Group health, Medicare & individual insurance — made simple.
Ascend Insurance Planning is an independent agency helping small and mid-size businesses (2–500 employees), individuals, and Medicare-eligible families in Chicago, IL compare plans across top carriers — with one licensed team guiding you from quote to enrollment.
What We Do
At Ascend Insurance Planning, we specialize in coordinated insurance coverage — including group health insurance for businesses, Medicare planning, individual & family marketplace plans, and personal life, disability, and long-term care insurance. We help individuals, families, and employers navigate complex coverage choices to secure the right protection at the right cost.
Why It Matters
Health costs, a disabling injury, or a long-term care need are some of the largest and most unpredictable expenses a person or business will face. A gap in coverage — the wrong Medicare plan, no disability protection, an under-insured group plan — means real financial exposure right when you can least afford it. We make sure every policy you hold is actually the right fit, not just the first one you were offered.
How We Help
Our Services
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Group Health Insurance
Employer-sponsored plans, 2–500 employees.
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Medicare
Advantage, Supplement & Part D.
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Individual & Family Marketplace
ACA marketplace plans.
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Life Insurance
Term, Whole & Universal.
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Disability Insurance
Short-Term & Long-Term.
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Long-Term Care Insurance
Traditional, Hybrid & Group LTC.
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Group Health Insurance for Small & Mid-Size Businesses
If you have between 2 and 500 employees, Ascend helps you build a group health plan that fits your budget and your team. We compare medical, dental, and vision options across the carriers licensed in your state, then stay on for enrollment, renewals, and the claims questions that come up in between.
Most states define "small group" coverage as 50 or fewer full-time-equivalent employees (up to 100 in a few states). Groups above that move into the large-group market — the plan design changes, but our process doesn't.
Get a group health quoteWhat's Included
- Medical, dental & vision plan design and carrier comparisons
- Section 125 / cafeteria plan setup support
- Renewal shopping every year, not just at signup
- COBRA and compliance guidance
- One point of contact for your employees' questions
Medicare: Advantage, Supplement & Part D Plans
Turning 65 or already on Medicare? We walk you through Original Medicare, Medicare Advantage (Part C), Medicare Supplement (Medigap), and Part D prescription drug plans in plain language, at no cost to you — our advice doesn't change based on whether you enroll through us.
Your Initial Enrollment Period runs 7 months around your 65th birthday. After that, the Annual Enrollment Period (October 15 – December 7) lets you switch plans for the following year, and the Medicare Advantage Open Enrollment Period (January 1 – March 31) gives current Advantage members one more chance to change course.
Compare Medicare plansWe Help You Decide
- Advantage vs. Supplement, based on your doctors and prescriptions
- Which Part D plan covers your medications
- When you can enroll or make changes without a penalty
- Whether a Medicare Supplement plan is worth the extra premium
Individual & Family Marketplace (ACA) Insurance
Self-employed, between jobs, or without access to an employer plan? We help individuals and families compare ACA marketplace coverage and check whether you qualify for a premium tax credit that lowers your monthly cost.
Open Enrollment generally runs November 1 through January 15 nationally, though some state exchanges set their own deadlines. Outside that window, a qualifying life event — losing other coverage, moving, marriage, or having a baby — opens a Special Enrollment Period, typically 60 days long.
Get a marketplace quoteWhat We Help With
- Marketplace plan comparisons by doctor and prescription network
- Premium tax credit / subsidy estimates
- Enrollment during Open Enrollment or a qualifying life event
- Ongoing support after you're enrolled, not just at signup
Life Insurance: Term, Whole & Universal
Life insurance is about protecting the people who depend on your income — a spouse, kids, a business partner, or aging parents. We compare term life (temporary, budget-friendly coverage) against whole and universal life (permanent coverage that can build cash value) so you're not paying for more, or less, than you actually need.
Coverage amounts and health underwriting vary by carrier, so getting a few real quotes usually matters more than picking a brand name — that's the part we handle.
Get a life insurance quoteWhat We Help You Decide
- Term vs. permanent (whole/universal) life insurance
- How much coverage actually makes sense for your situation
- Health underwriting — what to expect and how to prepare
- Beneficiary and policy structure questions
Disability Insurance: Short-Term & Long-Term
Disability insurance replaces part of your income if an illness or injury keeps you from working — something health insurance doesn't cover. We compare short-term plans (weeks to months of coverage) and long-term plans (years, or until retirement age) so a temporary setback doesn't turn into a lasting financial one.
Many employer group plans include a base level of disability coverage — we can review what you already have and see whether it's enough, or whether an individual policy should fill the gap.
Get a disability insurance quoteWhat We Help You Decide
- Short-term vs. long-term disability coverage
- Whether your employer's group coverage is enough on its own
- Elimination periods and how long benefits actually last
- Own-occupation vs. any-occupation definitions
Long-Term Care Insurance
Long-term care — help with everyday activities due to age, illness, or injury — isn't covered by health insurance or Medicare beyond a short window. We compare traditional long-term care policies, hybrid life/LTC policies, and group long-term care options so a future care need doesn't fall entirely on you or your family.
Timing matters here more than almost any other coverage — premiums are generally lower, and approval easier, the earlier you apply.
Get a long-term care quoteWhat We Help You Decide
- Traditional vs. hybrid (life insurance + LTC) policies
- Group long-term care options through an employer
- How much daily/monthly benefit actually makes sense
- When to apply for the best rate and approval odds
Group Ancillary Benefits
Dental, vision, life, disability, and accident coverage layered onto any group plan — often at little to no added cost to the business.
Why Work With Ascend
How It Benefits You
When you work with Ascend Insurance Planning, one team reviews every layer of your coverage — group health, Medicare, individual or family marketplace, life, disability, and long-term care — instead of you piecing it together from several different agents.
- Protect What Matters Most — the right coverage for your health, income, and family, without paying for protection you don't need.
- Coordinated, Not Siloed — your group, Medicare, individual, life, disability, and long-term care coverage are reviewed together, so nothing overlaps and nothing gets missed.
- Simplified Decision-Making — we cut through deductibles, riders, elimination periods, and plan fine print to give you a clear, specific recommendation.
- One Team, Every Policy — a single point of contact for renewals, claims questions, and life changes across every policy you hold with us.
The result: coverage that actually works together — not a stack of separate policies you have to manage on your own.
Get Started
Get your free quote
Tell us a bit about your coverage needs and a licensed Ascend advisor will reach out within 24 hours — no obligation, no spam.
Prefer to talk it through?
Thanks — we've got it.
A licensed Ascend advisor will reach out within 24 hours. If you'd rather not wait, call us at 708.390.0034.
FAQ
Common questions about group, Medicare, individual & personal insurance
Updated regularly as rules and enrollment dates change.
Last updated: [Month Year]
Most states classify small-group coverage as 50 or fewer full-time-equivalent employees (up to 100 in California, New York, and Vermont). Groups above that move into the large-group market. Ascend works with businesses across that entire range — from 2 up to 500 employees.
No. Carriers set the same premium whether you enroll directly or through a licensed broker. Our compensation comes from the carrier, not from you, so there's no added fee for our help.
Medicare Advantage (Part C) bundles hospital, medical, and often drug coverage into one plan with a provider network, usually for a low or $0 premium. Medicare Supplement (Medigap) pairs with Original Medicare to cover out-of-pocket costs and works with any provider that accepts Medicare, typically for a higher monthly premium. The right fit depends on your doctors, prescriptions, and budget.
Your Initial Enrollment Period runs 7 months around your 65th birthday. After that, the Annual Enrollment Period (October 15 – December 7) lets you switch Medicare Advantage or Part D plans for the following year, and the Medicare Advantage Open Enrollment Period (January 1 – March 31) gives current Advantage members one more chance to switch.
Source: Medicare.gov
The Marketplace (Healthcare.gov or your state's exchange) is where individuals and families without employer coverage can compare and enroll in ACA-compliant plans, and check eligibility for premium tax credits that lower the monthly cost.
Source: HealthCare.gov
Yes, if you have a qualifying life event — losing other coverage, moving, marriage, or having a baby, among others — which opens a Special Enrollment Period, typically 60 days long.
Ancillary benefits are supplemental coverages — dental, vision, life, disability, and accident insurance — layered on top of a group medical plan to round out an employee benefits package.
It depends on how long you need the coverage and your budget. Term life covers a set period (often 10–30 years) at a lower cost and is usually enough if the goal is replacing income while you're working or paying off a mortgage. Whole and universal life cost more but last your entire life and can build cash value — worth considering for estate planning or lifelong dependents.
Many group plans include a base level of short- or long-term disability coverage, but it often replaces only 40–60% of income and may be capped well below your actual salary. We can review your existing group benefit and tell you honestly whether an individual policy is worth adding.
Long-term care insurance covers help with everyday activities — like bathing, dressing, or memory care — whether at home, in assisted living, or in a nursing facility, which Medicare only covers for a short window after a hospital stay. Premiums are generally lowest and approval easiest in your 50s and early 60s, before a health change can limit your options.
Fill out the quote form above or call us directly at 708.390.0034. A licensed advisor will follow up within 24 hours to review your options at no cost.
Reviewed by [REVIEWER NAME], Licensed Agent, IL License #[LICENSE NUMBER].
Why Ascend
We shop the market so you don't have to.
Ascend Insurance Planning compares carriers side by side and stays on after enrollment — for renewals, claims questions, and open enrollment, not just the sale.
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Alex Mau
Group Health Specialist
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Carmen Valentino
Medicare Specialist
"Ascend made our group health renewal easy. They put our options side by side, explained them in a way we could understand, and helped us save money. They even met with our employees to answer their questions instead of just sending them a plan and moving on. No pressure, just clear choices and awesome service!"
Ready to compare your options?
Get a free, no-obligation quote today.