

SAVINGS UPDATE!
We’re saving our clients over $2 million in annual premiums!
For people under 65, Open Enrollment for health insurance is over. So how do you get health insurance if you need it?
Don’t go to healthcare.gov. The national system is woefully ignorant about conditions in Illinois.
Call Jerry Pearlstein Insurance 847-362-8888 for expert help getting Special Enrollment coverage including assistance paying premiums and sharing costs. Our services are free and confidential. From the first conversation, through application and whenever you need us, we’re here to help you.
Congratulations to Jerry Pearlstein for Earning 2025 Marketplace Circle of Champions Elite Status!
Latest Health News
The Marketplace Circle of Champions Recognizes Jerry Pearlstein Insurance for More Than 100 Enrollments
Jerry Pearlstein Insurance has been honored by the Health Insurance Marketplace® as an Elite member in the 2025 Marketplace Circle of Champions. This Centers for Medicare & Medicaid Services (CMS) … Continue reading →
We Saved Our Clients Over $2 Million In Annual Premiums In 2024

Jerry S. Pearlstein uniquely specializes in health insurance with over 20 years experience.

Multiple Healthcare.gov award winner, including letters of commendation from the CMS Critical Cases unit.

Unlike online services, we make sure your doctors will accept the insurance you choose.

When ACA plans don't work, we may have other insurance that does.

Unlike online services, we get all the info needed for the premium assistance and cost sharing you are entitled to.

Unlike online services, we're always available to answer all your questions and concerns.
COBRA & Other Alternatives
ON COBRA?
Now’s the time to see if there are alternatives for 2025.
Join our Zoom seminar “COBRA & Alternatives” every first and third Wednesdays at 10:30 a.m. by emailing for the link: rbloomfield@jpearlsteinltd.com.
This program is designed to assist you in understanding your options in the complex landscape of health insurance after separation from your employer. We’ll discuss how the COBRA program works as well as the options available in Private Health Insurance (PHI) so you can make the best decision for you and your family.

Nationally Recognized, Award-Winning Healthcare!

What healthcare.gov says about Jerry S. Pearlstein Insurance
“We are continually impressed by the dedication and commitment you show to consumers during the busy Open Enrollment Period.”
Actually, that’s how we treat folks all the time. Under 65. Medicare. 1-50 Groups.

Senior Medicare True Blue Award Recipient
With over 400 Medicare Supplement clients, Jerry Pearlstein is honored to receive this award for our dedication and service.
We stay up-to-date on Medicare information, services and benefits. In 2024 we determined clients eligible for new Supplements, contacted them and ultimately saved them an average of 25% on their monthly premiums.
If you are turning 65, or want to change your Medicare Supplement, call us at 847-362-8888.
What Are Clients Are Saying
Thank you—to both you & Jerry for going the extra miles with me to get coverage. My husband is so EXCITED to be able to see his old doctors and & get the proper tests done again. You’re both AMAZING!!
A pleasure to work with!
They really know their business, I trust them totally with my insurance needs!
Jerry and Rebecca have been providing our family excellent, practical advice on our insurance needs for years, along with top flight service. We are extremely pleased and highly recommend them.
Jerry and Rebecca are fantastic!! The Jerry S. Pearlstein agency has provided excellent service and advice in arranging health plans for my family members. We are extremely grateful, and recommend JSP to all of our friends working on their own health plans.
Words cannot describe my gratitude for your continuous loyalty and perseverance in assisting me with my Health Insurance needs.
There is nothing more stressful than having to sort through health insurance needs on an annual basis, especially when the market is in constant flux. Having Jerry and Rebecca as our broker eliminates 99% of that. They go to bat for our family as well as our business whenever needed. I can’t recommend them enough!
Needed help navigating insurance. Jerry’s experience and knowledge were top notch and extremely helpful. He helped me understand the process, find the right insurance, and setup a conference call to complete the registration process. We have insurance and saved a lot of money because of his help. I highly recommend his services.
I just want you to know that signing up for the Blue Cross Blue Shield health insurance plan this year was the smoothest experience we’ve ever had since Obamacare started.
Jerry has helped my family navigate through the ACA twice now. He is a great resource and the entire team truly cares about their clients.
Great service. Very friendly. Excellent follow-through.
I am very grateful of your time, resourcefulness and positive attitude!
I wanted to thank you both for your assistance in helping me to find insurance coverage given my circumstances.
Jerry Pearlstein is an outstanding resource for your Healthcare Insurance needs. The Healthcare government Marketplace is complex and confusing, Jerry’s experience makes the entire process simple and easy. I highly recommend Jerry if you have any Healthcare Insurance needs.
The gold standard of (Medicare) supplemental insurance… a lot more value and invaluable peace of mind.
It was a pleasure working with Rebecca. She provided me with the options for healthcare that met my needs
Thank you so much for your help with Tom’s insurance. We couldn’t have done it without you!
Thank YOU BOTH SO MUCH! You’ve got 6 very relieved and happy people!
Jerry and Rebecca made the entire process very easy. We also appreciate that they are only a phone call away during the year if we have any issues.
Jerry and Rebecca have helped me navigate the annual healthcare enrollment for the past 3 years, including Healthcare.gov. They have helped me select the appropriate ACA policies for me as well as the Medicare policies for my husband. They are caring and quick to respond to any questions I might have throughout the year. I wholeheartedly recommend their agency.
Thanks Jerry & Rebecca for your knowledge, professionalism and kindness. We can always tell you have our best interests in mind. We never feel rushed and you always address any questions and concerns. You put our minds at ease knowing it will be done right.
I’d like to thank Rebecca Bloomfield and Jerry Pearlstein from Jerry S. Pearlstein Insurance Ltd. for their help in selecting an appropriate health-care plan and facilitating the completion/submission of my application.
He presented me different plan options and then asked if I would like him to be my agent to shepherd my application through the system. I said, “Yes!” He did so…professionally, kindly, and effectively.
Everything got squared away in short order.
Thank you, jerry and Rebecca, for helping me find the appropriate health-care plan. I will recommend your agency to other people (especially entrepreneurs) that need help buying a suitable health-care plan.
Thank you! We appreciate your quick and thorough service!
You’re far and away the best insurance folk I’ve worked with. Really. Thank you
Jerry and Rebecca, at Pearlstein Insurance, have provided me with great service and the best available insurance products for more than 10 years. They always take the to time to evaluate my personal needs to ensure I get the best coverage at the best prices for what I need. I feel very secure entrusting Jerry and Rebecca with my health care insurance decisions.
Jerry and Rebecca have provided incredible support in navigating MarketPlace insurance for my first time. Jerry took the time twice to be on my calls with the government and handled all the information! Rebecca has helped in understanding insurance options after leaving a job. Both are very responsive and trustworthy. They make you feel like they are looking out for you. Very highly recommend them!
The support I receive from Jerry and Rebecca is unparalleled. They go above and beyond providing customized guidance and recommendations while seeing me as an individual. They are prompt, extremely knowledgeable, and are dedicated to ensuring my needs are fully met. I highly recommend them!
Jerry and Rebecca are knowledgeable and helpful. I appreciate their professionalism.
I have been with Pearlstein Insurance for about ten years and they are wonderful. The family has grown and our coverage is superb. Jerry and Rebecca have helped in a professional and highly supportive manner.
This was an amazing service! Jerry was so helpful and knowledgeable. He guided me through the whole process. I recently lost my job due to Covid. Jerry helped me reduce my monthly premiums by 70%. Never would have figured this out without him. Highly recommend!