Looking for the best gig app in Chicago? You’re in the right place.
Chicago is a fast-paced city full of opportunities for gig workers. Whether you’re a student, a full-time employee wanting extra income, or a freelancer who loves flexible work, there’s something for everyone. But with so many gig apps out there, it can be hard to choose the right one. In this guide, we’ll help you find the best gig app in Chicago for your needs. We’ll cover top apps for delivery, ride-sharing, task-based gigs, and freelance jobs—so you can earn money on your schedule.
But with so many options, finding the best one can be tough. In this guide, we’ll show you the top gig apps in Chicago. These apps offer flexible hours, fair pay, and steady work. We’ll cover different types—like delivery, ride-sharing, task-based, and freelance jobs—so you can pick what suits you best.
Why the Gig Economy is Thriving in Chicago
Chicago is a hub of opportunity. With its dense population, active nightlife, massive tourism industry, and booming tech scene, it’s no wonder that gig apps are exploding in popularity. Here’s why gig work is booming:
- Flexibility: Gig apps allow you to work when and where you want.
- Diverse Industries: There’s a gig for everyone, from food delivery to graphic design.
- High Demand: With millions of residents and businesses, someone always needs a service done fast.
- Side Hustle Culture: Many Chicagoans use gig apps to earn extra income outside their 9-5 jobs.
Top 10 Best Gig Apps in Chicago
Uber & Uber Eats
Best for: Ride-sharing and food delivery
Payout: Weekly or instantly (with Instant Pay)
Uber is a household name in Chicago. Whether you drive people around or deliver food with Uber Eats, this app is a solid choice for flexible, high-demand gig work.
Pros:
- Huge customer base in Chicago
- Work during rush hours, events, or late nights for bonus pay
- Instant pay options are available
Cons:
- Car maintenance and fuel costs
- Peak hours can be stressful in downtown areas
DoorDash
Best for: Food delivery
Payout: Weekly or instantly via Fast Pay
DoorDash is another top app for food delivery in Chicago. It’s especially busy in neighbourhoods like Wicker Park, Lincoln Park, and the downtown Loop.
Pros:
- Set your schedule
- Great during lunch/dinner hours
- Moreover, tips can significantly increase earnings.
Cons:
- Income may vary based on location and time
- Requires your bike or car
Instacart
Best for: Grocery shopping and delivery
Payout: Weekly or instant cashout
If you’re good at grocery shopping, Instacart is a great gig app to consider. You’ll get orders from customers, shop for them, and deliver their groceries.
Pros:
- Higher payouts on larger orders
- Tips are common
- Flexible hours
Cons:
- Requires attention to detail
- Busy store environments
TaskRabbit
Best for: Odd jobs, handyman work, cleaning, furniture assembly
Payout: Daily payments available
TaskRabbit connects skilled gig workers to customers needing help with small tasks like furniture assembly, cleaning, moving, or even running errands.
Pros:
- Higher hourly pay than most apps
- Pick jobs based on your skills
- Strong user base in Chicago
Cons:
- Must pass a background check
- Competitive categories
Rover
Best for: Dog walking and pet sitting
Payout: 2 days after service completion
Love pets? Rover is perfect for dog lovers in Chicago. Walk dogs, pet sit, or even offer overnight care services.
Pros:
- Fun, low-stress work
- Set your rates
- Perfect for students or part-time workers
Cons:
- May require pet-care experience
- Income can be inconsistent
Thumbtack
Best for: Freelancers in trades (plumbers, electricians, photographers, etc.)
Payout: Based on your rates and bookings
If you have a professional skill or trade, Thumbtack helps you find clients near you in Chicago.
Pros:
- Great for skilled professionals
- Charge premium rates
- Regular work for top-rated pros
Cons:
- Must maintain a strong profile and reviews
- Competitive in popular services
Fiverr
Best for: Creative and digital freelance gigs (graphic design, writing, voice-over)
Payout: Cleared 14 days after order completion
Fiverr isn’t Chicago-specific, but many freelancers from the city make money here. You create a service (“gig”) and buyers place orders.
Pros:
- Global audience
- Flexible services and rates
- No need to leave home
Cons:
- Hard to stand out in popular niches
- Fiverr takes 20% commission
Upwork
Best for: Long-term freelance projects
Payout: Weekly or upon milestone completion
Upwork is ideal for more experienced professionals looking for remote gigs or project-based work in fields like software development, writing, design, and consulting.
Pros:
- Higher-paying clients
- Long-term opportunities
- Professional platform
Cons:
- The proposal system is competitive
- Charges service fees
Shipt
Best for: Grocery shopping and delivery
Payout: Weekly
Shipt, similar to Instacart, is available in the Chicago area and often partners with stores like Target. You shop and deliver groceries, and sometimes household items.
Pros:
- Easy entry
- Tips boost your pay
- Same-day scheduling
Cons:
- Must be efficient in stores
- Gas and vehicle wear and tear
GigSmart
Best for: On-demand, short-term labour jobs
Payout: Same day
GigSmart is rising fast in Chicago. You can pick up gigs like event staffing, manual labour, or delivery. It’s like TaskRabbit but broader.
Pros:
- High-paying, last-minute gigs
- Immediate payment
- Growing platform
Cons:
- Gig availability may vary
- Requires responsiveness
Tips to Succeed with Best Gig Apps in Chicago
Here are some quick tips to maximise your earnings:
- Multi-app: Use two or more apps (e.g., Uber + DoorDash) to increase your earning potential.
- Work Peak Hours: Lunch and dinner times are golden for delivery apps. Late-night work is well-suited for ride-sharing.
- Know Your Neighbourhoods: Wicker Park, Lincoln Park, River North, and Downtown have high demand.
- Track Expenses: Keep a log of mileage, fuel, and work-related expenses for tax deductions.
- Be Professional: Ratings matter. Always be polite, efficient, and reliable.
Emerging Gig Categories in Chicago
While the most popular gig apps fall under food delivery, ride-sharing, and freelance work, new gig categories are emerging in Chicago that cater to niche interests and skills. These platforms are creating even more flexibility and freedom for Chicagoans.
Fitness & Wellness Gigs
Apps like Soothe and Zeel allow licensed massage therapists and wellness professionals to offer at-home services. Chicago has a thriving wellness scene, especially in areas like River North and Lincoln Park, where people often request massages, yoga sessions, or guided meditation at home.
Home Services & Cleaning
Apps like Handy and TIDY help connect home cleaners and repair workers with homeowners. These are especially popular in family neighbourhoods like Lakeview or Bucktown. Many customers prefer freelancers to big service companies, creating demand for trustworthy gig workers.
Tutoring and Online Teaching
Platforms such as Wyzant and Preply enable Chicago residents to offer tutoring services both in-person and online. With many students seeking academic help post-pandemic, tutoring gigs in math, English, and test prep are highly valued.
Event-Based Gigs
Apps like PopBookings and Qwick focus on the hospitality and events sector. You can work as a bartender, event setup crew, or even check-in staff at conferences and trade shows. Chicago’s bustling convention and event space offers tons of potential here, especially at venues like McCormick Place or Navy Pier.
Safety Tips for Gig Workers in Chicago
While gig apps offer independence, it’s important to stay safe and smart while working in a big city like Chicago. Here are some crucial safety tips:
- Meet in public places when picking up tasks from strangers (especially with TaskRabbit or Thumbtack).
- Use dashcams or tracking apps if you’re driving for Uber or Lyft- it’s a small investment that protects you.
- Avoid late-night gigs alone in unfamiliar or poorly lit areas.
- Share your location with a trusted friend or family member while working.
- Wear branded gear (like DoorDash bags or Uber Eats shirts) to be easily identifiable, which can reduce risk and build customer trust.
Most gig platforms offer some level of insurance or protection, but it’s always a good idea to check the coverage and know your rights before you begin.
Legal & Financial Insights for Gig Workers in Chicago
As a gig worker in Chicago, you are classified as an independent contractor. This status offers you flexibility but also introduces certain responsibilities. Here’s a breakdown of the key considerations you should be aware of:
Tax Responsibilities
Unlike traditional employees, gig workers don’t have taxes automatically deducted from their earnings. It is essential to track your income, expenses, and business-related costs. You’ll need to file self-employment taxes during the tax season. Apps such as QuickBooks Self-Employed or Keeper can simplify this process by tracking expenses, mileage, and receipts.
Business Licenses and Permits
Depending on the service you provide, Chicago’s municipal regulations may require a business license. For example, individuals offering cleaning or handyman services through platforms like TaskRabbit might need specific permits. It’s advisable to consult with the City of Chicago’s Small Business Centre for current licensing requirements.
Insurance Considerations
For gig workers involved in deliveries or services that require visiting clients’ homes, liability insurance is highly recommended. While some gig platforms offer limited insurance, it often doesn’t cover all potential risks, particularly in the case of accidents or property damage. It’s best to explore additional coverage options to protect yourself.
Emerging Trends in Chicago’s Gig Economy (2025 and Beyond)
The gig economy is evolving, and Chicago is at the forefront of these changes. Here are a few key trends shaping the future of gig work:
Multi-Platform Integration
More gig workers are utilising platforms like Para or Gridwise to manage earnings across multiple apps. These tools allow workers to optimise their routes, track peak demand times, and compare gig income across different platforms, making the work more efficient and financially rewarding.
Artificial Intelligence in Gig Matching
Artificial intelligence (AI) and machine learning are now being used to match gig workers with jobs that align with their skills, availability, and preferences. This data-driven approach ensures that gig workers have access to better opportunities, enhancing both their income potential and job satisfaction.
Hybrid Gigs and Flexible Workspaces
The rise of hybrid gigs is a noticeable trend in Chicago’s gig economy. These roles combine both physical and remote work. For instance, a consultant might meet clients in person while also handling reports and administrative tasks online. This type of gig work provides even greater flexibility and the ability to balance various job types.
Gig Workers’ Rights and Unionisation
There’s growing support for stronger protections for gig workers in Chicago. Several organisations, such as the Gig Workers Collective, are advocating for improved rates, benefits, and legal safeguards for independent contractors. As the gig economy continues to expand, expect to see more initiatives aimed at improving the working conditions of gig workers. Learn more about how the gig economy works on Investopedia.
Checklist: Starting Your Gig Work in Chicago
To help you get started, here’s a practical checklist for entering the gig workforce in Chicago:
Essentials:
- A valid government-issued photo ID (driver’s license or state ID).
- A smartphone with internet access, as most gig platforms operate through mobile apps.
- A bank account or PayPal setup for payment receipt.
- A reliable vehicle or bicycle if your gig involves delivery or transportation.
- A clean background check which is often required by gig platforms.
- Your Social Security Number or Tax ID for tax reporting purposes.
Optional, But Recommended:
- A portable phone charger to keep your phone powered during long shifts.
- A GPS holder or mount to keep your phone secure and accessible while driving.
- A gig-tracking app to monitor your working hours, mileage, and earnings.
- A professional profile or resume, especially if you’re offering freelance services on platforms like Upwork or Fiverr.
The Gig Work Lifestyle in Chicago
One of the greatest advantages of gig work is its ability to fit into a wide variety of lifestyles. Whether you’re a college student at UIC or DePaul, a single parent, a retiree, or a creative freelancer, gig work offers flexibility and earning potential. In Chicago, this has proven to be a great way for people to:
- Discover new parts of the city while earning money.
- Avoid long commutes by working locally.
- Meet diverse people and gain valuable experiences.
- Balance work with family or personal projects.
Gig work empowers individuals to take control of their schedules, something that traditional 9-to-5 jobs often cannot offer.
Chicago’s Gig Economy Is Thriving
Chicago’s gig economy is more robust than ever. Whether you’re delivering food, offering consulting services, walking dogs, or assembling furniture, there’s a gig for everyone. The best part is that you don’t need a degree or a traditional boss — just download the right app, show up with enthusiasm, and start earning.
FAQs About Gig Apps in Chicago
What is the best gig app in Chicago?
DoorDash is often considered the best gig app in Chicago thanks to high demand, flexible hours, a strong tipping culture, and easy onboarding.
Which gig apps pay the most in Chicago?
Apps like TaskRabbit, Thumbtack, and Upwork typically offer higher hourly or project-based pay, especially if you have marketable skills.
Can I work for multiple gig apps at once?
Yes! Many gig workers in Chicago combine apps like Uber + DoorDash or TaskRabbit + Thumbtack to maximise earnings.
Do I need a car for gig work in Chicago?
Not always. Apps like DoorDash, Uber Eats, and Instacart support bike and scooter deliveries. Remote freelance platforms like Fiverr and Upwork don’t require transportation at all.
Are gig apps safe to use in Chicago?
Yes, most are safe. Follow best practices like meeting in public places, using a dashcam, and sharing your live location with a friend or family member.
How do gig workers get paid?
Most apps pay weekly. Some, like Uber, DoorDash, and GigSmart, offer instant cashouts with a small transaction fee.
What are the busiest areas for gig work in Chicago?
Top hotspots include Downtown, River North, Wicker Park, and Lincoln Park, especially during lunch, dinner, and event hours.
What’s better for beginners: delivery or freelance gigs?
Delivery gigs (like DoorDash and Instacart) are easier to start. Freelance platforms need skills and a strong portfolio, but they can pay more in the long run.
What’s the best gig app in Chicago for pet lovers?
Rover is a great option for dog walking and pet sitting, especially in residential neighbourhoods.
New to gig work? Check out our Beginner’s Guide to Gig Work to get started.
