Top side hustles in Chicago
Chicago pays people who know how to work its rhythms. The city packs nearly three million people into dense neighborhoods, pulls in conventions and tourists by the planeload, and throws a brutal winter at everyone who stays. Each of those facts creates paid work. This guide breaks down the best side hustles in Chicago right now: what each one typically pays, what it costs to start, and the local timing that separates a $300 month from a $1,500 one.
Whether you want quick cash between shifts or a second income stream you can build for years, the side gigs in Chicago below are ranked roughly by how fast and reliably they pay.
Why Chicago is built for side income
Most cities give you either density or money. Chicago gives you both. A few things to keep in mind as you choose:
- Neighborhood density. Lakeview, Lincoln Park, Logan Square, Wicker Park and the West Loop pack thousands of renters into a few square miles. That means short delivery trips, walkable dog-walking routes and lots of potential clients within one zip code.
- Two airports and a convention machine. O'Hare and Midway feed rideshare all day, and McCormick Place hosts giant trade shows like the Chicago Auto Show in February and the restaurant industry show in May. Conventions mean hotel demand, event staffing and late-night rides.
- A stacked sports and festival calendar. Cubs games at Wrigley, Sox games on the South Side, Bears at Soldier Field, Bulls and Blackhawks at the United Center, Lollapalooza in Grant Park every summer and the Chicago Marathon each October.
- Winter. When the lake-effect snow and wind arrive, delivery tips climb, nobody wants to shovel, and the people who show up get paid.
The professional base helps too. Headquarters and big offices for companies like United Airlines, McDonald's, Abbott and Allstate, plus hospital systems like Northwestern Medicine, mean plenty of busy, well-paid households that outsource chores and small businesses that hire freelancers.
The best side hustles in Chicago: top picks
These eight pay the fastest or most consistently for the average Chicagoan. Start here.
1. Rideshare driving
The money in Chicago rideshare is in the windows: O'Hare runs at 5 a.m., the post-game crush around Wrigleyville, Friday and Saturday nights in River North and the West Loop, and convention weeks downtown. Rainy and snowy evenings push surge pricing up. Watch for parking costs and tolls. Our Lyft and Uber guide covers sign-up and vehicle requirements.
2. Food and grocery delivery by car or bike
DoorDash, Uber Eats, Grubhub and Instacart all run heavy in Chicago. Downtown, Streeterville and the Gold Coast reward bike and e-bike couriers because parking is a nightmare, while suburbs like Evanston, Oak Park and Naperville work better by car. Dinner rush on a cold night is the sweet spot.
3. Dog walking and pet sitting
High-rise living in Streeterville, the South Loop and Lakeview means lots of dogs and owners who work long days. Midday walks on Rover or Wag build a route quickly, and overnight sitting books out around Thanksgiving, Christmas and summer travel. A sturdy hands-free dog leash makes multi-dog walks easier.
4. Apartment and move-out cleaning
A huge share of Chicago leases turn over around May 1 and again in late summer, and landlords want units spotless between tenants. Recurring cleaning for busy condo owners and short-term rental turnovers fill the rest of the year. One property manager can keep you booked.
5. Snow shoveling
Chicago requires property owners to clear their sidewalks, and plenty of two-flat owners, seniors and landlords would rather pay someone. Sell a seasonal package in October to neighbors on your block in Portage Park, Jefferson Park or Beverly. A good shovel and a bag of ice melt is all you need to start.
6. Handyman and furniture assembly
Chicago's housing stock is old: brick two-flats, bungalows and greystones full of sticking windows, wobbly railings and dated fixtures. TaskRabbit stays busy with furniture assembly and TV mounting, especially during moving season. Avoid electrical and plumbing work that requires a licensed tradesperson.
7. Freelance marketing, writing and design
Chicago is a major agency and corporate town, and plenty of local firms need overflow help with copy, decks, social media and ads. Start on Fiverr to build reviews, then pitch Chicago small businesses directly. Our digital marketing side hustle guide shows how to package services.
8. Event staffing and concessions
Staffing agencies hire for Soldier Field, the United Center, Wrigley, McCormick Place and summer festivals. Shifts include ticket scanning, ushering, bartending, setup and teardown. Lollapalooza weekend alone can fill your calendar.
Driving or delivering? Plug in your real gas, parking and mileage numbers before you commit, because Chicago costs eat into gross pay fast:
Gig Driver Earnings Calculator
Uber, Lyft, DoorDash or Instacart — see what you really earn per hour after gas and wear on your car.
Side jobs in Chicago compared
| Side hustle | Typical pay | Startup cost | Time to first dollar |
|---|---|---|---|
| Rideshare | $20–$30/hr gross | Eligible car | 1–2 weeks |
| Food delivery | $16–$25/hr gross | Bike or car | Under 1 week |
| Dog walking / pet sitting | $20–$30/walk | $0 | 1–3 weeks |
| Apartment cleaning | $28–$45/hr | $75–$150 | 1–2 weeks |
| Snow shoveling | $30–$70/job | $30–$100 | First snowfall |
| Handyman / assembly | $40–$75/hr | $100–$400 | 1–2 weeks |
| Freelancing | $30–$80/hr | Laptop | 2–6 weeks |
| Event staffing | $17–$25/hr | $0 | Next big event |
| Parking spot rental | $20–$50 per event | $0 | Next home game |
Seasonal side gigs in Chicago
Chicago has two economies: summer and everything else. Smart hustlers plan for both.
9. Renting your parking spot
If you have a garage or pad near Wrigley Field, the United Center, Soldier Field or the South Side ballpark, list it on SpotHero or a neighborhood group for game days and concerts. Downtown residents with an unused deeded spot can rent it monthly.
10. Moving help
Walk-up apartments and narrow gangways make Chicago moves miserable, which is exactly why people pay. Dolly, TaskRabbit and Facebook groups post jobs constantly in late April and late August.
11. Balcony, rooftop and window-box gardening
Condo owners in Lincoln Park and the Gold Coast pay for spring planting and fall cleanup of balconies and roof decks. It is short, seasonal and often comes with referrals to the whole building.
12. Walking and food tour guide
Architecture, food and history tours run from spring through fall. Experienced guides list on Airbnb Experiences and GetYourGuide or work with existing tour companies in the Loop, Pilsen and Chinatown.
Skill-based side gigs for Chicago professionals
If you work in finance, healthcare, law or tech, your highest-paying side hustle is probably the skill you already use at work.
13. Tutoring and test prep
Selective enrollment high school testing, the SAT and college applications create steady demand from families on the North Side and in suburbs like Evanston, Wilmette and Naperville. Grad students at UChicago, Northwestern, Loyola, DePaul and UIC can tutor in person or online.
14. Bookkeeping and virtual assistance
Restaurants, contractors and real estate teams across Chicagoland need help with invoices, scheduling and QuickBooks cleanup. Tax season is the busiest stretch.
15. Real estate and headshot photography
Chicago's condo market moves year-round, so agents always need listing photos. Professionals in the Loop also book headshots for LinkedIn and company sites.
16. Online courses
Turn professional knowledge (Excel modeling, CPA exam tips, logistics software) into a course on Udemy or your own site. Slow to start, but it scales.
Selling and creative side hustles
17. Reselling and flipping
Alley finds on moving weekends are a Chicago tradition. Estate sales in Edgewater and Oak Park, thrift stores and curbside furniture feed Facebook Marketplace, eBay and Mercari. Vintage Bulls, Bears and Cubs gear sells to fans everywhere.
18. Handmade goods and pop-up markets
Neighborhood street fests run nearly every summer weekend, and holiday markets fill December. They are perfect for testing candles, prints and Chicago-themed apparel before selling online through Shopify or Etsy.
19. Music and fitness instruction
Chicago's music scene and fitness culture support private lessons and small-group training in parks along the lakefront each summer.
20. Short-term rental co-hosting
Rather than renting your own place, manage messaging, cleaning and restocking for an owner in exchange for a share of revenue. Make sure the unit is registered with the city first.
How to make money in Chicago starting this month
- Pick one hustle and one area. A single neighborhood keeps travel time low and referrals tight. Not sure which fits? Try the side hustle quiz.
- Set a monthly target. Work backward from the money you need to the hours you can commit.
- Get listed where Chicagoans look. Gig apps for driving and delivery, Nextdoor and neighborhood Facebook groups for local services, and a free Google Business Profile once you have a few clients.
- Mark the surge calendar. Home games, Lollapalooza, the Marathon, big McCormick Place shows and the first big snowfall.
- Collect reviews early. Five strong reviews beat any ad budget.
- Separate your money. Open a dedicated account and log every mile and receipt from day one.
Illinois taxes and Chicago rules for side hustlers
- State income tax: Illinois has a flat 4.95% individual income tax on your net profit.
- No city income tax: Chicago does not tax personal income, so you avoid the municipal income taxes found in Ohio and Detroit.
- Self-employment tax: 15.3% federal on net profit, on top of federal income tax. Estimate your set-aside with the self-employment tax calculator.
- Sales tax: if you sell physical products, register with the Illinois Department of Revenue. The combined rate inside Chicago is 10.25% or higher, among the steepest in the country.
- Licenses: Chicago's Department of Business Affairs and Consumer Protection handles business licenses. Short-term rental units must be registered with the city before they are advertised, and food and home-repair businesses have their own rules.
Nearby city guides
Compare Chicago with our guides to the best side hustles in Milwaukee, Indianapolis and Detroit. Chicago pays more per hour than any of them, but costs more too, which is why Better Side Hustles recommends Chicagoans track net profit, not gross. Pick one idea, give it 90 days, and let the numbers tell you what to keep.
Frequently asked questions
What are the best side hustles in Chicago?
The most dependable options are rideshare and delivery timed to games, concerts and bad weather, pet care in dense North Side neighborhoods, apartment cleaning and move-out help, snow shoveling, handyman work in older two-flats and bungalows, and remote freelancing for the many corporate and agency teams in the Loop. Pick one that fits the hours you can protect every week.
How can I make money in Chicago fast?
Delivery apps like DoorDash, Uber Eats and Instacart can pay within a week once you are approved. Rover dog walking, TaskRabbit furniture assembly and event staffing agencies that hire for stadiums and McCormick Place are also quick. If you live near Wrigley Field or Soldier Field, renting your parking spot on game days can pay the same weekend.
Do I need a business license for a side hustle in Chicago?
Many home-based service and online hustles can operate without one, but Chicago does require business licenses for a range of activities, and food sales, home repair and short-term rentals have their own rules. Short-term rental units must be registered with the city before you list them. Check with the Department of Business Affairs and Consumer Protection before you scale.
How much do side gigs in Chicago pay?
App-based work typically grosses $18 to $30 an hour before gas, tolls and parking, and nets less. Skilled local services such as handyman work, cleaning and photography often run $35 to $80 an hour once you have repeat clients. Most people working 8 to 15 hours a week earn somewhere around $500 to $1,800 a month.
How are side hustles taxed in Illinois?
Illinois charges a flat 4.95% state income tax on net profit, and Chicago has no separate city income tax. You also owe federal income tax and 15.3% self-employment tax. If you sell physical goods you will need to register for sales tax, which runs 10.25% or more inside Chicago. Setting aside 25 to 30% of profit is a safe rule.
Do I need a car for side hustles in Chicago?
No. Chicago is one of the best US cities for car-free hustling. Bike and e-bike delivery works well downtown and on the North Side, dog walking and pet sitting are hyperlocal, and the L and Metra make it easy to reach cleaning, tutoring or event shifts. A car mainly helps with rideshare, airport runs, Amazon Flex and suburban jobs.
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.
