabilities that enable the broad engineering organization to build, ship, and run high-quality, secure AI-native systems at the speed of AI. The focus is on designing and delivering agentic workflows, AI-augmented CI/CD pipelines, reusable skills and agent frameworks, and quality/security guardrails that make AI-accelerated delivery safe and scalable across the enterprise. JOB...

What part will you play? If you’re looking for a place where you can make a meaningful difference, you’ve found it. The work we do at Markel gives people the confidence to move forward and seize opportunities, and you’ll find your fit amongst our global community of optimists and problem-solvers. We’re always pushing each other to go further because we believe that when we realize our potential, we can help others reach theirs. Join us and play your part in something special! This position will be responsible for the resolution of low to moderate complexity and low to moderate exposure professional liability claims against lawyers and financial advisors. The position will have increased responsibility for decision making within their authority and work under general direction from their manager. Responsibilities: Investigate, negotiate and settle primary and excess policy professional liability claims against lawyers and financial advisors. Investigate and analyze...

Program Manager - Accident and Health Join us as a Program Manager to make a greater impact through your technical expertise and people skills. This could be the ideal chance to step up into your first Senior level role. Make your mark in Underwriting AIG underwriting teams help to find insurance solutions in areas including Financial Lines, Property, Casualty, Specialty Lines, Cyber, Multinational Clients, and High Net Worth individuals. We are reimagining how we help customers to manage risk, transforming our operating model, and reshaping our role responsibilities and career pathways. The goal is to unlock the full potential in each colleague – empowering our people to grow as insurance professionals and add more value to our customers and AIG. The Program Manager will report to the Head of North America A&H Underwriting and will be responsible for leading new and existing Accident and Health programs.  The Program Manager must be detail-oriented and have deep...

Job Description Are you looking for your next opportunity? Sompo has a unique opportunity for a VP, Territory Manager in our U.S. Environmental Insurance team. Location: This position will be based out of our Chicago office. We strive for collaboration, which is why we offer a work environment where our employees thrive and develop long-lasting careers. Our business, your impact, our opportunity: As the VP Territory Manager, you will lead an assigned underwriting territory for the Central U.S. market. You will build and manage partnerships with agents, brokers, and other distribution partners, leveraging strategic thinking to develop and maintain a strong pipeline of opportunities that supports profitable growth in Sompo’s Environmental business. You will underwrite both Environmental Pollution and Casualty accounts within your authority level and established guidelines while partnering across functions to deliver strong portfolio performance. Our...

Company Argo Group Argo Group is an underwriter of specialty insurance products in the property and casualty market. Argo offers a full line of products and services designed to meet the unique coverage and claims-handling needs of businesses. The Argo entities are wholly-owned subsidiaries of Clearbrook Group Holdings Inc. Job Description Summary: To provide strategic guidance and direction to the underwriting business units in regard to business development, underwriting excellence, and operational/shared services to promote profitable underwriting results. Responsible for driving profitable growth for assigned product or territory. Collaborates with executive management to develop strategic and tactical initiatives to reach the organization’s goals. The primary duties and responsibilities of the role are: · Identify and support profitable new business and product opportunities. · Identify strategic agencies and facilitate effective partnerships with...

Company Argo Group Argo Group is an underwriter of specialty insurance products in the property and casualty market. Argo offers a full line of products and services designed to meet the unique coverage and claims-handling needs of businesses. The Argo entities are wholly-owned subsidiaries of Clearbrook Group Holdings Inc. Job Description A Brief Overview Argo Group currently has a challenging opportunity for an Underwriting Technical Specialist, Primary Casualty to join our team. The primary purpose of this position is to actively participate in the production underwriting, marketing, and processing of assigned lines of business. May have responsibility over an assigned region or niche area. The role will work onsite (5 days per week) at our Chicago office location. The primary duties and responsibilities of the role are: Actively participate in the achievement of monthly and annual profitability and production goals and objectives for assigned...

What part will you play? If you’re looking for a place where you can make a meaningful difference, you’ve found it. The work we do at Markel gives people the confidence to move forward and seize opportunities, and you’ll find your fit amongst our global community of optimists and problem-solvers. We’re always pushing each other to go further because we believe that when we realize our potential, we can help others reach theirs. Join us and play your part in something special! The primary purpose of this position is to underwrite new business and renewals in a profitable manner and according to authority level and established guidelines, and participate in special projects having an impact on the business. Assigned larger and more important agents/brokers. Utilize underwriting tools to determine accurate classifications, rates, and premium charges. Understand state laws, including cancellation and non-renewal, within assigned territory to properly transact business within each...