Photo by Scott Graham<\/a> on Unsplash<\/a> <\/p>\n Chubb: Decades of Dividend Growth Backed by Cash Generation <\/p>\n Chubb Limited (NYSE:CB) recently declared a quarterly dividend of $1.02 per share, keeping the payout unchanged after a 5.2% increase earlier in 2026. That increase brought the annual dividend to $4.08 per share and marked the company’s 33rd consecutive year of dividend growth. <\/p>\n That history matters for income investors. Chubb Limited (NYSE:CB) has raised its dividend through different insurance cycles, including periods of severe catastrophe losses, economic weakness, and changing interest rates. Its cash flow also helps explain how the company has maintained that record. Chubb generated $12.8 billion in operating cash flow in 2025, compared with $16.2 billion in 2024 and $12.6 billion in 2023. It paid $1.5 billion in common-stock dividends during the year. <\/p>\n Chubb Limited (NYSE:CB) generated more than eight times the cash needed to cover its 2025 common dividends. That gives the company plenty of room to return capital to shareholders while investing in the business and maintaining its financial strength. <\/p>\n Chubb is also benefiting from the higher investment-income environment across the industry. Its large investment portfolio has generated stronger investment income in recent years, giving the company another source of earnings alongside underwriting. <\/p>\n Travelers: Stronger Recent Dividend Growth and Rising Cash Flow <\/p>\n The Travelers Companies, Inc. (NYSE:TRV) has a similar story, but its recent dividend growth has been stronger. The insurer currently pays $1.25 per share each quarter, or $5.00 annually, after raising the dividend 13.6% earlier in 2026. <\/p>\n Story Continues <\/p>\n Travelers has increased its dividend for 21 consecutive years. That is shorter than Chubb’s 33-year streak, but it still gives the company more than two decades of uninterrupted dividend growth. Travelers’ cash-flow trend is also encouraging. Operating cash flow rose to $10.6 billion in 2025 from $9.1 billion in 2024 and $7.7 billion in 2023. That steady increase gives the dividend some added support. <\/p>\n The Travelers Companies, Inc. (NYSE:TRV) generated considerably more operating cash than it needed to fund its common dividend. That leaves management room to keep raising the payout while investing in the business and returning additional capital through share repurchases. <\/p>\n The company’s latest results support that picture. In the second quarter of 2026, The Travelers Companies, Inc. (NYSE:TRV) reported a sharp increase in profit as catastrophe losses declined and investment income increased. Net investment income rose 13.6% to $1.07 billion, while underwriting income jumped to $1.74 billion from $1.02 billion a year earlier. <\/p>\n That combination matters for dividend investors. Travelers is not relying on investment income alone to fund its payout. Underwriting profitability and income from its large investment portfolio both contribute to earnings and help support the dividend. <\/p>\n Which Dividend Looks Stronger? <\/p>\n The two insurers are fairly close from an income perspective, but their strengths are different. Chubb Limited (NYSE:CB) has the longer dividend-growth record. Its 33-year streak gives it the edge when it comes to consistency. The company has also shown that it can keep increasing its payout without putting too much pressure on earnings or cash flow. <\/p>\n The Travelers Companies, Inc. (NYSE:TRV) has been more aggressive with recent dividend increases. Its 13.6% hike in 2026 was significantly larger than Chubb’s 5.2% increase. The cash-flow trend is encouraging too, with operating cash generation rising for three consecutive years through 2025. <\/p>\n The broader industry backdrop still favors both companies, at least for now. U.S. P&C insurers produced strong underwriting results in 2025, and first-quarter 2026 underwriting income remained robust. Investment income also continued to support earnings. <\/p>\n There are still risks to consider. Insurance pricing is beginning to soften, while catastrophe losses, social inflation, and liability claims could put pressure on margins. As pricing becomes less favorable, underwriting discipline will matter even more. <\/p>\n Conclusion <\/p>\n For dividend-growth investors, both Chubb and Travelers remain attractive insurance stocks, but they offer different strengths. Chubb is the better fit for investors who place the greatest value on a long, proven dividend-growth record. Thirty-three consecutive years of increases show that the company can grow shareholder payouts through different insurance cycles. Its strong operating cash generation also gives it room to keep increasing the dividend. <\/p>\n The Travelers Companies, Inc. (NYSE:TRV) may appeal more to investors looking for faster recent dividend growth and improving cash generation. Its 13.6% dividend increase in 2026 was much stronger than Chubb’s, while operating cash flow has risen steadily over the past three years. <\/p>\n Neither stock needs a high yield to be attractive to a long-term income investor. The bigger point is the combination of durable insurance operations, strong cash generation, disciplined capital allocation, and the ability to raise dividends over time. <\/p>\n For investors building a portfolio around dividend growth rather than chasing the highest current yield, both Chubb and Travelers deserve consideration. Chubb has the stronger dividend-growth record, while Travelers currently has more momentum behind its dividend increases. <\/p>\n While we acknowledge the potential of CB and TRV as an investment, we believe certain AI stocks offer greater upside potential and carry less downside risk. If you’re looking for an extremely undervalued AI stock that also stands to benefit significantly from Trump-era tariffs and the onshoring trend, see our free report on the\u00a0<\/a>best short-term AI stock<\/a>. <\/p>\n READ NEXT: Does LyondellBasell Industries (LYB) Still Make Sense for Dividend Investors?<\/a> and American States Water Company (AWR): This Quiet Dividend King Keeps Raising the Bar<\/a> <\/p>\n<\/a> Chubb and Travelers: Comparing Dividend Growth in the Insurance Sector <\/p>\n