Looking to Retire? Find Out Why This Wisconsin City is Perfect for Affordable Weekend Escapes

For retirees looking to travel more during their golden years, finding the right home base makes all the difference. Milwaukee, Wisconsin—often overshadowed by its flashier Midwestern neighbor, Chicago—is a retirement destination worth considering for frequent travelers. This charming city on Lake Michigan offers excellent travel connectivity, a reasonable cost of living, and dozens of amenities that make it a perfect home base for adventurous retirees. 

Travel Accessibility

At the heart of Milwaukee’s travel offerings is Milwaukee Mitchell International Airport (MKE), a mid-sized airport that is as well-connected as it is convenient. 

Airport Capabilities 

With an airport score of 99, MKE serves more than 30 nonstop destinations across the United States, Mexico, and Canada. The airport is home to nine major airlines, including American, Delta, Southwest, United, Frontier, Spirit, and Sun Country, giving you competitive pricing options and plenty of routes.

Local Transit Options 

One major perk of choosing Milwaukee as your retirement destination is that this compact city is incredibly walkable. A stroll along the Milwaukee RiverWalk will take you on a three-mile path through downtown to the neighborhoods of Beerline B, Old World Third Street Entertainment District, ending in the Historic Third Ward.

If you prefer to take public transit, the city of Milwaukee offers multiple bus lines, including the new Connect 1 Bus Rapid Transit Line (BRT) that will take you through the entire county. Take the two-mile streetcar, called The Hop, which cruises through Milwaukee’s most popular neighborhoods entirely for free! 

Biking has also become an easy and accessible option in recent years with the introduction of Milwaukee’s bike share program, Bublr Bikes, which has stations located throughout downtown and Wauwatosa.

Multiple Transit Options 

Beyond air travel, Milwaukee offers several other transportation options:

• Amtrak service: The Hiawatha train connects Milwaukee to Chicago with seven daily round trips, making O’Hare easily accessible for international flights. The Empire Builder line takes you west through the Dakotas and Montana, all the way to Seattle.
• Lake Michigan ferry: From May to October, the Lake Express High-Speed Ferry connects Milwaukee to Muskegon, Michigan, offering a unique way to explore Michigan while bypassing Chicago traffic.
• Highway access: Milwaukee sits at the intersection of three major interstates (I-94, I-43, and I-41), providing excellent road trip options throughout the Midwest.
• Cruise port: The Port of Milwaukee welcomes Great Lakes cruise ships during the summer months, offering another fun and unique travel option.

Cost of Living and Affordability

One compelling reason to choose Milwaukee for retirement is its affordability, which means even more funds to support your traveling. 

Housing 

Milwaukee County offers remarkably affordable housing compared to the national average. The median monthly housing cost in Milwaukee is $1,156, compared to the national average of $2,120. This affordability means retirees can potentially downsize from higher-cost areas and pocket the difference for travel funds. 

Transportation and Food 

Daily living expenses, like transportation and food, remain reasonable. Residents pay approximately $653 monthly for food and $1,083 for transportation. For those using public transit, Milwaukee’s system (MCTS) offers reduced fares for seniors.

Health Care 

According to the U.S. News and World Report, Wisconsin ranks No. 26 among the top 100 cities for health care. Fidelity estimates that a 65-year-old who retired in 2024 will need approximately $165,000 to cover post-tax health care costs—with the average 65-year-old couple spending around $12,800 in their first year of retirement. So, you’ll be happy to take advantage of Milwaukee’s excellent health care systems. 

Lifestyle Considerations for Retirees

Between travels, Milwaukee offers an impressive amount of activities and amenities to enhance your retirement. 

Cultural Attractions 

With over 300 arts and entertainment establishments in Milwaukee County alone, you’ll never lack for cultural experiences. The city is home to 28 museums, including the Milwaukee Art Museum with its famous Burke Brise Soleil wings. The Milwaukee Symphony Orchestra, Ballet, and several theater companies offer you world-class entertainment. 

Known as the “City of Festivals,” Milwaukee hosts over 100 festivals a year, ranging from the Food Truck Fest to the Weird Fest, meaning you will never have to spend a weekend bored at home.

Outdoor Recreation 

Milwaukee appeals to both city dwellers and outdoor enthusiasts. With direct access to Lake Michigan, the city boasts 1,400 acres of beach and lakefront parks, 15,000 acres of parkland, and more than 135 miles of trails throughout the county. In the winter, you can enjoy cross-country skiing, ice skating, and snowshoeing. 

Other Things To Consider

There are a few important lifestyle factors worth considering before deciding to make Milwaukee your permanent residence during retirement.

Climate

Milwaukee experiences all four seasons, which brings both advantages and challenges. Winters can be extreme with over 48 inches of snow annually, while summers average a pleasant 80°F. The fall and spring offer mild and beautiful conditions. 

Community

About 15% of Milwaukee residents are over the age of 65, with several adult and retirement communities throughout the metro area. The city features strong neighborhood associations and community centers that foster social connections.

Health Care Quality

Milwaukee offers excellent health care with Froedtert Hospital ranked No. 1 in the Milwaukee metro and No. 2 across Wisconsin by the U.S. News & World Report. The county has 35 hospitals and over 1,400 health care establishments. While the health care access score is 35/100, residents have quick access to Chicago’s medical systems.  

Tax Considerations

Wisconsin exempts Social Security tax benefits and offers property tax relief programs through a homestead credit for seniors. Income taxes range from 3.50% to 7.65%, higher than some other popular retirement destinations, but there’s no estate or inheritance tax at the state level. Residents pay approximately $615 a month in county taxes. 

The Bottom Line

Milwaukee offers travel-loving retirees an ideal combination of connectivity, affordability, and quality of life. The city’s excellent airport and highway network make frequent travel convenient, while its reasonable cost of living means even more funds for adventures. 

Between trips, you’ll enjoy vibrant cultural experiences and beautiful outdoor spaces along Lake Michigan, all without the congestion and high costs of other metropolitan areas.

Before making the move, consider visiting Milwaukee during different seasons to experience its climate extremes. Remember that retirement relocation goes beyond the numbers; Milwaukee’s  Midwestern friendliness, sense of community, and travel accessibility make it an excellent retirement destination.