Underwriter Jobs in Chicago, IL
Underwriter jobs in Chicago are concentrated in the Loop, River North, and Schaumburg, across commercial insurance, life and health, and mortgage lending, with strong demand from carriers, banks, and specialty finance firms. Employers actively hiring include Chubb, Liberty Mutual Insurance, and The Hartford. Find a role that fits below and apply directly.
Find Underwriter JobsOverview
Showing 5 of 38+ Underwriter jobs








Crum & Forster (C&F), with a proud history dating to 1822, provides specialty and standard commercial lines insurance products through our admitted and surplus lines insurance companies. C&F enjoys a financial strength rating of "A+"(Superior) by AM Best and is proud of our superior customer service platform. Our claims and risk engineering services are recognized as among the best in the industry.
Our most valuable asset is our people: more than 2000 employees in locations throughout the United States. The company is increasingly winning recognition as a great place to work, earning several workplace and wellness awards, including the 2024 Great Place to Work® Award for our employee-first focus and our steadfast commitment to diversity, equity and Inclusion.
C&F is part of Fairfax Financial Holdings, a global, billion dollar organization. For more information about Crum & Forster, please visit our website: www.cfins.com.
Job Description:Senior Underwriter - Commercial Surety Midwest (remote position and candidates should be located in Upper Midwest - Illinois, Wisconsin, Minnesota, Indiana, Ohio)
A Senior Underwriter is accountable for Commercial Surety product underwriting that contributes to the achievement of the Commercial Surety business plan including new business, renewal retention, pricing and profitability. This role reports directly to the Regional Underwriting Manager of Commercial Surety and will work closely with the Regional Underwriting Manger to foster agency/broker relationships and develop a profitable book of business.
Essential Job Functions and Responsibilities
- Responsible for risk selection/rejection, pricing, retention, growth, and profitability within scope of authority and per divisional objectives.
- Receives and analyzes submissions, assesses risk quality and determines terms in accordance with company guidelines.
- Applies underwriting rules and guidelines, rating manual rules, and insurance laws and regulations.
- Makes recommendations on risks over authority.
- Enters, maintains and monitors accounts using underwriting, analysis, and desktop systems
- Uses independent judgment and initiative to support business goals.
- Prepares effective internal and external communications on underwriting issues.
- Develops a book of commercial surety business with select brokers/agents and maintains effective business relationships with external customers in order to attract and retain profitable business.
- Visits producers and principals in order to retain existing accounts, survey exposures, build and maintain business relationships, and develop new opportunities in support of divisional objectives.
Job Requirements
- 6+ years of commercial experience is required.
- Bachelor’s degree or equivalent is required, preferably in Business, Finance, Accounting or a related field.
- Must have strong communication skills to build and leverage excellent customer relationships and to successfully market products.
- Sales mindset for creating and following through on pipeline opportunities that contribute to new business goals and budget objectives.
- Excellent communication, interpersonal and presentation skills.
- An ability to think analytically about business problems, make recommendations and propose solutions.
- A high energy, self-starter, who is resilient and has an entrepreneurial spirit.
- Demonstrates solid time, organizational, and desk management skills.
- Goal-oriented mind set, delivers on goals and objectives.
- Microsoft Office experience and the ability to learn new applications are a must.
- Travel and a valid driver's license required.
We value inclusivity and diversity. We are committed to equal employment opportunity and welcome everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, or Veteran status. If you require special accommodation, please let us know.
For California Residents Only: Information collected and processed as part of your career profile and any job applications you choose to submit are subject to our privacy notices and policies, visit https://www.cfins.com/onlineprivacypolicy/ca/noticeatcollection/ for more information.
Crum & Forster is committed to ensuring a workplace free from discriminatory pay disparities and complying with applicable pay equity laws. Salary ranges are available for all positions at this location, taking into account roles with a comparable level of responsibility and impact in the relevant labor market and these salary ranges are regularly reviewed and adjusted in accordance with prevailing market conditions. The annualized base pay for the advertised position, located in the specified area, ranges from a minimum of $74,900 to a maximum of $140,700. The actual compensation is determined by various factors, including but not limited to the market pay for the jobs at each level, the responsibilities and skills required for each job, and the employee’s contribution (performance) in that role. To be considered within market range, a salary is at or above the minimum of the range. You may also have the opportunity to participate in discretionary equity (stock) based compensation and/or performance-based variable pay programs.
- Flexible work arrangements.
- Competitive compensation package.
- Generous 401K employer match.
- Employee Stock Purchase plan with employer matching.
- Generous Paid Time Off.
- Excellent benefits that go beyond health, dental & vision. Our Wellness programs focus on your family’s complete wellness, including your physical and mental wellbeing
- A core C&F principle is that you manage your career. To support your development, we have a wealth of ways for you to keep learning, including tuition reimbursement, industry related certifications and professional training available to you.
- A dynamic, ambitious, fun and exciting work environment.
- A spirit of social responsibility, matching donation program, volunteer opportunities, and an employee driven corporate giving.
#LI-JA1
See All 38 Underwriter Jobs in Chicago
Find roles in Chicago that match your experience and apply in just a few clicks.
Find Underwriter JobsUnderwriter Job Market in Chicago
Who's Hiring
- Chubb5

- Liberty Mutual Insurance5

- The Hartford2

- Bank of America2

- Zurich Insurance2

Top Industries Hiring
- Insurance32
- Banking & Financial Services5
- Construction & Real Estate1
Underwriter Jobs in Chicago: Frequently Asked Questions
How do I get a underwriter job in Chicago?
The strongest path into Chicago underwriting runs through the Loop and Schaumburg, where commercial property and casualty carriers, regional banks, and specialty lenders concentrate their hiring. Candidates with commercial lines exposure, mortgage underwriting experience, or a background in financial analysis get the most callbacks. Familiarity with Chicago's dense commercial real estate and mid-market business sectors gives you a genuine edge over generalist applicants targeting this market.
Which companies hire underwriters in Chicago?
Employers hiring underwriters in Chicago right now include Chubb, Liberty Mutual Insurance, and The Hartford, based on current listings on Migrate Mate as of June 2026. Chicago's market is particularly active among large regional carriers, national insurers with Midwest headquarters, and community banks with strong commercial lending portfolios.
Are there remote underwriter jobs in Chicago?
Yes, though it depends heavily on the specialty: mortgage and personal lines underwriting tend to be more remote-friendly than commercial or specialty lines roles that require hands-on account review. About 22% of underwriter openings tied to Chicago are remote or hybrid as of June 2026, reflecting a mix of options across employer types. Larger carriers headquartered in the Loop and Schaumburg are most likely to offer structured hybrid arrangements.
How can I get a underwriter job in Chicago with little or no experience?
The most realistic entry point in Chicago is an underwriting assistant or analyst role at one of the regional carriers or community banks operating in the Loop or near O'Hare. These positions involve reviewing submissions, spreading financials, and supporting senior underwriters, and they convert to full underwriter titles quickly in active Chicago offices. A background in insurance coursework, banking, or credit analysis strengthens your application, and pursuing an Associate in Commercial Underwriting designation signals commitment to local hiring managers.
Which industries hire the most underwriters in Chicago?
Chicago underwriter roles concentrate in Insurance, Banking & Financial Services, and Construction & Real Estate, based on current listings on Migrate Mate as of June 2026. Chicago's position as a Midwest financial hub and home to major insurance carriers, futures exchanges, and a large commercial real estate market makes it one of the most active underwriting labor markets in the country outside of New York.
Related Jobs in Illinois
See All 38 Underwriter Jobs in Chicago
Find roles in Chicago that match your experience and apply in just a few clicks.
Find Underwriter Jobs