The Best Ways to Earn Extra Money in Chicago (2023 Update)

Living in a bustling city like Chicago, many individuals are on the lookout for lucrative side hustles and freelancing opportunities to supplement their income. With the increasing demand for flexible work options, there has never been a better time to explore various ways to earn extra money by capitalizing on your unique skills and resources.

In this article, we will discuss some of the best ways to earn extra money through side hustles and freelancing in the Windy City. From rideshare driving and home-sharing to freelance writing and selling handmade crafts, there’s a diverse range of opportunities that cater to different interests, skill sets, and schedules, allowing you to make the most of your free time and maximize your earning potential.

Side Hustles in the Gig Economy

Rideshare Driving

Rideshare driving is a popular side hustle in Chicago, where platforms like Lyft and Uber connect drivers with passengers needing rides. This option is ideal for those with a reliable vehicle and flexible schedule. Earnings depend on factors like time spent driving and number of completed rides.

Food Delivery

Food delivery services like DoorDash, GrubHub, and Uber Eats have gained popularity in recent years. These platforms allow people with a car or bike to earn money by delivering restaurant orders to customers’ homes. Tips and surge pricing can boost earnings, and flexible hours allow for a customizable work schedule.

Pet Services

Providing pet services such as dog walking, pet sitting, and boarding, can be an ideal side hustle for animal lovers. Websites like Rover and Wag connect pet owners with service providers in the area. Insurance and background checks are usually required, and rates can vary depending on location, experience, and specific services offered.

Task-Based Services

Task-based service platforms, like TaskRabbit, allow users to offer various services, ranging from furniture assembly to home repairs. Freelancers set their rates, and availability on the platform, making it a versatile option for those looking to monetize their skills.

PlatformServices OfferedEarning Potential
Lyft/UberRideshare DrivingVaries on factors such as time and number of rides
DoorDash/GrubHub/Uber EatsFood DeliveryDepends on order volume and tips
Rover/WagPet ServicesBased on location, experience, and services
TaskRabbitTask-Based ServicesFreelancers set their own rates

Local Niche Opportunities

Seasonal Jobs

Seasonal jobs in Chicago offer various opportunities across different industries. Some options include:

  • Working at farmers markets
  • Summer camp positions
  • Park district jobs
  • Retail positions during the holiday season

Seasonal jobs often require a short-term commitment and provide a great way to earn extra income while gaining valuable experience and networking opportunities.

Event Staffing

Chicago hosts numerous events throughout the year, creating a demand for event staff. Some positions to consider include:

  • Usher at a theater or concert venue
  • Bartender or server at corporate events or weddings
  • Event setup and tear-down crew

Working as event staff is a flexible way to generate extra income based on your schedule and interest in the event industry.

Tutoring and Teaching

Sharing your knowledge and expertise through tutoring or teaching can be a lucrative and fulfilling side hustle in Chicago. Some opportunities include:

  • Offering music or language lessons
  • Helping students prepare for standardized tests
  • Teaching a fitness or art class

Platforms like Varsity Tutors, TakeLessons, and Thumbtack connect skilled individuals with clients in need of tutoring or instruction, making it easier to find work in this field.

Tour Guiding

As a city with rich cultural and architectural diversity, Chicago has a thriving tourism industry. Becoming a tour guide is a unique way to earn extra money while showcasing your passion for the city. Some options include:

  • Working as a docent at a museum or historical site
  • Leading architecture or river cruises
  • Conducting food or neighborhood tours

To become a tour guide, you’ll need a thorough knowledge of Chicago’s history and attractions and excellent communication skills to engage with tour participants.

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