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Find Medicare Insurance Agents Near You in Chesterton, IN

Browse medicare insurance agents serving Chesterton, Indiana. Contact information and addresses listed below.

18 agents listed
Updated May 2026
Chesterton, IN
Important: Listings are compiled from publicly available sources and have not been independently verified by BeforeInsuranceUSA.com. We do not endorse any agent or guarantee outcomes. Verify licensing and disciplinary status with the Department of Insurance of Indiana before hiring.
Showing 18 medicare insurance agents in Chesterton, IN Listings are displayed in no particular order and are not ranked by BeforeInsuranceUSA. Order does not constitute a recommendation or endorsement of any agent.
Joshua Baumgartner - State Farm Insurance Agent
218 S Calumet Rd, Chesterton, IN 46304
(219) 728-6959 indianasfjosh.com
Thomas Wisch: Allstate Insurance
711 Plaza Dr Ste 1, Chesterton, IN 46304
(219) 224-3244 agents.allstate.com
South Shore Insurance
760 S Calumet Rd, Chesterton, IN 46304
(219) 395-1747 southshoreins.net
Jim Wells - State Farm Insurance Agent
422 Broadway Ave, Chesterton, IN 46304
(219) 926-7506 statefarm.com
Shepherd Insurance
155 S Calumet Rd, Chesterton, IN 46304
(219) 926-8681 shepherdins.com
Cuna Mutual Group
515 Broadway Ave # A, Chesterton, IN 46304
(219) 600-5435
Pat Hudson - State Farm Insurance Agent
226 N Calumet Rd, Chesterton, IN 46304
(219) 926-5377 insurewithpathudson.com
AAA Insurance - Tom Little Insurance Agency
802 Wabash Ave Ste. 110, Chesterton, IN 46304
(219) 250-2841 locator.acg.aaa.com
Chris Nielsen - State Farm Insurance Agent
751 E Porter Ave #4, Chesterton, IN 46304
(219) 926-7700 chestertonagent.com
Jim Kristoff - State Farm Insurance Agent
536 Indian Boundary Rd, Chesterton, IN 46304
(219) 926-7649 myagentjimkristoff.com
Justin Salamanca Agency, LLC American Family Insurance
103 W Morgan Ave, Chesterton, IN 46304
(219) 510-5405 amfam.com
Heritage Advisory Group
1496 Pope Ct # 1, Chesterton, IN 46304
(219) 926-4400 heritagegroup.info
Indiana Senior Advisors
1050 Broadway Ave Ste 22, Chesterton, IN 46304
(219) 250-5445 indianasenioradvisor.com
Progress Insurance Co.
560-580 Indian Boundary Rd, Chesterton, IN 46304
(509) 790-6498 paulenedraughon089.wixsite.com
Mature Market Insurance Services, LLC
209 S Calumet Rd #7, Chesterton, IN 46304
(219) 395-9124 maturemarketinsurance.com
Allstate Personal Financial Representative: Jeffrey Huffman
711 Plaza Dr Ste 1, Chesterton, IN 46304
(219) 224-3244 agents.allstate.com
AnchorPoint Insurance Solutions
425 Sand Creek Dr N, Chesterton, IN 46304
(219) 338-2090 anchorpointins.com
Kyle Legler - Indiana Farm Bureau Insurance
402 Indian Boundary Rd, Chesterton, IN 46304
(219) 926-1004 infarmbureau.com

What Does a Medicare Insurance Agent in Chesterton Cost?

Medicare insurance agents in Indiana do not charge you directly for their services; they receive commissions from insurance carriers. Plan premiums vary widely: Medicare Advantage plans in Porter County can have $0 monthly premiums, while Medigap plans typically range from $100 to $300 per month depending on your age and health status. Part D prescription drug plans average about $30 to $70 per month in Indiana. This is general information and not insurance advice.

* Cost estimates are general ranges based on publicly available data and compiled using automated research tools. Actual fees vary by agent and case complexity. This is not insurance advice — consult directly with an agent for fee specifics.

Frequently Asked Questions

What does a Medicare insurance agent in Chesterton do?
A Medicare insurance agent in Chesterton helps you compare plans explain coverage details and assist with enrollment. They are licensed by the state of Indiana and can represent multiple insurance carriers. They do not provide legal advice but can answer questions about plan benefits.
When can I enroll in Medicare in Indiana?
Your Initial Enrollment Period starts three months before your 65th birthday and ends three months after. Indiana also has an Annual Enrollment Period from October 15 to December 7 each year. Special Enrollment Periods may apply if you lose other coverage or move.