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Find Medicare Insurance Agents Near You in Oswego, IL

Browse medicare insurance agents serving Oswego, Illinois. Updated 2026-07-14.

The top-rated medicare insurance agent in Oswego, Illinois is The Calder Agency: Allstate Insurance, rated 4.9 stars across 428 reviews. Other highly rated options include Janna Misek - State Farm Insurance Agent, Nicole Hupp: Allstate Insurance, Rick Weissenhofer - State Farm Insurance Agent. This directory lists 16 medicare insurance agents serving Oswego.

Showing 16 medicare insurance agents in Oswego, ILListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1The Calder Agency: Allstate Insurance2765 Walter Payton Memorial Hwy(630) 554-5252
2Janna Misek - State Farm Insurance Agent1136 Douglas Rd(630) 554-1540
3Nicole Hupp: Allstate Insurance4589 IL-71(630) 833-8100
4Rick Weissenhofer - State Farm Insurance Agent2261 Orchard Rd(630) 554-5277
5Holten Insurance AgencyBy appointment only - meeting location provided upon scheduling, 4913 Seeley St(630) 424-0200
6Zac Mcgrogan - State Farm Insurance Agent72 W Washington St(630) 554-8800
7Christina Reynolds Insurance Corp American Family Insurance103 Franklin St(630) 551-1784
8Tri-County Insurance Agency, Inc. "Bentley Agency"44 Monroe St(815) 200-5528
9VERONICA CONTRERAS: Allstate Insurance3408 Orchard Rd(630) 536-3090
10Hometowne Insurance4424 IL-71(630) 554-4040
CA
2765 Walter Payton Memorial Hwy
The Calder Agency: Allstate Insurance
Medicare Insurance Agent · Oswego, IL

The Calder Agency: Allstate Insurance, serving the Oswego, Illinois area, assists individuals with navigating Medicare insurance options. Their work focuses on helping clients understand plan details and enroll in coverage that fits their needs. This agency provides guidance through the complexities of the Medicare system for local residents. They also help with the annual enrollment period and Medicare Supplement plan selections.

JM
1136 Douglas Rd
Janna Misek - State Farm Insurance Agent
Medicare Insurance Agent · Oswego, IL

Janna Misek - State Farm Insurance Agent in Oswego, IL provides a range of Medicare insurance services, including assistance with plan selection, enrollment, and annual policy reviews to help clients navigate changing healthcare needs. Ongoing service includes personalized consultations to explain plan details, coverage options, and potential costs, ensuring clients understand their benefits throughout the year. The agency also offers support with claims questions and policy adjustments as circumstances evolve. It serves single-family homes, apartments, retail, and restaurants in the local area.

NH
4589 IL-71
Nicole Hupp: Allstate Insurance
Medicare Insurance Agent · Oswego, IL

Medicare-eligible individuals and their families in Oswego, Illinois turn to Nicole Hupp: Allstate Insurance for help navigating plan options. The agency assists clients with comparing Medicare Advantage, supplement, and Part D drug coverage to find suitable benefits. Services include annual enrollment support and plan evaluation. Guidance is tailored to each person’s health needs and budget. The office also serves seniors and pre-retirees in neighboring Montgomery and the greater Aurora area.

RW
2261 Orchard Rd
Rick Weissenhofer - State Farm Insurance Agent
Medicare Insurance Agent · Oswego, IL

Rick Weissenhofer - State Farm Insurance Agent in Oswego, IL, serves the Oswego area and surrounding communities, handling Medicare insurance plans for eligible individuals. The agency helps clients navigate plan options, including coverage for hospital and medical expenses. It works to match each person with a plan that fits their healthcare needs and budget constraints. The typical job is handled by first reviewing the client's current coverage, then explaining available plans from various carriers to find suitable Medicare options within the local network.

HI
By appointment only - meeting location provided upon scheduling, 4913 Seeley St
Holten Insurance Agency
Medicare Insurance Agent · Oswego, IL

At Holten Insurance Agency in Oswego, IL, clients choose either a one-time review to understand their current Medicare coverage or an ongoing partnership for annual plan updates. Comprehensive guidance is offered on Medicare Supplement and Advantage options, helping individuals navigate enrollment periods and compare plan features. Service appointments run on a one-time, scheduled, or as-needed basis to accommodate varying customer preferences.

ZM
72 W Washington St
Zac Mcgrogan - State Farm Insurance Agent
Medicare Insurance Agent · Oswego, IL

Zac Mcgrogan - State Farm Insurance Agent in Oswego, IL offers Medicare insurance guidance, helping clients navigate plan options and enroll. The agency also assists with other coverage needs, such as life and health policies, to protect individuals and families. Throughout the year, clients can rely on support for understanding benefits and making changes. As the annual enrollment period approaches, it helps residents review their current plans and adjust coverage to better match their changing health needs or budget.

CR
103 Franklin St
Christina Reynolds Insurance Corp American Family Insurance
Medicare Insurance Agent · Oswego, IL

As Oswego seniors review their options during the annual Medicare enrollment period, many seek clear guidance on plan choices. Christina Reynolds Insurance Corp, operating as American Family Insurance, provides local support for these decisions. The agency helps individuals compare Medicare Advantage, Supplement, and Part D drug plans suited to their healthcare needs and budgets. Focusing on personalized service available without traveling far, the company arranges an initial consultation to review each client’s current coverage and health circumstances. That step begins with a complimentary plan assessment to identify potential options.

TC
44 Monroe St
Tri-County Insurance Agency, Inc. "Bentley Agency"
Medicare Insurance Agent · Oswego, IL

Tri-County Insurance Agency, Inc., operating as the Bentley Agency, provides guidance on Medicare insurance options for individuals in the Oswego, Illinois area. The agency specializes in helping clients navigate Medicare supplement plans and prescription drug coverage to meet their healthcare needs. These services are available for those working in local offices, warehouses, and food service establishments, supporting a variety of commercial sectors with appropriate plan selection.

VC
3408 Orchard Rd
VERONICA CONTRERAS: Allstate Insurance
Medicare Insurance Agent · Oswego, IL

Veronica Contreras Allstate Insurance provides residential Medicare insurance services in Oswego, IL, helping clients navigate plan options for medical coverage. Commercial insurance solutions are also offered to local businesses. The agency serves clients throughout the Oswego area and surrounding communities. Each consultation focuses on explaining benefits, enrollment periods, and policy details clearly. Clients are encouraged to return for plan reviews during annual enrollment windows, and the office coordinates follow-up service between regular visits to adjust coverage as needs change.

HI
4424 IL-71
Hometowne Insurance
Medicare Insurance Agent · Oswego, IL

Hometowne Insurance, a Medicare insurance agent in Oswego, IL, is known for helping local seniors navigate their annual plan choices. It assists clients with comparing Medicare Advantage, Part D drug plans, and Medigap supplement policies to find coverage that fits their medical needs and budget. The agency focuses on explaining how different plans work alongside Original Medicare. An available specialty service it provides is coordinating the switch from employer retiree coverage to a personal Medicare plan during the initial enrollment period.

JB
123 W Washington St Ste 333
Jim Braddish - COUNTRY Financial Agent
Medicare Insurance Agent · Oswego, IL
(630) 553-7401
agents.countryfinancial.com/usa/il/oswego/jim-braddish
NM
5 Main St
N.M. Tripp Insurance Agency, Inc.
Medicare Insurance Agent · Oswego, IL
(630) 554-8831
trippinsuranceinc.com
NI
31 Kendall Point Dr Ste B
Nationwide Insurance: Kevin M Wiggins Agency LLC
Medicare Insurance Agent · Oswego, IL
(630) 844-1448
agency.nationwide.com/il/oswego/60543/kevin-m-wiggins-agency-llc
FI
2015 US-34 Ste M
Farmers Insurance - Carlos Correa
Medicare Insurance Agent · Oswego, IL
(630) 608-4770
agents.farmers.com/il/oswego/carlos-correa
GI
5 E Washington St
Goosehead Insurance -Petzke Agency
Medicare Insurance Agent · Oswego, IL
(331) 999-3043
UH
620 Springbrook Trail N
United Healthcare Authorized Agent
Medicare Insurance Agent · Oswego, IL
(630) 687-8727
oswegohealthplans.com

What Does a a Medicare Insurance Agent in Oswego Cost?

Medicare insurance agents in Illinois generally do not charge clients directly for their services. However, the plans they help you choose have monthly premiums that vary. For example, Medicare Part B has a standard premium of $174.70 per month in 2024. Medicare Advantage plans can have $0 premiums or higher costs depending on coverage. Medigap plans in Illinois range from about $100 to $300 per month depending on age, gender, and tobacco use. This is general information and not insurance advice. Always consult a licensed agent for your specific situation.

About medicare insurance agents in Oswego

Medicare insurance agents in Oswego, Illinois help residents navigate Medicare Part A, Part B, Part C, and Part D plans. Illinois law requires agents to be licensed by the state and follow strict marketing guidelines. Local agents understand the specific needs of Oswego seniors and can explain how Illinois Medicare Savings Programs work.

Frequently Asked Questions

When can I enroll in Medicare in Oswego, Illinois?

Your Initial Enrollment Period starts three months before you turn 65 and ends three months after your birthday month. Illinois also has a Special Enrollment Period for those who lose employer coverage. Missing these windows may result in late enrollment penalties.

What is the difference between Medicare Advantage and Medigap in Illinois?

Medicare Advantage plans (Part C) are offered by private insurers and often include drug coverage. Medigap policies help pay Original Medicare out-of-pocket costs. In Illinois, Medigap plans are guaranteed issue during your Medigap Open Enrollment Period, which lasts six months from when you turn 65 and enroll in Part B.

Do Medicare agents in Oswego charge fees for their help?

Most Medicare insurance agents in Illinois are paid by insurance companies, not by you. They typically do not charge a fee for helping you compare plans or enroll. Always confirm the agents compensation structure before working with them.

Medicare Insurance Agents in Other Illinois Cities

Listings are compiled from publicly available information. Inclusion does not constitute endorsement. Verify each medicare insurance agent's credentials and current standing with your state Department of Insurance.