What Are the Best Side Hustles in Chicago and Los Angeles Ranked by Startup Cost, Flexibility, and Income?
Finding a profitable side hustle in Chicago can change your financial life. The same is true for anyone seeking a side hustle in Los Angeles. Both of these massive cities offer amazing options to earn extra cash. High living costs make extra income necessary for many working professionals.
We know how hard it is to choose the right path. Some gigs require too much money upfront. Other options take away all your free time. We want to help you find the perfect match.
The Side Hustle Comparison Table
The table below gives a quick summary of your options. It compares costs, flexibility, and average pay across both major cities.
Side Hustle
Primary City Focus
Startup Cost
Flexibility
Average Income
Online Tutoring
Chicago & Los Angeles
Under $20
High
$20 to $60 per hour
Pet Sitting
Chicago & Los Angeles
Under $30
Medium
$15 to $25 per hour
Digital Templates
Chicago & Los Angeles
$0
Very High
$100 to $1,500 monthly
App Delivery
Chicago & Los Angeles
$0 (With vehicle)
Very High
$18 to $28 per hour
Virtual Assistant
Chicago & Los Angeles
$0 (With laptop)
High
$20 to $50 per hour
Item Flipping
Chicago & Los Angeles
Variable
High
Variable profits
Lash Artistry
Chicago
Around $150
Medium
$40 to $80 per hour
Brand Management
Los Angeles
$0
High
$30 to $75 per hour
Event Photography
Chicago & Los Angeles
Variable (Camera)
Medium
$50 to $150 per hour
Low Startup Cost Hustles (Under $50 to Begin)
Want to earn extra money without spending much upfront? These side hustles use skills or tools you already have, making them easy and affordable to start.
1. Online Tutoring and Academic Coaching
With universities like the University of Chicago, Northwestern, UCLA, and USC, both cities have strong demand for tutors. All you need is a laptop, internet access, and expertise in a subject like math, science, or test prep. Platforms like Wyzant make it easy to connect with students. Many beginner tutors charge around $40 per hour, while test prep often pays even more.
2. Pet Sitting and Dog Walking
Busy pet owners across neighborhoods like Lincoln Park and West Hollywood often need reliable walkers and pet sitters. Create a profile on Rover or Wag, complete a background check, and start accepting bookings. Since no special equipment is required, you can build a steady client base with very little upfront cost.
3. Create and Sell Digital Templates
If you enjoy design, selling digital products can become a source of passive income. Use free tools like Canva to create planners, resumes, wedding invitations, or budget trackers, then sell them on marketplaces like Etsy. Since there's no inventory or shipping involved, you create each template once and can sell it repeatedly.
Maximum Flexibility Hustles (Work Whenever You Want)
If you need a side hustle that fits around your schedule, these options let you work whenever you have free time.
1. App-Based Delivery and Ridesharing
Apps like Uber and DoorDash let you choose when and how long you work. To maximize earnings, drive during busy periods such as evenings, weekends, or major sporting events. Popular areas include Wrigleyville in Chicago and Downtown Los Angeles during peak hours.
2. Digital Freelancing and Virtual Assistance
Remote freelancing gives you the freedom to work from anywhere while setting your own hours. Many businesses hire freelancers for email management, scheduling, customer support, writing, design, and administrative tasks. Platforms like Upwork and Fiverr make it easy to find clients and grow your income over time.
3. Flip Used Items
Buying and reselling secondhand items can be profitable in both cities. Look for deals on Facebook Marketplace, thrift stores, or garage sales, then clean or repair items before reselling them for a profit. You decide when to source inventory and manage sales, making this one of the most flexible side hustles available.
High-Income Potential Hustles (Premium Earnings)
These side hustles usually require training or specialized skills, but they can generate much higher earnings than entry-level gigs.
1. Lash Artist
Beauty services continue to see strong demand in both Chicago and Los Angeles. After completing a certification course, you can offer lash extension services at your own rates. Since clients return every few weeks for refills, this hustle can generate consistent repeat business and long-term income.
2. Social Media Management
Many local businesses need help managing their online presence but don't have time to do it themselves. You can create content, write captions, schedule posts, and manage accounts for restaurants, boutiques, gyms, and other small businesses. Charging a monthly retainer allows you to build recurring income with multiple clients.
3. Event and Portrait Photography
Chicago and Los Angeles offer countless scenic locations for portraits, family sessions, and brand photography. Build an online portfolio, promote your work on social media, and offer weekend photo sessions. A single shoot can generate several hundred dollars, especially as your experience and client base grow.
FAQs
What side hustle makes the most money?
Specialized services like certified lash artistry or local brand consulting make the most money. These roles require specific skills. They allow you to charge premium hourly rates compared to standard app delivery work.
How can I make an extra $1,000 a month?
You can earn an extra $1,000 monthly by tutoring online several hours each week. You can also achieve this goal by walking dogs daily or managing social media.
What is the easiest side hustle to start with no money?
The easiest zero-cost option is online tutoring or virtual assistance. You only need a laptop and your current knowledge. You do not have to buy inventory or pay heavy startup fees.
Do I need a business license for a side hustle?
It depends on your local city laws and your total earnings. Many independent contractors can start without a formal license. However, you should always check local regulations as your business grows larger.
Discover How Much You Can Earn Today
Are you ready to take control of your financial future? Finding the perfect side hustle can lift your financial burdens. Listen to our popular podcast, How Much Can I Make?, for deep insights. We interview real people who built amazing income streams from scratch. They share their exact numbers, struggles, and best tips for beginners. Listen to the show to get inspired for your own journey.
Visit our platform at How Much Can I Make? right now. Use our free resources to compare different business models today. Let us help you maximize your extra income safely and quickly!
