Best Chesapeake to Milwaukee Movers + Moving Guide
Want help with the heavy lifting?
If you're moving from Chesapeake to Milwaukee and need first-hand information you can trust to make this 995 mile move from Virginia to Wisconsin go smoothly, Great Guys Moving is here to help. We've analyzed 24 Chesapeake to Milwaukee moving companies and more than 20,000 movers nationwide to provide up-to-date and data-driven information about: which moving company to hire (our top recommendation is About Time Moving Systems LLC), how much the move costs (approximately $2,000 - $6,500 depending on how much stuff you have), and what it will be like living in Chesapeake compared to Milwaukee. With a move this big, you want big data on your side and Great Guys Moving is your trusted ally to help you sift through the noise to make informed moving decisions.

Best Chesapeake to Milwaukee Moving Companies
Rank | Company Name | Rating | Affordability Index | License | Contact |
---|---|---|---|---|---|
1 | About Time Moving Systems LLC | 9.32 | 9.33 | Authorized For HHG | Contact |
2 | Gorilla Movers Of Wisconsin Inc. | 9.30 | 9.31 | Authorized For Property, HHG | Contact |
3 | Marathon Moving Services | 9.27 | 9.25 | Authorized For HHG | Contact |
4 | Prime Movers USA | 9.07 | 9.39 | Authorized For Property, HHG | Contact |
5 | A Friendly & Affordable Mover | 8.22 | 8.74 | Authorized For Property, HHG | Contact |
Cost to Move from Chesapeake to Milwaukee
Moving a 1 bedroom apartment 995 miles from Chesapeake, VA to Milwaukee, WI will cost on average $2,627 to hire full service movers. A 3 bedroom Chesapeake to Milwaukee move is roughly $6,312. See the chart below for a detailed breakdown by type of move and home size. Pricing will vary based upon the exact locations of pickup and dropoff as well as several other factors. The most important pricing component that is often overlooked is how far away the move date is. The earlier you can reserve movers, the better your pricing and options will be.
Home Size | Moving Cost | Volume of Packed Items (ft³) | $/ft³ |
---|---|---|---|
Studio | $1,767 | 300 ft³ | 5.89 |
1 Bedroom | $2,627 | 450 ft³ | 5.84 |
2 Bedrooms | $4,341 | 750 ft³ | 5.79 |
3 Bedrooms | $6,312 | 1100 ft³ | 5.74 |
4 Bedrooms | $9,102 | 1600 ft³ | 5.69 |
5+ Bedrooms | $10,149 | 1800 ft³ | 5.64 |


Moving in the opposite direction? Here is our moving from Milwaukee to Chesapeake guide.
Compare the 5 Best Chesapeake to Milwaukee Movers
These are the top recommended movers based on our unbiased & regularly updated ranking algorithm (NOT paid promotions)

About Time Moving Systems LLC
4909 8th Ave
Kenosha, WI, 53140
About About Time Moving Systems LLC
This locally owned and operated moving company serves the Milwaukee, WI, area with high-quality residential and commercial relocation services. About Time...
Services
- Local moving
- Long-distance moving
- Cross-country moving
Interstate Moving License
USDOT / MC Status Entity Type | 2525330 / 877057 Authorized For HHG Carrier |
Registered Trucks/Vans | 4 |
Registered Drivers | 2 |
Total Annual Miles Moved | 50,000 (2022) |

Gorilla Movers Of Wisconsin Inc.
310 Progress Way Suite 140
Sun Prairie, WI, 53590
About Gorilla Movers Of Wisconsin Inc.
As a locally owned and operated moving company, Gorilla Movers has over 20 years of experience performing high-quality residential and commercial...
Services
- Residential moves
- Commercial moves
- Local/statewide moving
Interstate Moving License
USDOT / MC Status Entity Type | 2627768 / 1031866 Authorized For Property, HHG Carrier |
Registered Trucks/Vans | 7 |
Registered Drivers | 14 |
Total Annual Miles Moved | 173,000 (2023) |

Marathon Moving Services

MMS
Virginia Beach, VA, 23464
About Marathon Moving Services
Are you looking for an independently-owned moving company that provides affordable and reliable moving services in Virginia Beach? Marathon Moving Services...
Services
- Residential Moves
- Commercial Moves
- Packing & Delivery
Interstate Moving License
USDOT / MC Status Entity Type | 3572153 / 1552140 Authorized For HHG Carrier |
Registered Trucks/Vans | 3 |
Registered Drivers | 8 |
Total Annual Miles Moved | 20,000 (2023) |

Prime Movers USA
531 Fountain Lake Dr
Virginia Beach, VA, 23451
About Prime Movers USA
Based in Virginia Beach, VA, Prime Movers offers premium moving services at unmatched prices. Founded in 2015, it takes pride in...
Services
- Local moves (within 50 miles)
- Long distance moves (over 50 miles)
- Packing/unpacking services
Interstate Moving License
USDOT / MC Status Entity Type | 2995403 / 21183 Authorized For Property, HHG Carrier |
Registered Trucks/Vans | 2 |
Registered Drivers | 2 |
Total Annual Miles Moved | 9,060 (2023) |

A Friendly & Affordable Mover

516 Central Dr Suite 104
Virginia Beach, VA, 23454
About A Friendly & Affordable Mover
A Friendly and Affordable Mover is a locally-owned moving company in Virginia Beach, VA. Founded in 1989, this company is one...
Services
- Local and long-distance professional moving services
- Free in-home estimates
- Loading and unloading services for rental trucks, storage areas, and PODS
Interstate Moving License
USDOT / MC Status Entity Type | 3239170 / 1036449 Authorized For Property, HHG Carrier |
Registered Trucks/Vans | 2 |
Registered Drivers | 4 |
Total Annual Miles Moved | 60,000 (2022) |

Dependable Rankings You Can Count On!
Our rankings are data-driven — movers cannot purchase a spot on our list. Here's why you can have confidence in our recommendations:
- No Paid Placements: Every company earns its spot through merit, not payment.
- Extensive Analysis: Evaluated over 24,000 movers across the country for our rankings.

Dependable Rankings You Can Count On!
Our rankings are data-driven — movers cannot purchase a spot on our list. Here's why you can have confidence in our recommendations:
- No Paid Placements: Every company earns its spot through merit, not payment.
- Extensive Analysis: Evaluated over 24,000 movers across the country for our rankings.
Chesapeake vs. Milwaukee Neighborhood Comparison
Moving to a new city can be daunting, especially when trying to find a neighborhood that feels like home. We make this easier by comparing local neighborhoods between Chesapeake, VA & Milwaukee, WI . By identifying comparable neighborhoods in Milwaukee to those in Chesapeake, we aim to help you find a new area that matches your lifestyle and preferences seamlessly.
Chesapeake | Milwaukee | How They're Similar |
---|---|---|
Great Bridge | Bay View | Vibrant, family-friendly vibe |
Greenbrier | Wauwatosa | Mix of residential & commercial |
Deep Creek | Riverwest | Diverse, with a strong sense of community |
Hickory | Shorewood | Quiet, affluent area with excellent schools |
Western Branch | West Allis | Suburban feel with ample amenities |
Indian River | Walker’s Point | Historic with a modern twist |
South Norfolk | Brewer's Hill | Rich history and diverse culture |
Grassfield | Brookfield | Family-oriented, spacious parks |
Great Bridge East | Third Ward | Trendy, upscale living |
Edinburgh | East Side | Youthful energy, vibrant nightlife |
For those moving from Chesapeake's Great Bridge to Milwaukee, Bay View offers a similarly vibrant and family-friendly atmosphere, with local eateries and parks lining the streets. If you appreciate the blend of residential and commercial spaces in Greenbrier, Wauwatosa is an excellent Milwaukee counterpart, known for its unique blend of charming homes and bustling shopping districts like the Village of Wauwatosa. Hickory residents will find Shorewood's quiet, affluent neighborhoods ideal, boasting top-rated schools and a strong community feel. Moreover, Indian River's unique blend of history and modern conveniences mirrors what you'll discover in Walker’s Point, where historical buildings have been revitalized into contemporary lofts, restaurants, and shops. Lastly, Chesapeake's Edinburgh parallels Milwaukee's East Side in offering a youthful energy and vibrant nightlife, along with a diverse array of dining, entertainment, and outdoor activities.
Ready to start your move?
Pros and Cons of Moving from Chesapeake to Milwaukee
Moving from one city to another offers a chance to weigh the cons of living in Chesapeake, VA against the pros of embracing Milwaukee, WI. This comparison aims to provide an honest reflection on the significant changes you can expect, highlighting both the challenges and the rewards that this transition might bring.
- Higher humidity
- Less cultural diversity
- Fewer museums
- Smaller city vibe
- Seasonal weather
- Rich cultural diversity
- More museums
- Larger urban feel
- Colder winters
- No beach access
- Higher cost of living
- More urban areas
- Warmer winters
- Beach access
- Lower cost of living
- More suburban areas
Moving from Chesapeake to Milwaukee introduces you to a new cultural landscape. Milwaukee's vibrant arts scene is highlighted by institutions like the Milwaukee Art Museum and the Pabst Theater, offering a rich tapestry of history and creativity compared to the fewer museums in Chesapeake. The city's diverse culinary scene, with local gems such as Mader's Restaurant known for its German cuisine, and Lakefront Brewery for craft beer enthusiasts, provides a flavorful exploration not as readily found back in Virginia. Milwaukee's celebrated seasonal festivals, like the Summerfest, the world's largest music festival, offer unique experiences that mirror the city's cultural diversity and community spirit, welcoming newcomers with open arms.
Chesapeake vs. Milwaukee Food Guide
This is a comparison of the local cuisine between Chesapeake & Milwaukee, demonstrating how food is an essential element of local culture and the overall living experience in an area. By comparing these two locations, you'll be better acquainted with the culinary scene of your new home.
Chesapeake | Milwaukee | |
---|---|---|
Most iconic local food item | Chesapeake Blue Crab | Beer Brats |
Most popular meat dish | Virginia Ham | Polish Sausage |
Most popular street food item | Oyster Po' Boy | Fried Cheese Curds |
Most popular vegan food | BBQ Jackfruit | Vegan Beer Brat |
Top 3 iconic restaurants that summarize the city |
|
|
Fitness/Health Conscientiousness | 💪💪💪💪💪💪💪💪💪💪 | 💪💪💪💪💪💪💪💪💪💪 |
Abundance of Food Trucks | 🚚🚚🚚🚚🚚🚚🚚🚚🚚🚚 | 🚚🚚🚚🚚🚚🚚🚚🚚🚚🚚 |
Foodie Scene | 🍴🍴🍴🍴🍴🍴🍴🍴🍴🍴 | 🍴🍴🍴🍴🍴🍴🍴🍴🍴🍴 |
Vegan Friendly | 🌱🌱🌱🌱🌱🌱🌱🌱🌱🌱 | 🌱🌱🌱🌱🌱🌱🌱🌱🌱🌱 |
In Chesapeake, you'll find that the Chesapeake Blue Crab is more than just a dish; it's a celebration of the city's strong ties to the waters of the Chesapeake Bay. Places like Wicker's Crab Pot Seafood offer an authentic taste of this local delicacy. Meanwhile, moving to Milwaukee introduces you to a city proud of its German heritage, reflected in its love for Beer Brats and Polish Sausage. Unique eateries such as Mader’s provide an insight into the city’s culinary heritage. The Milwaukee public market in the Historic Third Ward district, famous for its artisanal foods, is a must-visit for new residents looking to immerse themselves in Milwaukee's diverse food scene.
Chesapeake vs. Milwaukee Restaurant Comparison
Food plays a crucial role in making a new city feel like home. This restaurant comparison between Chesapeake and Milwaukee aims to help you discover your next favorite eatery, easing the transition and enriching your culinary adventures in your new city.
Chesapeake | Milwaukee | What You'll Love |
---|---|---|
The Butcher's Son | Bavette La Boucherie | Offers high-quality meats and gourmet dining experience similar to The Butcher's Son. |
Passion The Restaurant | Sanford Restaurant | Creative and upscale dining, matching the culinary artistry found at Passion. |
Off The Hook Seafood & Chophouse | Harbor House | Fresh, waterfront seafood dining offering a parallel to Off The Hook's experience. |
Amber Lantern | Odd Duck | Known for its unique and eclectic dishes, akin to the diverse menu Amber Lantern provides. |
Big Ugly Brewing | Lakefront Brewery | Both offer a laid-back atmosphere with high-quality craft beers. |
Wicker's Crab Pot Seafood | St. Paul Fish Company | Specializes in fresh seafood, serving a comparable taste to Wicker's offerings. |
Bergey's Breadbasket Bakery & More | Peter Sciortino's Bakery | Both are iconic spots for freshly baked goods and sweet treats. |
Yama Sushi Bar | Screaming Tuna | A sushi and Asian bistro with a vibe and menu that resonate with Yama Sushi Bar enthusiasts. |
Broken Egg Bistro | Blue's Egg | Serves a hearty, gourmet breakfast with a similar charm to Broken Egg Bistro. |
Julie's Cafe | Café Hollander | Comfortable, casual dining with a menu that echoes the homey feel of Julie's Cafe. |
When moving from Chesapeake to Milwaukee, the anticipation of exploring new dining experiences can be thrilling. For seafood lovers, the transition from dining at Off The Hook Seafood & Chophouse to enjoying the lakeside ambiance at Harbor House offers a seamless culinary journey, with both establishments priding themselves on fresh, high-quality ingredients. Meanwhile, craft beer enthusiasts who savored the local brews at Big Ugly Brewing will find comfort and camaraderie at Lakefront Brewery, a staple in Milwaukee's thriving beer scene renowned for its wide selection of handcrafted beers. This move doesn't mean leaving culinary favorites behind; instead, it's an opportunity to expand your palate and discover Milwaukee's vibrant food scene, reminding you of the flavors of home while introducing you to new delights.

Ready to start your move?
Chesapeake vs. Milwaukee Real Estate & Living Facts
Real estate is a crucial aspect of relocating, and understanding how housing compares between Chesapeake, VA, and Milwaukee, WI, can ease the transition. This guide highlights cost, architecture, and lifestyle differences to aid in your decision.
Comparison | Chesapeake | Milwaukee |
---|---|---|
Typical Architecture Style | Colonial, Ranch | Craftsman, Bungalow |
Walkability | 👟👟👟👟👟👟👟👟👟👟 | 👟👟👟👟👟👟👟👟👟👟 |
Bikeability | 🚲🚲🚲🚲🚲🚲🚲🚲🚲🚲 | 🚲🚲🚲🚲🚲🚲🚲🚲🚲🚲 |
Urban Lifestyle | 🏛️🏛️🏛️🏛️🏛️🏛️🏛️🏛️🏛️🏛️ | 🏛️🏛️🏛️🏛️🏛️🏛️🏛️🏛️🏛️🏛️ |
Most popular items mentioned in real estate listing | Spacious backyards, quiet streets | Proximity to coffee shops and parks |
When comparing Chesapeake, VA, to Milwaukee, WI, you'll find distinct differences in the housing landscape that could influence your decision. Milwaukee's lower median home price and rent offer a more accessible entry point to homeownership or renting. The city's emphasis on walkability and bikeability highlights a robust urban lifestyle, making amenities easily accessible without a car. This contrasts with Chesapeake’s more suburban feel, where homes often boast larger backyards and a quieter neighborhood vibe. Moreover, Milwaukee's rich architectural diversity, featuring Craftsman and Bungalow styles, adds unique character to the city's neighborhoods. This detailed comparison aims to give you a clearer picture of what to expect from each city beyond just numbers.

Pet-friendly Neighborhoods in Milwaukee, WI
1. Bay View: Known for its community feel, you'll find an abundance of pet-friendly cafes and a popular dog park, ensuring your furry friend will always feel welcome.
2. Third Ward: This neighborhood boasts stylish pet-friendly apartments and several boutiques like Third Ward Dog, where you can pamper your pooch with the latest trends.
3. Wauwatosa: Offering numerous parks and green spaces, such as the spacious Hart Park, it's a paradise for pets who love the outdoors, making walks and playdates a part of your daily routine.
Chesapeake vs. Milwaukee Weather Considerations
When planning a move from Chesapeake, VA, to Milwaukee, WI, understanding the weather differences is crucial. This comparison will highlight the climate changes you can expect. Specifically, we'll explore the weather variations between Chesapeake and Milwaukee to help you prepare for your new home environment.
Chesapeake, VA
Milwaukee, WI
Average Summer High/Low (°F)
Average Summer High/Low (°F)
Chesapeake, VA
Milwaukee, WI
Average Winter High/Low (°F)
Average Winter High/Low (°F)
Chesapeake, VA
Milwaukee, WI
Annual Rainfall (Inches)
Annual Rainfall (Inches)
Chesapeake, VA
Milwaukee, WI
Annual Snowfall (Inches)
Annual Snowfall (Inches)
Comparison | Chesapeake | Milwaukee |
---|---|---|
Air Quality | Good | Moderate |
Natural Disasters | Hurricanes, floods | Snowstorms, cold waves |
Days of Sunshine per Year | ☀️☀️☀️☀️☀️ | ☀️☀️☀️☀️☀️ |
Avg. UV Index | 🕶️🕶️🕶️🕶️🕶️🕶️🕶️🕶️🕶️🕶️🕶️ | 🕶️🕶️🕶️🕶️🕶️🕶️🕶️🕶️🕶️🕶️🕶️ |
Avg. Annual Humidity | 💦💦💦💦💦💦💦💦💦💦 | 💦💦💦💦💦💦💦💦💦💦 |
Transitioning from Chesapeake's humid subtropical climate to Milwaukee's humid continental climate means preparing for cooler summers and significantly colder winters. Milwaukee experiences a notable drop in the average winter temperature, dipping as low as 18°F, compared to Chesapeake's milder 32°F lows. Additionally, you'll encounter more snowfall in Milwaukee, significantly higher than Chesapeake's average, which presents a unique set of challenges and opportunities for winter activities. Despite the changes, both cities share similar concerns over air quality and top seasonal allergies, indicating some continuity in what you might have already been accustomed to.
Ready to start your move?
Money, Economy, and Job Market Considerations for Moving from Chesapeake to Milwaukee
When considering a move from one city to another, it's crucial to weigh the financial implications. Understanding the differences in cost of living between Chesapeake, VA, and Milwaukee, WI , is essential for preparing your budget and financial planning. This comparison aims to provide you with a clearer picture of what to expect in terms of money and finance.
Comparison | Chesapeake | Milwaukee |
---|---|---|
Avg. Household Income | $88,815 | $46,637 |
Cost of Living Index | 96.6 | 101.9 |
State Income Tax | 5.75 | 7.65 |
Avg. Property Tax | 0.79 | 2.17 |
Avg. Sales Tax | 6 | 5.6 |
Top 3 Industries | Defense, Transportation, Retail | Manufacturing, Healthcare, Educational Services |
Affluence | Moderate | Lower |
Poverty | Lower | Higher |
Homelessness | Minimal | Moderate |
In comparing the financial landscape of Chesapeake, VA, and Milwaukee, WI, several significant differences emerge. Chesapeake boasts a higher average household income and a lower poverty rate, painting a picture of relative affluence compared to Milwaukee. However, this advantage comes at the cost of a higher living index and property taxes. Milwaukee, while having lower average income levels and a higher poverty rate, offers a more affordable cost of living and slightly lower sales tax rates. This discrepancy underscores the importance of considering salary adjustments and the potential impact on your lifestyle and savings when planning a move. Understanding the prominent industries can also help in navigating job markets and career opportunities in both locales.
Chesapeake vs. Milwaukee Political & Religious Comparison
When planning your move from Chesapeake, VA to Milwaukee, WI, understanding the communities you will encounter is crucial. This comparison offers a quick, at-a-glance snapshot of the political and religious makeup of the residents, providing insights into your new neighbors. This is a comparison of the politics and religion between Chesapeake & Milwaukee, aimed at helping you settle in smoothly.
Chesapeake | Milwaukee | |
---|---|---|
Political Make-up | Conservative | Liberal |
Local Politics | City of Chesapeake's Government | City of Milwaukee's Government |
Religion | Christian Dominance | Diverse, with a strong Catholic presence |
In Chesapeake, the local culture and politics tend to lean more conservative, with Christianity playing a significant role in community activities and social gatherings. This contrast sharply with Milwaukee, where the political climate is notably more liberal, reflecting its diverse population. Milwaukee's religious landscape is varied, with a prominent Catholic community alongside other faiths. This diversity in both politics and religion underlines the cultural shift you'll experience when moving from Chesapeake to Milwaukee, offering a broad spectrum of perspectives and community engagements.
Chesapeake vs. Milwaukee Traffic and Public Transit Considerations
Moving from one city to another can bring about exciting changes, especially when it comes to your daily commute. This comparison aims to provide a clearer picture of what driving and transiting is like between Chesapeake, VA, and Milwaukee, WI. Understanding how these aspects differ will help you adjust to your new home more easily.
Comparison | Chesapeake | Milwaukee |
---|---|---|
Avg Commute Time (in minutes) | 25 | 22 |
Traffic Congestion | 🚦🚦🚦🚦🚦🚦🚦🚦🚦🚦 | 🚦🚦🚦🚦🚦🚦🚦🚦🚦🚦 |
Availability of Public Transit | 🚇🚇🚇🚇🚇🚇🚇🚇🚇🚇 | 🚇🚇🚇🚇🚇🚇🚇🚇🚇🚇 |
Can you get by without car? | No | Yes |
When comparing the daily commute in Chesapeake and Milwaukee, a noticeable difference is the average commute time, with Milwaukee offering a slightly shorter commute. However, Milwaukee has higher traffic congestion, which may affect driving times but also indicates a denser urban area with possibly more accessible amenities. Public transit in Milwaukee is markedly more available and efficient, making it a viable option for daily commuting. This contrasts with Chesapeake, where a personal vehicle is almost essential due to limited public transit options. This information highlights the importance of considering your commute and transportation preferences when moving to a new city.



Additional Resources
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Popular Chesapeake to Wisconsin Routes
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