Chicago is a bustling metropolis filled with opportunities for those looking to earn extra income through a side hustle. Whether you're a full-time professional, a student, or simply looking for ways to supplement your earnings, there are plenty of side gigs in Chicago that cater to different skill sets and interests. From flexible remote work to in-person opportunities, this guide explores the best side hustles in Chicago and how you can get started.
With a thriving transportation network, Chicago is a top city for rideshare and delivery services. If you have a car and enjoy driving, platforms like Uber, Lyft, DoorDash, and Instacart offer flexible earning opportunities.
💡 Pro Tip: Chicago’s busiest areas for rideshare include River North, Wrigleyville, and The Loop—especially on weekends and game days.
Chicago is a popular tourist destination, and with major events like Lollapalooza and The Chicago Marathon, short-term rentals are in high demand.
💡 Pro Tip: Wicker Park, Lincoln Park, and Downtown are some of the most profitable areas for short-term rentals in Chicago.
Chicagoans love their pets, but many busy professionals don’t have time to walk their dogs during the day. Services like Rover and Wag! make it easy to connect with pet owners.
💡 Pro Tip: Specializing in puppy training or overnight pet sitting can help you charge premium rates.
If you have marketable skills like graphic design, writing, or programming, freelancing offers a high-earning, flexible side hustle. Platforms like Fiverr, Upwork, and Toptal make it easy to find clients.
✔️ Digital marketing✔️ Content writing✔️ Web development✔️ Video editing and animation
💡 Pro Tip: Local businesses in Chicago often need social media management—offering affordable social media packages can be a lucrative niche.
With top universities like The University of Chicago and Northwestern, the city has a large student population in need of tutors.
💡 Pro Tip: Advertise your services at coffee shops near college campuses like Hyde Park and Evanston.
Chicago has a strong market for handmade and vintage items. If you’re skilled at making jewelry, candles, or thrift flipping, you can sell through Etsy, Facebook Marketplace, or local craft fairs.
💡 Pro Tip: Use Instagram and TikTok to showcase your products—Chicago shoppers love supporting local brands!
Health-conscious Chicagoans are always looking for personal trainers. If you're certified in fitness, you can offer private sessions or lead group classes in local parks.
💡 Pro Tip: Chicago’s fitness scene thrives in the summer—hosting outdoor boot camps can be a great way to attract new clients.
With its iconic skyline, Chicago is an excellent city for photographers and content creators.
💡 Pro Tip: Instagrammable spots like The Bean, The Chicago Riverwalk, and Navy Pier are perfect for offering photo sessions.
Chicago is full of side hustle opportunities that cater to various skills and interests. Whether you prefer flexible remote work, hands-on services, or passive income opportunities, the best side hustles in Chicago allow you to earn extra money on your terms.
