Jerry works with 11 different insurance companies in the Badger State, and in the past year alone we’ve helped 6,400 Wisconsin drivers compare competitive quotes and make the switch.

Every driver’s situation is different, but because we’ve helped thousands of WI drivers like you, we know what matters most. We can show you real choices made by real people, including how other drivers in your state are picking their car insurance coverage.

Here’s what we’ve noticed:

• Progressive is the single most-chosen insurer among Jerry customers in Wisconsin.

• GEICO and Gainsco come in second and third place, with about half of the total market share.

• The rest of our customers are spread across strong carriers like Bristol West, ROOT, among others.

The takeaway is simple: there’s no one “best” company for everyone. But there is a best fit for you, based on your driving profile, coverage needs and risk tolerance.

Most popular insurers in Wisconsin

Insurer	Share of Jerry drivers	Jerry customer rating
Progressive	43%	4.7
GEICO	24%	5.0
Gainsco	9%	No Rating
Bristol West	9%	4.7
ROOT	6%	4.0

Based on the most frequently chosen carriers by Jerry customers in this state. Customer rating based on average rating by Jerry customers in this state.

Quick picks: Best Wisconsin car insurance by driver profile

Here are the categories we chose when selecting our best insurance companies for Wisconsin drivers, and why. Use this as a starting point, then let Jerry personalize the results for your exact details.

How Jerry helps Wisconsin drivers find their best insurance

Jerry is different from quote-comparison sites that just rank by price. For Wisconsin drivers, here’s what we actually do:

• Use real data from 6,400 recent Wisconsin quotes to best compare your coverage options.

• Analyze 11 top insurers against our quality criteria and your specific needs.

• Show you highly-rated options that balance coverage, claims and cost.

• Explain why each option makes sense for your situation.

• Handle all the paperwork — including cancellation and refund requests — and help you switch, so you never have a coverage gap.

• Continue monitoring market rates so you always know when it’s time to shop for better pricing.

What does that mean for WI drivers? An average annual savings of $656 and a high satisfaction rate among drivers who switch with Jerry.

You don’t need to call a dozen agents or fill out form after form, either. Just answer a few quick questions below. In minutes, Jerry will have you on the way to your best coverage and rates.

Best car insurance for most WI drivers

Wisconsin drivers have 11 insurance companies to choose from when shopping through Jerry. These carriers each bring a variety of coverages, features, benefits and prices to the table, so customers can truly shop around to find the one that offers the best balance of price and protection.

Here are some of the most recent quotes that drivers have received in the state:

Recent quotes in Wisconsin

For most drivers in Wisconsin who want full coverage and strong claims support, three companies rise to the top as customer favorites: Progressive, GEICO and Gainsco. Jerry can compare them (and more) side-by-side in just minutes, so you see which one actually works for you.

Here’s a look at what they each offer and why customers say they’re a top pick.

1. Progressive

Recent quotes for WI drivers

Based on Jerry customers with clean driving records who found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers in this state.

• Why we recommend Progressive:

  • Consistently competitive rates for a wide range of drivers.
  • Straightforward online and mobile tools for managing your policy and filing claims.
  • Flexible bundling and coverage choices for drivers who want simplicity.
  • Beyond price, Jerry customers most frequently praise Progressive for its robust app and variety of discounts.

2. GEICO

Recent quotes for WI drivers

Based on Jerry customers with clean driving records who found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers in this state.

• Why we recommend GEICO:

  • Convenient online and in-app quoting, policy updates and claims submission.
  • Competitive pricing for full coverage for a wide range of Wisconsin drivers.
  • Snapshot® can unlock extra discounts as safe driving continues.
  • Jerry customers most frequently praise GEICO for its helpful mobile app, but also enjoy this carrier’s pricing and customer service.

3. Gainsco

Recent quotes for WI drivers

Based on Jerry customers with clean driving records who found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers in this state.

• Why we recommend Gainsco:

  • Strong option for drivers rebuilding after a lapse or cancellation.
  • Flexible payment plans that make it easier to stay covered month to month.
  • Simple proof-of-insurance access for registration and day-to-day needs.
  • Jerry drivers who switched praise Gainsco for its pricing, customer service and robust mobile app.

Best WI car insurance for bundling home and auto

When you own a home, your car insurance isn’t just about dents and fender benders. It’s also there to help protect your savings and assets if you’re found responsible for an accident, as paying for someone else’s medical bills or property damage gets expensive fast.

For many homeowner drivers, bundling auto and home insurance is a simple way to keep coverage in one place and qualify for discounts that can lower your bill. But bundling isn’t the only way homeowners can benefit. Even with separate insurers, some carriers still factor in homeownership with added discounts or coverage limits that line up better with what you’re protecting.

In Wisconsin, Jerry sees most home-owning customers choosing Progressive, GEICO and Bristol West for their auto coverage, including those who do and don’t bundle those policies together. Here’s what each top carrier offers and why Jerry customers pick them most often.

1. Progressive

Recent quotes for homeowners

Based on Jerry customers with clean driving records, who own a home and found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based average rating by Jerry customers that are homeowners in the past 12 months.

• Why we recommend Progressive:

  • Robust legal and claims teams equipped for major accidents and lawsuits.
  • High liability and umbrella coverage that integrates smoothly with homeowners policies.
  • Extensive experience handling complex coverage needs for higher-asset, higher-net-worth households.
  • Beyond price, Jerry customers most frequently praise Progressive for its robust app and variety of discounts.

2. GEICO

Recent quotes for homeowners

Based on Jerry customers with clean driving records, who own a home and found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based average rating by Jerry customers that are homeowners in the past 12 months.

• Why we recommend GEICO:

  • Bundle discounts when you pair auto with home, renters or condo.
  • Highly rated app for ID cards, payments, vehicle changes and claims.
  • A++ AM Best financial strength rating for reliability.
  • Jerry customers most frequently praise GEICO for its helpful mobile app, but also enjoy this carrier’s pricing and customer service.

3. Bristol West

Recent quotes for homeowners

Based on Jerry customers with clean driving records, who own a home and found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based average rating by Jerry customers that are homeowners in the past 12 months.

• Why we recommend Bristol West:

  • Online payments and documents that keep servicing simple after purchase.
  • Farmers group backing for those who want a larger carrier infrastructure.
  • Optional towing and roadside service for day-to-day driving needs.
  • Outside of great pricing, Jerry’s Bristol West drivers particularly like the carrier’s customer service and mobile app.

Best value for budget-focused WI drivers

Budget-friendly shouldn’t mean “good luck out there.” If you want to stay under control on price but still keep real coverage in Wisconsin, you’ll usually get better results by switching carriers than by cutting limits. Our data show Progressive, GEICO and Gainsco frequently land in the sweet spot for Jerry drivers, offering strong protection for a reasonable monthly cost. The goal isn’t just the cheapest insurance in Wisconsin. It’s value: price plus protection that holds up.

Over the past 12 months, Jerry has helped 2,710 Wisconsin drivers find coverage under $100/month, without dropping to bare-minimum limits.

Here’s a look at what each top carrier offers and why Jerry customers say they’re a top pick.

1. Progressive

Recent price-friendly quotes

Based on Jerry customers with clean driving records who found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers with below-average credit profiles in the past 12 months.

• Why we recommend Progressive:

  • Budget-friendly quotes for many driver profiles, including minimum coverage shoppers.
  • Lots of discount paths like multi-car, bundling, safe driver and continuous coverage.
  • Strong self-serve experience for policy changes and claims in the app.
  • Beyond price, Jerry customers most frequently praise Progressive for its robust app and variety of discounts.

2. GEICO

Recent price-friendly quotes

Based on Jerry customers with clean driving records who found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers with below-average credit profiles in the past 12 months.

• Why we recommend GEICO:

  • DriveEasy usage-based program through the mobile app, savings potential varies by state and results.
  • Multi-vehicle and multi-policy discounts to stack savings.
  • Optional roadside assistance coverage to help manage towing and lockout costs.
  • Jerry customers most frequently praise GEICO for its helpful mobile app, but also enjoy this carrier’s pricing and customer service.

3. Gainsco

Recent price-friendly quotes

Based on Jerry customers with clean driving records who found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers with below-average credit profiles in the past 12 months.

• Why we recommend Gainsco:

  • Multiple payment methods that fit uneven income weeks.
  • Add-only-what-matters approach that avoids paying for extras.
  • Better fit for drivers who don’t qualify for clean-record pricing.
  • Jerry drivers who switched praise Gainsco for its pricing, customer service and robust mobile app.

Best car insurance for WI families with teen drivers

In Wisconsin, teen drivers are typically one of the priciest additions you can make, and the cost increase can last for years if you don’t have the right carrier and structure. The upside is that different insurers handle teen drivers very differently, so families often have room to save without cutting corners on coverage. Jerry has helped 170 WI families with teen drivers save an average of $1,051 annually, primarily with Progressive, Gainsco and Bristol West.

Here’s a look at what those top carriers offer and why Jerry customers choose them most often.

1. Progressive

Recent teen driver quotes

Based on Jerry customers with clean driving records and a teen on their policy, who found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers that have children of driving age in the past 12 months.

• Why we recommend Progressive:

  • If your policy covers multiple vehicles, a listed teen is typically covered driving any vehicle on that policy.
  • Snapshot telematics tracks factors like hard braking, rapid acceleration, time of day and miles driven.
  • Deductible Savings Bank can reduce comp or collision deductibles each claim-free policy period while enrolled.
  • Beyond price, Jerry customers most frequently praise Progressive for its robust app and variety of discounts.

2. Gainsco

Recent teen driver quotes

Based on Jerry customers with clean driving records and a teen on their policy, who found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers that have children of driving age in the past 12 months.

• Why we recommend Gainsco:

  • Useful after a cancellation or lapse when a household needs to reset fast.
  • Multiple ways to pay that work for split budgeting.
  • Simple policy structure stays manageable for busy households.
  • Jerry drivers who switched praise Gainsco for its pricing, customer service and robust mobile app.

3. Bristol West

Recent teen driver quotes

Based on Jerry customers with clean driving records and a teen on their policy, who found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers that have children of driving age in the past 12 months.

• Why we recommend Bristol West:

  • Practical option when a teen or young driver pushes pricing up sharply.
  • Payment reminders and missed-payment alerts to reduce accidental lapses in busy seasons.
  • Optional rental reimbursement keeps a household moving after a covered loss.
  • Outside of great pricing, Jerry’s Bristol West drivers particularly like the carrier’s customer service and mobile app.

Best car insurance for WI college students

College life involves a lot of things, but “predictable driving habits” usually isn’t one of them. Students may go weeks without touching the car, then suddenly drive home for a weekend or road trip out of town. That stop-start pattern can make it surprisingly easy to end up with the wrong setup or pay for coverage you don’t really need.

Jerry has helped 905 college students in Wisconsin find affordable coverage that still protects them on and off campus. Progressive, GEICO and ROOT are the most common choices for college students buying auto insurance through Jerry. Here’s why.

1. Progressive

Recent college driver quotes

Based on Jerry customers with clean driving records, between ages 17-24, who found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers that have children of driving age in the past 12 months.

• Why we recommend Progressive:

  • Distant student discount structured for students away at school without a car.
  • Tools that help limit cost spikes after a claim.
  • Discounts designed for students staying on a family policy.
  • Beyond price, Jerry customers most frequently praise Progressive for its robust app and variety of discounts.

2. GEICO

Recent college driver quotes

Based on Jerry customers with clean driving records, between ages 17-24, who found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers that have children of driving age in the past 12 months.

• Why we recommend GEICO:

  • Claim Forgiveness can be earned or purchased in many states.
  • DriveEasy Dashboard shows trips, driving stats and safety tips.
  • Good student discount for eligible full-time students.
  • Jerry customers most frequently praise GEICO for its helpful mobile app, but also enjoy this carrier’s pricing and customer service.

3. ROOT

Recent college driver quotes

Based on Jerry customers with clean driving records, between ages 17-24, who found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers that have children of driving age in the past 12 months.

• Why we recommend ROOT:

  • App-based driver testing rewards careful student drivers, versus making age-based assumptions.
  • Digital proof of insurance in-app is helpful for campus parking and registration.
  • Roadside assistance included with many policies, useful for older cars and long drives home.
  • Jerry ROOT customers primarily like the carrier’s pricing, but also praise its mobile app and customer service.

Best WI car insurance for drivers with violations

One mistake on the road can change your insurance pricing for years. Tickets, at-fault accidents and DUIs often trigger “high-risk” rates and can narrow the list of carriers willing to write your policy. Still, you have options, and you don’t have to overpay just because your record isn’t spotless.

Jerry has helped 1,162 Wisconsin drivers with violations find coverage this past year at affordable prices. We also monitor rates and flag the right time to shop again once those violations age out, so you can potentially save even more.

In fact, many Jerry drivers with violations end up with Progressive, GEICO and Gainsco — carriers that are often more flexible with Wisconsin drivers who have violations on their record.

1. Progressive

Recent quotes post-violation

Based on Jerry customers with one or more accidents and violations on their records who found savings in the past 18 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers with violations in the past 12 months.

• Why we recommend Progressive:

  • Snapshot uses recent driving behavior, not just past violations.
  • Large Accident Forgiveness available after longer tenure.
  • Non-owner SR-22 option if you need proof of insurance without a car.
  • Beyond price, Jerry customers most frequently praise Progressive for its robust app and variety of discounts.

2. GEICO

Recent quotes post-violation

Based on Jerry customers with one or more accidents and violations on their records who found savings in the past 18 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers with violations in the past 12 months.

• Why we recommend GEICO:

  • Claim Forgiveness can be added or earned in states where offered.
  • Fast self-serve access to proof of insurance and ID cards through the app or online account.
  • Support options through app, chat and phone during the policy or after a claim.
  • Jerry customers most frequently praise GEICO for its helpful mobile app, but also enjoy this carrier’s pricing and customer service.

3. Gainsco

Recent quotes post-violation

Based on Jerry customers with one or more accidents and violations on their records who found savings in the past 18 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers with violations in the past 12 months.

• Why we recommend Gainsco:

  • Available to drivers with less-than-perfect records.
  • Control costs by personalizing deductibles and limits.
  • Simple policy structure that stays easy to keep up with while rebuilding.
  • Jerry drivers who switched praise Gainsco for its pricing, customer service and robust mobile app.

Car insurance options for WI military families

For military families, driving is rarely consistent. Active-duty, reservist, guard or veteran, you might be commuting one month, storing a car the next and moving states soon after. Jerry has helped Wisconsin military families find coverage that fits deployments, PCS moves and the full stretch of military life.

If you qualify for military-focused insurers, keep them in the running. Also consider standard insurers, many offer strong military discounts and flexible policies that Jerry can quote and compare for you.

Here’s how to think about your options.

Option A: Military-only insurers to check directly

Some companies are built specifically for military members and their families. These include USAA, Navy Federal, Armed Forces Insurance and similar providers.
If you’re eligible, they at least belong on your short list. That’s because they’re designed around deployments, PCS orders and frequent moves. These insurers often have storage or reduced-use options when your car sits on base or at home during deployment. Additionally, their customer service teams understand military pay, orders and timelines in a way civilian-focused insurers sometimes don’t.

Because of how these insurers work, Jerry can’t always show live quotes or internal ratings for them. If you qualify, the smart move is to:
1. Use Jerry to see how strong your options are with standard insurers, then
2. Get a direct quote from one or more military-only insurers and compare.

That way, you’re not guessing. You’re stacking their offer against real, competitive market pricing.

Option B: Standard insurers with strong military benefits (that Jerry can quote)

Military-only providers are not the only option. Several national insurers offer military discounts, handle deployments and out-of-state moves well and are already tightly integrated with Jerry’s quote and switch flow.

For many WI military families, GEICO, State Farm and Progressive are common contenders.

1. GEICO

Best for: Deployment flexibility with strong discount potential

Why it often works well for service members:

• Military discounts plus options to adjust coverage when you deploy or drive less.

• 24/7 support that’s practical for OCONUS and rotating schedules.

• Fast app access for proof of insurance, claims and policy changes.

2. State Farm

Best for: Base-to-base moves with in-person help

Why it often works well:

• Extensive agent network that can travel with you across states.

• Strong local presence in many military communities.

• Simple bundling when you add home or condo protection.

3. Progressive

Best for: Changing routines and digital management

Why it could be a good fit:

• Competitive pricing across many profiles, including frequent movers.

• Self-serve tools to update address, mileage and garaging.

• Popular add-ons like rental and roadside for times when you’re away from home support.

Jerry can’t claim to “rank” USAA or Navy Federal against these carriers, but we can show you in minutes how GEICO, State Farm, Progressive and other standard insurers price your situation in Wisconsin.

Best car insurance for senior drivers in Wisconsin

When you’re over 65, good insurance isn’t just about the premium. It’s about trust: clear coverage, consistent rates, and support that shows up when you need it. For Wisconsin seniors, Jerry most often points to Progressive, GEICO and Bristol West because they tend to deliver that mix well.

In the last 12 months, we’ve helped 286 Wisconsin seniors find coverage that fits their driving habits today and respects their experience.

1. Progressive

Recent senior driver quotes

Based on Jerry customers 65+ with clean driving records who found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers of age 65+ in the past 12 months.

• Why we recommend Progressive:

  • Snapshot telematics base price on hard braking, rapid acceleration, time of day, miles driven and phone use.
  • Pet injury coverage included with collision coverage, for up to $1,000 in vet bills after an accident.
  • Small Accident Forgiveness for a first claim up to $500 in most states.
  • Beyond price, Jerry customers most frequently praise Progressive for its robust app and variety of discounts.

2. GEICO

Recent senior driver quotes

Based on Jerry customers 65+ with clean driving records who found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers of age 65+ in the past 12 months.

• Why we recommend GEICO:

  • DriveEasy telematics reward safer habits and lower-risk driving.
  • Paid-in-full, autopay and paperless discounts can help reduce your total bill.
  • Mechanical Breakdown Insurance option for newer cars, eligibility rules apply.
  • Jerry customers most frequently praise GEICO for its helpful mobile app, but also enjoy this carrier’s pricing and customer service.

3. Bristol West

Recent senior driver quotes

Based on Jerry customers 65+ with clean driving records who found savings in the past 12 months. Savings depend on coverage and other factors. Potential savings will vary.

Customer rating based on average rating by Jerry customers of age 65+ in the past 12 months.

• Why we recommend Bristol West:

  • Easy to make policy and coverage changes directly when drivers’ needs change.
  • Billing flexibility for fixed-income planning.
  • Rental reimbursement options after a covered loss.
  • Outside of great pricing, Jerry’s Bristol West drivers particularly like the carrier’s customer service and mobile app.

How Jerry picks the best insurers in Wisconsin

Most sites just sort companies by price. Jerry does more. 

No one wants to overpay for insurance, but Jerry knows that other factors matter, too. We use our own proprietary Jerry Score to grade each insurance company. Built from real Wisconsin driver data, this score evaluates insurers on:

What does all of this mean for you? Jerry options are tailored to how you actually drive and what you own, so you can make the best possible and most informed decision when shopping for coverage in Wisconsin.