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Welcome to Lindsay Cross Financial

Your trusted partner for all things insurance and financial success

Our Mission

Our mission is to serve our communities with integrity, transparency, and care.

We help anyone and everyone navigate insurance with clear guidance, honest answers, and a commitment to doing what's right, every time.

Our Core Offerings

Medicare

Our team can help you navigate the complexities of Part A & B, find policies to cover gaps (Advantage plans or Supplements), and stay updated on the industry. We offer a variety of plans to fit your needs and budget to make sure that you are protected.

Prescription Drug Coverage

Prescription Drugs can be some of the more tedious and frustrating plans to navigate. We help you choose the right combination of plan and pharmacies to make sure you never overpay for your prescriptions.

Dental, Hearing, and Vision

Ideal for filling healthcare gaps – these services aren't typically included in standard medical insurance. Many plans offer no waiting periods on preventative care, set annual benefit limits, and allow you to choose in- or out-of-network providers. They're flexible, affordable, and designed to keep your mouth, eyes, and ears in top condition.

Health Insurance

Whether you are moving on from group health coverage, looking for coverage for a spouse after moving to Medicare, or just shopping plans, we can help you see what this coverage looks like in your area and get you set with a plan that works for you.

Life Insurance

Secure your family's financial future with life insurance. We offer term life, whole life, and universal life policies. Our team can help you determine the best coverage amount and type for your situation.

401K Rollovers and Retirement Planning

401K rollovers move funds from your old employer plan into a qualified retirement account without triggering taxes or penalties. Plan your retirement with Lindsay Cross Financial. We offer a range of retirement planning options to help you achieve your long-term financial goals.

Our Services

Comprehensive financial solutions tailored to your needs

Interested in any of these services? We're here to help!

Contact us today for a personalized consultation about your financial needs.

Get in Touch

Or schedule a consultation now

Life Insurance

  • Term Life

    Options for 1, 5, 10, 15, 20, 25, 30, 35, & 40 year terms

  • Universal Life

    UL, GUL, and IUL options available

  • Whole Life

    Final Expense and Traditional policies

Annuities

  • 401k Rollover
  • Retirement Planning
  • Safe Money Accounts

    Upside potential without downside risk

Hospital Indemnity Plans

Comprehensive reimbursement for:

  • Hospital Stays
  • Ambulance Services
  • Emergency Room Visits

Long Term Care

  • Coverage for:
    • Nursing Home Care
    • Home Health Care
    • Assisted Living Facility
  • Hybrid LTC/Life Insurance options available

Critical Illness Coverage

Protection against serious conditions including:

  • Cancer
  • Heart Attack
  • Stroke
  • And more

Medicare Supplements

  • Plan G

    100% coverage of Medicare Approved Charges after Part B Deductible

  • No Networks - Freedom to choose your providers

Medicare Advantage Plans

  • Zero Premium options available for most plans
  • Extra Benefits Include:
    • Dental Coverage
    • Vision Care
    • Hearing Services
    • OTC Benefits
    • Gym Memberships
  • Network coverage based on county

Prescription Drug Plans

Customized plans varying by:

  • County location
  • Specific prescriptions needed

Dental, Vision, and Hearing

  • Available as individual plans
  • Combined package options

Accident Medical / Accident Death

Financial protection with benefits paid in the event of an accident

Meet Our Team

Jeremiah Cross's Photo

Jeremiah Cross

Hello, I'm Jeremiah Cross, an independent insurance professional helping individuals and families make confident, informed decisions about their healthcare and financial futures.

I hold a degree in Economics from Arizona State University, which shapes how I approach insurance: analytically, transparently, and with a strong focus on long-term outcomes. I work primarily with Medicare and life insurance, helping clients understand their options without pressure or confusion.

I proudly serve the Chicagoland area as well as Central Illinois, working with clients both in person and remotely to make the process as convenient as possible.

Schuyler's Photo

Schuyler Lindsay

I was born and raised in Central Florida and completed my education at Eastern Illinois University before ultimately settling in Chicago. Along the way, I built a strong background in sales and client-focused roles, where I learned the importance of listening, clear communication, and earning trust.

I entered the Medicare and insurance field to help people navigate complex choices with confidence. Medicare isn't one-size-fits-all, and my approach is simple: provide clear education, honest guidance, and personalized support – without pressure.

My goal is to help clients understand their options and choose coverage that truly fits their needs, while being a dependable resource they can rely on year after year.

Contact Us

Let's discuss your financial future

Send us a Message

Get in Touch

Schuyler Lindsay

Phone: (773) 758-2028
Email: stl.insurance94@gmail.com

Jeremiah Cross

Phone: (464) 927-9210
Email: jdcross1547@gmail.com

Business Hours

Monday - Friday: 8:00 AM - 8:00 PM
Saturday - Sunday: 8:00 AM - 2:00 PM

Schedule a Consultation

Book an appointment with Calendly

Frequently Asked Questions

Please reach us if you cannot find an answer to your question.

You can file a claim by contacting us directly or using your carrier website.

Your insurance premium may be impacted by your age, health, driving record, credit score, and chosen coverage. Contact us for details on your requested insurance.

Medicare's Annual Enrollment Period begins October 15th through December 7th.

Most commonly used by people age 65 or older, some younger people are eligible for Medicare, too. Those include people with disabilities, permanent kidney failure and amyotrophic lateral sclerosis (Lou Gehrig's disease). Medicare helps with the cost of health care, but it does not cover all medical expenses or the cost of most long-term care.

If your Medicare card was lost, stolen, or destroyed, you can request a replacement online at Medicare.gov. You can print an official copy of your card from your online Medicare account or call 1-800-MEDICARE (1-800-633-4227 TTY 1-877-486-2048) to order a replacement card to be sent in the mail.

Life insurance can help cover:

  • Co-signed debt including student loans
  • Mortgages
  • College expenses for the kids
  • Living expenses for your family
  • Stay-at-home labor expenses (cooking, cleaning, etc.)
  • Burial expenses
  • Loans from family members
  • Estate taxes that your heirs must pay for other assets

Creditable coverage is prescription drug coverage (for example, from an employer, union, TRICARE, Indian Health Service, or the Department of Veterans Affairs) that is expected to pay, on average, at least as much as Medicare's standard prescription drug coverage. Consumers with creditable coverage when they become eligible for Medicare can generally keep that coverage without paying a penalty if they decide to enroll in Medicare prescription drug coverage later.

The organization providing the prescription drug coverage must inform the consumer annually (generally in a letter or organization newsletter) if the prescription drug coverage is creditable coverage. The consumer will need this information if they later enroll in a Medicare Plan that provides Part D prescription drug coverage.

If a consumer does not enroll in Part D coverage when they are first eligible, or if they have a break in Part D coverage of 63 consecutive days or longer, they may be subject to a Part D late enrollment penalty (LEP). The Part D LEP is required by law and will be calculated by CMS and added to the consumer's monthly Part D premium for as long as they are enrolled Part D coverage, even if the consumer enrolls in a $0 premium plan. To help ensure a positive consumer experience, it is important that consumers understand what the LEP is and that it will apply regardless of which carrier or plan the consumer chooses.

Note: The LEP may be reduced or eliminated if the consumer qualifies for the Low-Income Subsidy Program (i.e., Extra Help).

The Part B late enrollment penalty is 10% of the monthly Part B premium added on to your premium every month for the remainder of your life. Each year you do not have Part B in place when you are supposed to is another 10% added. These are lifetime penalties.

Upcoming Events

Example of our Medicare seminar presentations

Join us at one of our informative Medicare seminars

Waukegan Community Resource Fair

Waukegan Community Resource Fair

Location:

Waukegan Public Library
128 N County St. Waukegan, IL 60085

Date & Time:

Friday, February 13th
2:00 PM - 4:00 PM

Turning 65 Medicare Seminar - Kankakee

Turning 65 Medicare Seminar

Location:

Kankakee Public Library
304 N Industrial Ave Kankakee, IL 60901

Date & Time:

Tuesday, March 3rd & Wednesday, March 4th
4:30 PM - 6:30 PM

Turning 65 Medicare Seminar - Waukegan April

Turning 65 Medicare Seminar

Location:

Waukegan Public Library
128 N County St. Waukegan, IL 60085

Date & Time:

Monday, April 20th & Tuesday, April 21st
5:30 PM - 7:30 PM

Turning 65 Medicare Seminar - Lisle August

Turning 65 Medicare Seminar

Location:

Corporetum Office Campus - Lisle
550 Warrenville Rd Lisle, IL 60532

Date & Time:

Monday, August 3rd & Tuesday, August 4th
5:00 PM - 7:00 PM

Turning 65 Medicare Seminar - St. Charles

Turning 65 Medicare Seminar

Location:

Pottawatomie Community Center
845 N 2nd Ave St. Charles, IL 60174

Date & Time:

Monday, October 5th
5:30 PM - 7:00 PM

Turning 65 Medicare Seminar - Waukegan October

Turning 65 Medicare Seminar

Location:

Waukegan Public Library
128 N County St. Waukegan, IL 60085

Date & Time:

Monday, October 19th & Tuesday, October 20th
5:30 PM - 7:30 PM

Turning 65 Medicare Seminar - Kankakee November

Turning 65 Medicare Seminar

Location:

Kankakee Public Library
304 N Industrial Ave Kankakee, IL 60901

Date & Time:

Monday, November 9th & Tuesday, November 10th
4:30 PM - 6:30 PM

Turning 65 Medicare Seminar - Lisle November/December

Turning 65 Medicare Seminar

Location:

Corporetum Office Campus - Lisle
550 Warrenville Rd Lisle, IL 60532

Date & Time:

Monday, November 30th & Tuesday, December 1st
5:00 PM - 7:00 PM