($850) Cost to ship a car from Chesapeake, VA to Milwaukee, WI

Quick answer: On average, moving a car 986 miles from Chesapeake, Virginia, to Milwaukee, Wisconsin, will run you about $850 to $1,306. Prices shift based on factors such as the vehicle’s size, the transport option you choose, and the time of year. Get a tailored estimate with our car shipping cost calculator.

moveBuddha logo iconrating starstarstarstarstar 4.7 / 5
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  • Refundable deposit
  • Discounts available
moveBuddha logo iconrating starstarstarstarstar 4.5 / 5
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  • Price lock promise
  • Free car wash
moveBuddha logo iconrating starstarstarstarstar 4.5 / 5
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  • Door-to-door service
  • No upfront payment

Shipping a car the reverse route? We've got you covered with our Milwaukee to Chesapeake car shipping guide.

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Recommended by Time Magazine
Recommended by The New York Times
Recommended by Forbes
Recommended by Money.com
Recommended by Consumer Reports

Each year, 400,000+ people trust our car shipping recommendations. Here are a few reasons why:

  • Founded in 2015
  • 2,500+ car shipping companies analyzed
  • $50,000 in moving & auto transport grants delivered
  • Up-to-date pricing info & industry data
  • Fact-checked for accuracy

The best Chesapeake to Milwaukee car shipping companies

Based on our research, here are the best car shipping companies for getting your car from Chesapeake to Milwaukee:

Best for Real-Time Tracking
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moveBuddha logo iconrating starstarstarstarstar 4.7 / 5
Get a quote (224) 310-1412
At A Glance
  • GPS tracking
  • Instant online quotes
  • Economy option
  • Ships nationwide
  • Easy online scheduling
read our full review
Get a quote (224) 310-1412
Best for accurate pricing
Licensedcheckmark
Insuredcheckmark
Price dollar sign dollar sign dollar sign dollar sign
moveBuddha logo iconrating starstarstarstarstar 4.5 / 5
Get a quote (833) 775-1461
At A Glance
  • Price Lock Promise
  • Pay by credit card
  • Free car wash at delivery
  • No upfront deposit
  • Door-to-door service
read our full review
Get a quote (833) 775-1461
Best for safety & reliability
Licensedcheckmark
Insuredcheckmark
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moveBuddha logo iconrating starstarstarstarstar 4.5 / 5
Get a quote 224-206-5633
At A Glance
  • Competitive pricing & $0 upfront
  • GPS tracking
  • Multiple insurance options
  • Guaranteed pickup dates available
  • Door-to-door service
read our full review
Get a quote 224-206-5633
Best for overall value
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moveBuddha logo iconrating starstarstarstarstar 4.9 / 5
Get a quote (864) 492-1221
At A Glance
  • No hidden fees
  • Free online quotes
  • Door-to-door service in 48 states
  • Exact pickup dates
  • Ships to & from HI
read our full review
Get a quote (864) 492-1221

Top local car shippers in Chesapeake

If sticking with a local company is important to you, here are the top car shipping companies based in Chesapeake, VA:

  1. Ship A Car ASAP: 3.72 out of 5 stars
  2. Safemile Auto Transport: 3.66 out of 5 stars
  3. Speedy Car Shipping Norfolk: 3.56 out of 5 stars
  4. Virginia Beach Auto Transport: 3.5 out of 5 stars
  5. Xpress Auto Transport: 3.5 out of 5 stars

Ship A Car ASAP

4801 Glenwood Ave Suite 200, Raleigh, NC 27612 US

starstarstarstarstar3.72 / 5.0

Customers consistently praise David’s exemplary service, highlighting his professionalism, excellent communication, and the efficiency of the car shipping process. However, some feedback indicates occasional delays in response times from representatives at the company.

Get a Quote (844) 321-2727

Services Offered

  • Open transport
  • Enclosed transport
  • Interstate shipping
  • Insured shipping
  • Expedited delivery
  • Multi-car transport
  • Classic cars
  • RVs
  • ATVs
  • Trailers
  • Motorcycles
  • Heavy equipment
  • Boats
  • Electric vehicles
  • Inoperable cars

Additional Information

Alternative Business Names

  • JE Carriers, LLC

Safemile Auto Transport

500 E Main St 16th floor, Norfolk, VA 23510 US

starstarstarstarstar3.66 / 5.0

Customers frequently commend Safemile for their excellent communication, professional service, and timely deliveries. However, some express initial anxiety about trust in the shipping process before experiencing the service firsthand.

Get a Quote (888) 277-8212

Services Offered

  • Open transport
  • Enclosed transport
  • Interstate shipping
  • Insured shipping
  • Shipment tracking
  • Expedited delivery
  • Multi-car transport
  • Classic cars
  • ATVs
  • Motorcycles
  • Heavy equipment
  • Boats
  • Electric vehicles
  • Inoperable cars

Discounts

  • Military
  • Senior

Additional Information

Speedy Car Shipping Norfolk

2607 Wyoming Ave, Norfolk, VA 23513 US

starstarstarstarstar3.56 / 5.0
Get a Quote (757) 654-4855

Services Offered

  • Open transport
  • Enclosed transport
  • Interstate shipping
  • International shipping
  • Insured shipping
  • Expedited delivery
  • Multi-car transport
  • Classic cars
  • ATVs
  • Motorcycles
  • Boats
  • Electric vehicles
  • Inoperable cars

Discounts

  • Military
  • Senior

Additional Information

Virginia Beach Auto Transport

3269 Dam Neck Rd, Virginia Beach, VA 23453 US

starstarstarstarstar3.5 / 5.0

Customers praised the punctuality and honesty of the drivers, while expressing significant concerns about service reliability and accusations of fraudulent practices.

Get a Quote (757) 366-2142

Services Offered

  • Open transport
  • Enclosed transport
  • Interstate shipping
  • Insured shipping
  • Expedited delivery
  • Classic cars
  • Motorcycles
  • Heavy equipment
  • Boats

Additional Information

  • Pay by cash
  • Deposit Required

Xpress Auto Transport

4519 Bainbridge Blvd #340, Chesapeake, VA 23320 US

starstarstarstarstar3.5 / 5.0
Get a Quote (866) 333-5509

Services Offered

  • Open transport
  • Enclosed transport
  • Interstate shipping
  • International shipping
  • Insured shipping
  • Shipment tracking
  • Expedited delivery
  • Multi-car transport
  • Classic cars
  • RVs
  • Trailers
  • Motorcycles
  • Heavy equipment
  • Boats
  • Electric vehicles
  • Inoperable cars

Additional Information

How we chose the best car shipping companies

We analyzed 2,400 car shipping companies nationally and evaluated and rated them based on key factors using our unique system of methodology.

Here’s what we considered:

  • Standard services: We looked at the types and variety of services each company provides. This includes whether they offer open transport, enclosed transport, or both. We also rated companies based on whether they have door-to-door shipping or just terminal pickup and delivery and the kinds of vehicles they ship. Companies that move RVs, motorcycles, and other specialty vehicles scored higher than those that just ship cars.
  • Add-on services: We gave additional points to companies that provide special optional services like expedited shipping, guaranteed pickup times, car washes, and rental car reimbursement.
  • Customer satisfaction: We analyzed consumer reviews on multiple major platforms, such as Yelp, Google, and Trustpilot to see whether a car shipping company delivers services promptly with good communication and within the estimated cost. We also evaluated each company’s standing within the car shipping industry as a whole by confirming U.S. Department of Transportation (USDOT) licensure and checked their membership in — and reputation with — trade associations.
  • Availability: We awarded points to each company based on their service areas. Companies that are available in Alaska and Hawaii, in addition to the continental U.S., scored higher than those that just service the Lower 48 or fewer states.
  • Scheduling and payment: We reviewed the ease with which customers can schedule services and estimate their costs through accurate quotes, price matching, flat-rate pricing, and other perks. Car shippers that give binding quotes or a price-lock promise got more positive rankings than those that are not as transparent with pricing.

Car shipping alternatives from VA to WI

When you’re moving from Chesapeake to Milwaukee, there are several ways to get your car to your new home. Here are the most common car shipping alternatives. Each one has its own benefits and trade-offs.

Coordinate with your movers

When relocating from Chesapeake to Milwaukee, most of the top-rated moving companies can bundle auto transport into your move by partnering with national car shippers. The trade-off is convenience versus flexibility, since you’ll be tied to their carrier of choice and rates.

Drive your car

When deciding whether to drive your car or ship it, it’s important to weigh both sides. Driving the 986 miles from Chesapeake to Milwaukee can save money and even turn into a memorable trip. On the flip side, the extra miles mean more vehicle wear and the chance of running into bad weather or hazards on the road.

Use a driving service

Another possibility is paying someone to drive your car from Virginia to Wisconsin. While convenient, it can be costly, and you’ll want to thoroughly vet the driver before handing over your keys in Chesapeake. No matter who drives, your car will still rack up extra miles on the way to Milwaukee.

Ship your car via train

Rail shipping offers a cost-effective and secure way to move your car to Milwaukee, and it’s particularly practical if your household items are also traveling by train. In fact, it’s the cheapest shipping option for vehicles. Just be aware that this approach has limited service locations and takes more time than other transport methods.

Factors affecting Chesapeake to Milwaukee car shipping costs

When transporting your vehicle from Chesapeake to Milwaukee, these factors will influence the cost:

Transport method

You have a few different options for shipping your car from Chesapeake to Milwaukee, including open, enclosed, and top-loaded transport. The method you should choose depends on your specific needs.

Open carriers are the most cost-effective option, while enclosed transport provides added protection for luxury or classic cars. If you’re uncertain which option to use to get your vehicle to Milwaukee, refer to our guide on comparing open vs. enclosed car shipping.

Vehicle size and type

Vehicle size plays a major role in determining your shipping costs from Chesapeake. Larger models add both bulk and weight to the trailer, raising the overall expense. So, moving a full-size SUV to Milwaukee will be more expensive than shipping a compact vehicle.

Distance and route

Simply put, the farther you ship your car, the more it will cost. Longer trips mean higher fuel and labor costs, plus added expenses like tolls and carrier maintenance. For example, transporting your vehicle 986 miles from Chesapeake to Milwaukee will cost more than a shorter move within Virginia.

Your destination plays a role as well. Routes that follow major highways are usually cheaper, while deliveries to remote areas tend to be more expensive.

The time of the year

Seasonal demand and weather conditions in both Chesapeake and Milwaukee can impact car shipping prices.

It is advisable tp plan your relocation to Chesapeake on May, October and September are the most pleasant months in Chesapeake, while July and January are the least comfortable months.

Milwaukee's location in the Great Lakes Region often has rapidly changing weather, producing a humid continental climate, with cold, snowy winters, and hot, humid summers. Thunderstorms in the region can be dangerous and damaging, bringing hail and high winds. In rare instances, they can bring a tornado. Be sure to check your weather app to avoid inclement weather during your move.

During peak moving times like summer and the winter holidays, demand for car shipping services increases, leading to higher prices. Shipping your car from Chesapeake to Milwaukee during these peak seasons can result in higher costs.

Fuel prices

Fuel price fluctuations can greatly influence transport costs. This is a critical factor given the 986-mile distance between Chesapeake and Milwaukee and the varying fuel prices across different regions. When fuel prices are high, shipping costs will rise accordingly.

Delivery expectations

Some carriers provide shipping discounts if you’re flexible on delivery dates. The average transport time from Chesapeake to Milwaukee is two to seven days. Being flexible can cut costs, but expedited options guarantee faster delivery at a premium.

Comparing Chesapeake and Milwaukee vehicle regulations

Parking permits

  • Chesapeake:
  • Milwaukee: For the convenience of the city’s night parking permit customers, there is no longer a requirement to display a physical permit. Now, when residents buy a night parking permit, they will complete the same application and receive a confirmation number to prove purchase of the permit, but will not receive a physical permit to place on the vehicle’s window. The license plate number will be used by parking enforcement to determine whether the owner has purchased a valid permit. All customer service problems arising from misplaced or stolen permits will be eliminated. A night parking permit currently costs $20 per 4-month trimester or $40 for the calendar year. Failure to purchase a permit will still be subject to a $20 citation. Permits may be purchased online. Visit www.milwaukee.gov/parking for more information and call 414-286-CITY (2489) with any questions.

Car insurance requirements

  • Chesapeake: It's crucial for drivers to have liability insurance, meeting the state's minimum coverage requirements: $25,000 for individual injury or death, $50,000 for injury or death involving multiple individuals, and $20,000 for property damage. Elevate your road safety with mandatory uninsured motorist coverage, ensuring protection with matching limits. Stay road-ready by fulfilling these insurance obligations in Virginia.
  • Milwaukee: Wisconsin requires auto insurance policies to provide a minimum coverage of $10,000 for property damage, $25,000 for individual injury or death, and $50,000 for injury or death involving multiple individuals.

Vehicle inspections

  • Chesapeake: All vehicles must pass annual safety and emissions inspections at DMV-approved stations. Vehicles that fail can be re-inspected for free within 60 days. Upon passing, a sticker is issued to indicate the vehicle's compliance.
  • Milwaukee: Safety and emission inspections are not required in Wisconsin. However, you must take your vehicle for emissions inspection available at select privately owned businesses including vehicle repair facilities, service stations, and car dealerships.

Driver’s license

  • Chesapeake: To obtain a driver's license, individuals must pass written, vision, and driving tests. To be eligible, individuals must be at least 16 years old and have held a learner's permit for at least 9 months. Specialized license types such as motorcycle, commercial, and provisional for under 18 are also available. Drivers with a valid out-of-state license can convert it without taking the test. Driver's licenses are issued by the DMV and are valid for 8 years, and can be renewed online or in person.
  • Milwaukee: After establishing residence, new residents must apply for a WI driver license at any Wisconsin DMV service center within 60 days for a regular license and within 30 days for a Commercial Driver License (CDL).

FAQ

How much does it cost to ship a car from Chesapeake to Milwaukee?

The cost to ship a car from Chesapeake, VA to Milwaukee, WI varies based on several factors, including the type of transport (open vs. enclosed car shipping), vehicle size and weight, and the current fuel prices. On average, transporting your vehicle from Chesapeake to Milwaukee will range from $850 to $1,306.

How long will it take to ship my car from Chesapeake to Milwaukee?

It will take approximately two to seven days to ship your car the 986 miles from Chesapeake to Milwaukee. If you need it quicker, ask your shipper about expedited delivery.

What’s the cheapest way to ship my car from Chesapeake to Milwaukee?

An open-transport car carrier is the cheapest way to ship your car from Chesapeake to Milwaukee. However, there are other methods. Read our post on the cheapest way to ship a car to learn more.

Is it cheaper to ship my car or drive it from Chesapeake to Milwaukee?

It is generally cheaper to drive your car from Chesapeake to Milwaukee than to ship it. However, when deciding whether to drive your car or ship it, you need to factor in related costs like maintenance fees that could result from the additional wear-and-tear on your vehicle during the 986-mile trip. Long-distance trips also involve food and possibly lodging, which can add up quickly.

We recommend that you reach out to at least a few of the top car shippers to ask about seasonal rates and auto transport discounts. You can also use our car shipping calculator to quickly generate and compare quotes from multiple companies.

Helpful Chesapeake resources