Freeport, IL

At Sentry Insurance, we’re proud to call Stevens Point, Wisconsin our home. And we’re proud to extend our roots beyond Stevens Point to Freeport, Illinois.

Affectionately known as “Pretzel City, USA,” Freeport is the largest city in Stephenson County, Illinois. Freeport combines abundant natural beauty, friendly communities, great schools, abundant entertainment opportunities and a host of modern amenities. In short, the Freeport area is a wonderful place to live, work and play. With its proximity to Chicago, Madison and Milwaukee, travel to and from Freeport is quick and convenient.

To learn more about all that Freeport offers, click on the links below:

Pretzels and so much more.

A diverse and vibrant community with a rich history, Freeport combines the ideal mix of small town comforts and big city amenities, all in a convenient picturesque locale close to several of the Midwest’s most progressive cities. Freeport is “Pretzel City, USA”—a moniker hearkening back to the heritage of its Germanic settlers and the pretzel company they subsequently started.

Once you’re here, you’ll see why Freeport is so much more than just pretzels, and why it is known as one of Illinois’ most desirable communities to live, work, play, raise a family and more. From endless opportunities for year-round recreation, dining, entertainment and the arts, to great schools, affordable housing and vibrant communities—there are plenty of reasons to consider joining Sentry Insurance and making Freeport your home.

Sentry’s presence is solid and continues to grow in Freeport—our Freeport office is home to more than 100 associates. The facility itself boasts a full-service cafeteria and is equipped with all the latest in modern office technology, making it easy to work and connect with other Sentry associates across the organization. To top it off, our office is conveniently located with easy access to shopping, dining and more.

We invite you to take some time to explore all that working at Sentry and living in Freeport has to offer.

Our Location



Freeport, IL Office
1125 South Kiwanis Drive
Freeport, IL  61032
815-599-3000