Whether you're saving up for a vacation, tackling student loans, or just trying to keep up with rising expenses, a side gig can be a game-changer. And if you're living in the Windy City, you're in luck—Chicago offers a wide variety of side hustle opportunities across industries, skill sets, and income levels.
In this guide, we’ll explore the top side gigs in Chicago, from gig economy apps to local freelance work and part-time gigs with growth potential. Whether you want to work nights, weekends, or in-between your 9-to-5, there’s something here for you.
Chicago is one of the largest metropolitan areas in the U.S., with a population of nearly 9 million in the greater area. That scale brings demand—demand for services, deliveries, dog walkers, and creative freelancers.
The city’s diverse economy also helps. With thriving industries like healthcare, logistics, food, and finance, there are plenty of niches to tap into for flexible, part-time, and freelance work.
Chicagoans are also among the most entrepreneurial in the U.S., according to data from the U.S. Census Bureau. That DIY mindset makes it a hotbed for successful side hustles.
Gig economy apps are a tried-and-true option, and Chicago is a major market for rideshare and delivery services.
With busy neighborhoods like River North, Wicker Park, and downtown’s Loop, rideshare demand in Chicago is consistent—especially on nights and weekends. Drivers can sign up with Uber or Lyft to earn flexible income with peak-hour bonuses and tips.
Estimated earnings: $18–$28/hour (after expenses)
Prefer not to drive people around? Chicago’s food scene is always bustling, and delivery services like DoorDash, Uber Eats, and Instacart are perfect for earning on your own schedule.
Hot tip: Deliver in high-density areas like Lincoln Park, Lakeview, or West Loop for more orders and shorter travel distances.
TaskRabbit connects Chicagoans with people who need help assembling furniture, moving, or doing odd jobs. If you're handy or just like helping out, you can set your own rates and availability.
Set up a profile on TaskRabbit Chicago and get started with gigs that pay hourly or per task.
Common tasks: Mounting TVs, IKEA assembly, yard work
Typical earnings: $20–$60/hour, depending on the task
If you're skilled in writing, graphic design, programming, or social media, remote freelancing is a high-potential side gig. Set your own pricing and take on short- or long-term contracts via platforms like:
Chicago has a vibrant creative and tech scene, so you can also market yourself locally through LinkedIn or Chicago-area Facebook groups.
Pro tip: Consider joining coworking hubs like 1871 or WeWork to connect with local entrepreneurs who may need your skills.
From furniture flips to handmade crafts, selling online locally is a profitable and relatively low-effort side gig in Chicago. Apps like OfferUp, Craigslist, and Facebook Marketplace are free to use and widely popular in the city.
Common resale categories include:
Extra tip: Look into sourcing free items via Freecycle or local “Buy Nothing” groups.
Chicago is a very dog-friendly city, and services like Rover or Wag let you sign up as a pet sitter, walker, or even an overnight host.
You can build up a client base and set your own rates and schedule. Popular neighborhoods for pet gigs include Logan Square, Lincoln Park, and Hyde Park.
Earnings: $15–$35 per walk or visit
If you have an extra room or a separate unit, short-term rentals on Airbnb can bring in serious cash—especially during the summer festival season. Chicago laws require registration, so make sure you're in compliance with city guidelines.
Don’t have a space to rent? You can still earn by renting out storage space via platforms like Neighbor, where people pay to store seasonal gear, furniture, or moving boxes in garages or basements.
If you’re strong in math, languages, or test prep, tutoring is an in-demand side gig—especially in a city with hundreds of thousands of students.
Platforms like Wyzant, Varsity Tutors, or Skillshare allow you to teach in-person or virtually.
Tip: Consider offering ACT/SAT tutoring or help with college applications—services often in demand across Chicago’s competitive high schools.
Chicago’s summer is packed with events like Lollapalooza, Taste of Chicago, and the Air and Water Show. Seasonal work with event vendors, ticketing companies, or crowd management firms like Allied Universal or Staff Pro can bring in great weekend cash.
Also look out for opportunities at:
If you have a truck or large SUV and like working independently, Sharetown is a unique way to earn money by picking up and reselling returned mattresses and furniture. Reps work flexible hours and get paid for each sale they complete—many earn several hundred to a few thousand dollars per month.
The Chicago metro area is consistently active for pickups, and it’s a great gig for self-starters. Learn more or apply at Sharetown.com.
Want full control of your side hustle? Start something local:
Check out resources like Chicago Small Business Center or Score Chicago to get started.
The best side gig in Chicago depends on your availability, skills, and financial goals. Whether you want to work from home, hit the streets, or meet people face-to-face, the city’s economy offers plenty of flexible and profitable opportunities.
Start with one that fits your lifestyle—and don’t be afraid to experiment until you find your niche. With the right side hustle, you could unlock a new stream of income and new possibilities.
