Top side hustles in Milwaukee
Milwaukee lives two lives. From June through September the lakefront hosts one festival after another and the city fills with visitors. From November through March it is a snow town that runs on salt, shovels and delivery apps. If you learn both seasons, the best side hustles in Milwaukee can bring in steady money all year at a cost of living well below Chicago, an hour and a half down I-94.
This guide covers 18 side gigs in Milwaukee with typical pay, startup costs and local tips, plus the Wisconsin tax rules that apply to side income. Spoiler: there is no city income tax to worry about.
Why Milwaukee is a two-season side hustle city
Summer is festival season. Summerfest takes over Henry Maier Festival Park on the lakefront for several weekends from late June into July, followed by PrideFest, Festa Italiana, German Fest, Irish Fest, Mexican Fiesta and more. The Wisconsin State Fair in West Allis runs in early August, and Brewers games at American Family Field draw tailgaters all season.
Winter is service season. Lake Michigan weather brings regular snowfall, icy sidewalks and salty roads. Homeowners, landlords and small businesses need snow cleared, cars cleaned and groceries delivered when nobody wants to go out.
The economy in between is solid: Northwestern Mutual downtown, Fiserv, Rockwell Automation, Harley-Davidson, ManpowerGroup, Froedtert and Advocate Health hospitals, plus Marquette University, UW-Milwaukee and MSOE. Bucks games at Fiserv Forum and Marquette basketball keep the Deer District busy in winter.
Top picks: the best side hustles in Milwaukee
1. Festival and game-day rideshare
Summerfest nights, Brewers games, Bucks games at Fiserv Forum and Friday nights in the Third Ward, Walker's Point and on Brady Street are the best windows. Early-morning runs to Milwaukee Mitchell International round out the week. See our Lyft and Uber guide for sign-up steps.
2. Food and grocery delivery
DoorDash, Uber Eats and Instacart are busy on the East Side, in Bay View and downtown, while Wauwatosa, Brookfield and the North Shore suburbs bring larger grocery orders. Snowy evenings are when tips climb.
3. Snow removal
Milwaukee requires property owners to keep sidewalks clear, and plenty of seniors and duplex landlords would rather pay. Sell seasonal contracts in Bay View, Wauwatosa, Shorewood and West Allis before the first storm. A snow blower lets you take on more clients.
4. Festival and event staffing
Summerfest, the ethnic festivals, the State Fair and stadium concessions hire huge numbers of temporary workers. Many nonprofit groups staff beer and food stands and share proceeds with volunteers.
5. Duplex and rental turnover cleaning
Milwaukee is famous for its duplexes and older flats, and landlords need units cleaned between tenants, especially around student turnover near Marquette and UWM. Short-term rentals near the lakefront fill up during festivals.
6. Handyman and landlord support
Small landlords with a few duplexes need someone dependable for repairs, painting, lock changes and turnover punch lists. Riverwest, Washington Heights and Bay View homes are full of century-old quirks. Leave licensed electrical and plumbing work to the pros.
7. Pet sitting and dog walking
Apartment dwellers in the Third Ward, East Side and Walker's Point and families in Wauwatosa and Whitefish Bay need walks and overnight care. Summer travel and the holidays book out early.
8. Lawn care and yard cleanup
The same clients who pay you to shovel in January want mowing from May through October and leaf cleanup in November. Brookfield, Mequon and Oak Creek have plenty of suburban lots.
Where side gigs in Milwaukee pay best
Milwaukee is compact enough that you can build a tight route, as long as you pick the right part of town for your hustle:
- Third Ward, downtown and the Deer District: hotels, offices, Fiserv Forum and the festival grounds make this the hub for rideshare, delivery and event staffing.
- East Side, Brady Street and Riverwest: students, young professionals and lots of apartments. Strong for dog walking, bike delivery, moving help and tutoring.
- Bay View and Walker's Point: restaurants and bars, older homes and plenty of pet owners. Good for delivery, handyman work and pet care.
- Wauwatosa, Shorewood and Whitefish Bay: higher incomes and established homes that need snow removal, lawn care, cleaning and holiday lights.
- Brookfield, Mequon and Oak Creek: bigger suburban lots and busy families for yard work, detailing and in-home tutoring.
Choose one area and get known there first. In a city where winter turns a 10-minute drive into 25, a dense client list is worth more than a slightly higher rate across town.
Side jobs in Milwaukee compared
| Side hustle | Typical pay | Startup cost | Time to first dollar |
|---|---|---|---|
| Rideshare | $16–$24/hr gross | Eligible car | 1–2 weeks |
| Delivery | $15–$22/hr gross | Car or bike | Under 1 week |
| Snow removal | $30–$70/job | $30–$800 | First snowfall |
| Festival staffing | $15–$22/hr | $0 | Next festival |
| Rental cleaning | $25–$40/hr | $75–$150 | 1–2 weeks |
| Handyman | $40–$65/hr | $100–$400 | 1–2 weeks |
| Pet sitting | $18–$28/walk | $0 | 1–3 weeks |
| Lawn care | $35–$60/mow | $100–$400 | Days |
Want to see how many hours of a given gig it takes to hit your monthly goal? Plug in your numbers:
Side Hustle Income Calculator
Plug in your rate and hours to see monthly and yearly take-home — and how long until you hit a goal.
More summer side gigs on the lakefront
9. Game-day and festival parking
Homes and businesses near American Family Field, the State Fair Park in West Allis and the lakefront can rent driveway and lot space on busy days. Check neighborhood parking rules first.
10. Boat cleaning and marina help
Boat owners at lakefront marinas pay for washing, detailing and spring and fall prep. It is short and seasonal but pays well per job.
11. Moving help
Student turnover around Marquette and UWM in late spring and late summer, plus duplex stairs, make moving help a reliable earner. A folding hand truck saves your back.
12. Farmers markets and pop-ups
Neighborhood farmers markets, the Milwaukee Public Market area and holiday craft fairs are great testing grounds for baked goods (within Wisconsin rules), candles, prints and Milwaukee-themed apparel.
Winter side gigs that beat the cold
13. Interior car detailing
Salt and slush destroy carpets and floor mats from November to March. Interior-focused winter packages sell better than exterior washes, and spring brings a rush of full details.
14. Holiday light installation
North Shore and suburban homeowners pay to have lights hung in November and taken down in January. Pair it with gutter cleaning.
Online and skill-based side gigs
Remote work pays national rates while Milwaukee rent stays modest, which makes these especially worthwhile in the long winter.
15. Freelance writing, design and marketing
Financial services, manufacturing and healthcare companies across southeast Wisconsin hire contract help. Build reviews on Fiverr, then pitch local businesses. Our digital marketing side hustle guide shows how to package services.
16. Tutoring
Families in Whitefish Bay, Mequon, Brookfield and Elm Grove pay for math, science and ACT prep. Marquette and UWM students can tutor in person; anyone can tutor online.
17. Bookkeeping and virtual assistance
Small landlords, contractors and restaurants need help with invoices, rent tracking and scheduling. Tax season is your busiest stretch.
18. Reselling
Estate sales in Wauwatosa and the North Shore, thrift stores and garage sales feed eBay and Facebook Marketplace. Vintage Brewers, Bucks and Packers gear sells to fans everywhere.
Wisconsin tax rules for Milwaukee side hustlers
- State income tax: Wisconsin uses graduated brackets with rates from 3.5% to 7.65%. Most side hustlers with a regular job land in the middle brackets on their extra income.
- No local income tax: Milwaukee and other Wisconsin cities do not levy income taxes, unlike Ohio cities or Detroit.
- Self-employment tax: 15.3% federal on net profit, plus federal income tax. Estimate yours with the self-employment tax calculator.
- Sales tax: if you sell taxable goods, get a Wisconsin seller's permit. Inside the City of Milwaukee the combined rate is 7.9% (5% state, 0.9% county and 2% city); parts of Milwaukee County outside the city are lower.
- Licenses: there is no general state business license. The City of Milwaukee License Division handles specific licenses, and short-term rentals and food sales have their own rules.
How to start making money in Milwaukee this month
- Pick one hustle for this season. Festival work and lawn care in summer, snow removal and delivery in winter.
- Plan your off-season pair. Offer clients a year-round package so they stay with you when the weather turns.
- Get listed. Gig apps for driving and delivery; Nextdoor and neighborhood Facebook groups for services.
- Book the calendar. Summerfest, the ethnic festivals, the State Fair, Brewers and Bucks schedules and the first snow.
- Set aside 25–30% of profit. That covers state, federal and self-employment tax for most people.
- Review after 30 days. Keep the gig with the best hourly profit and drop the rest.
Nearby city guides
Compare Milwaukee with the best side hustles in Chicago, Minneapolis and Detroit. Milwaukee's festival summers and duplex-heavy housing give it a character all its own, and Better Side Hustles readers here who plan for both seasons earn the most consistently. Pick one idea, commit for 90 days and track every dollar.
Frequently asked questions
What are the best side hustles in Milwaukee?
Festival-season rideshare and event staffing, food delivery, snow removal, lawn care, duplex and rental cleaning, handyman work in older homes, pet sitting on the East Side and in Bay View, and remote freelancing are the strongest options. Milwaukee's summer festivals and long winters reward people who line up one hot-weather gig and one cold-weather gig.
How can I make money in Milwaukee fast?
Delivery apps such as DoorDash, Uber Eats and Instacart can pay within a week of approval. Staffing agencies and concession operators hire heavily for Summerfest, the ethnic festivals and Brewers and Bucks games. Rover and TaskRabbit can book in days, and after a snowfall, shoveling neighbors' walks can pay the same day.
Does Milwaukee have a city income tax?
No. Wisconsin does not allow city income taxes, so side hustlers in Milwaukee pay only Wisconsin state income tax, which uses graduated rates from 3.5% to 7.65%, plus federal income and self-employment tax. If you sell taxable goods in the city, the combined sales tax rate is 7.9% after Milwaukee added its own city sales tax.
Do I need a business license for a side hustle in Milwaukee?
Wisconsin has no general statewide business license, and many simple service side hustles do not need one. You will need a Wisconsin seller's permit to sell taxable goods, and food sales, short-term rentals and some trades require specific licenses or permits. Check with the City of Milwaukee License Division before you scale.
How much do side gigs in Milwaukee pay?
Delivery and rideshare typically gross $15 to $24 an hour before gas. Skilled services such as handyman work, pressure washing and freelancing often pay $35 to $70 an hour once you have repeat clients. Working 8 to 15 hours a week, most people earn roughly $400 to $1,400 a month, with summer and storm weeks paying more.
What are good winter side hustles in Milwaukee?
Snow removal is the obvious winner, especially seasonal contracts for seniors, landlords and small businesses. Winter also brings higher delivery tips, interior car detailing to clean out salt, holiday light installation, indoor event staffing for Bucks and Admirals games, and remote work like tutoring and freelancing that you can do from a warm apartment.
Better Side Hustles Editorial Team. We research side hustles the practical way — platform fees, real pay ranges and what it takes to land your first dollar. How we write our guides.
Last reviewed October 26, 2026. Pay ranges are estimates and vary by city, season and effort. This article may contain affiliate links; see our disclosure.
