Family-owned in Illinois & Wisconsin since 2009 Same-day quotes · we shop 14 carriers for you After-hours claims? Mary & Jim are always on-call 4.9 / 5 from 420+ neighbors · bundled discounts up to 28%
(815) 555-0199
C Calderwood Insurance Agency · Est. 2009
Husband & wife · Independent agency

Insurance that
remembers your name

For 16 years, the Calderwood family has helped neighbors across Illinois and Wisconsin protect what matters — homes, cars, businesses, and the people inside them. No phone trees. No surprise renewals. Just two agents who answer the phone.

Call (815) 555-0199 Get a 60-second quote
M
J
+
4.9 / 5
from 420+ client reviews
Family insurance agency office welcoming clients
Midwestern family home with welcoming front porch
Insurance agent handshake with client, trust and welcome
Happy family outdoors enjoying time together
Carriers we shop for you Progressive Travelers Nationwide Safeco Foremost Encompass
+
Years protecting families
+
Policies in force
/5
Avg. client rating
m
Avg. call-back time
What we cover

Coverage built around the life you've built.

We don't sell off a list. We sit with you, hear what matters, then quote you across 14 carriers so the policy actually fits.

Family sedan in driveway, auto insurance
Auto

Auto insurance

Liability, collision, gap, accident forgiveness, and discounts for multi-car, students, and clean drivers — bundled where it pays.

From $58/mo Quote auto
Welcoming midwestern home with porch
Home

Homeowners & condo

Dwelling, contents, liability, sewer back-up, and replacement cost — annual reviews so coverage scales with your renovations.

From $72/mo Quote home
Parents and child at home, life insurance
Life

Life & final expense

Term, whole, and indexed universal. We model 10/20/30-year scenarios so you see the numbers, not a sales pitch.

From $24/mo Quote life
Small business owner at workshop counter
Business

Business & BOP

General liability, workers' comp, commercial auto, and cyber — packaged for trades, retail, and professional services.

Custom quote Quote business
Young couple unpacking boxes, renters insurance
Renters

Renters insurance

Contents, liability, and loss-of-use for apartments, townhomes, and rentals — usually under a buck a day.

From $14/mo Quote renters
Motorcycle and boat on lakeshore, specialty insurance
Specialty

Boat, RV & motorcycle

Toys deserve protection too. Coverage for boats, RVs, motorcycles, ATVs, and the trailers that haul them.

Seasonal options Quote specialty
Family-owned✦ Independent & un-captive✦ Same-day quotes✦ 14 carriers shopped✦ Real humans answer✦ Annual coverage reviews✦ Bundle & save✦
Auto·Home·Life·Business·Renters·Boat·RV·Motorcycle·
Mary and Jim Calderwood, husband-and-wife insurance agents
Our family

Calderwood is two agents who picked up the phone when nobody else would.

Jim left a captive carrier in 2009 because he was tired of selling the same policy to families it didn't fit. Mary joined a year later. Today we're still just the two of us — plus a part-time service rep who's been with us since the beginning — quietly insuring 1,400 households across Illinois and Wisconsin.

  • You always reach a person.
    No phone trees. No outsourced call center. Jim or Mary picks up.
  • We shop 14 carriers, not one.
    Independent means we work for you, not a single insurer.
  • Annual coverage reviews.
    We re-shop your policies every renewal — savings, not surprises.
Meet the Calderwoods How we work
Where we serve

Two states. Forty-three communities.

Wherever the back roads take us, we're licensed to follow.

Illinois rural countryside and small-town communities
Illinois
Northern Illinois & the Rock River corridor
Rockford · Rockton · Roscoe · Loves Park · Belvidere · Freeport · Aurora · Naperville · +18 more
3,100+ policies in-state
Wisconsin lakes, woods and small-town communities
Wisconsin
Southern Wisconsin & the Lake Country
Beloit · Janesville · Madison · Kenosha · Racine · Lake Geneva · Milton · Delavan · +14 more
1,100+ policies in-state

Not sure if you're in our service area? Call us — we'll know in 10 seconds.

How it works

Three steps. Most clients are covered the same day.

1

Tell us about your life.

Call, text, or fill the form. We listen first, ask the right questions, and learn what you actually need to cover.

2

We shop 14 carriers.

Within hours, you get a side-by-side comparison — coverage limits, deductibles, premiums, all in plain English.

3

You're covered today.

Sign electronically, and your policy is active before dinner. We handle every renewal and claim from there on.

Real life

The moments we're quietly protecting.

First homes. Family road trips. Saturday garages. The everyday stuff worth insuring.

Family in golden hour outdoors
Family
Saturday afternoons.
Family insurance agency at work
Office
204 N. Main.
Lake cabin summer getaway
Summer
Lake country.
American midwestern porch home
Home
The porch light.
Insurance agent and client meeting
Trust
A handshake.
Client stories

Sixteen years. A few thousand neighbors.

"Tree fell on the house at 11pm in a windstorm. Mary picked up at 11:04pm. We had an adjuster on-site the next morning."

D
Diane K.
Homeowner · Rockford, IL

"Jim re-shopped our business policy and dropped the premium by $4,200 a year. Same coverage. Better carrier."

R
Ryan T.
Owner, Lakeside HVAC · Madison, WI

"Our previous agent retired. Calderwood reviewed everything we had and found two gaps the old policy never covered."

S
Sarah M.
Family of four · Kenosha, WI

"First-time homebuyers. Jim spent an hour walking us through every line. Felt like he was protecting his own kids."

A
Anthony & Beth P.
First-time buyers · Naperville, IL

"Mary remembered my daughter's name on a follow-up call months later. That's how you know it's a family business."

M
Marcus G.
Auto + life policy · Aurora, IL
Free comparison

See your policy shopped across 14 carriers — in under 60 seconds.

No obligation. No spam. Just an honest side-by-side from two agents who've been doing this for sixteen years.

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