The Best Side Hustles in Chicago for 2026

Chicago is a city full of people who work hard, dream bigger, and always look for ways to make life a little easier. Rents go up, groceries feel higher than ever, and many people want extra money without taking on a second job that drains all their energy. This is why side hustlers in Chicago have become more creative each year. Some want a great way to make extra cash while keeping their full time job. Others want something flexible they can grow into a full time career. And some are simply looking for a little extra income that fits into their spare time or free time.

If you are reading this, you might be one of those job seekers who is tired of looking at a long list of search options that do not actually improve your quality of life. You might have searched the top side hustles, or maybe you clicked through job postings on every platform possible. You may have even read through Linkedin’s user agreement without realizing it because you were scrolling so quickly.

What people really want is something simple. A side job that pays well. A type of work that does not require much time to start. A great side hustle with low startup cost. And ideally something that allows you to set your own rates, your own prices, and your own schedule.

This is why lash artists in Chicago are quietly becoming some of the highest earning side hustlers in the city. Before we talk about why, let’s walk through the best side hustles in Chicago for 2026 so you can see how they compare.

1. Delivery Driving and Food Delivery

Food delivery and courier apps always attract new job seekers because you can start quickly once you pass a background check and set up a bank account for eligible direct deposit. Delivery riders see peak hours in the evenings or weekends, which can be a great time to earn extra bucks or extra cash.

However, this type of work can depend heavily on weather, traffic, and slow nights. Chicago winters can make this option less appealing for some. It is an easy way to earn but it may not be something you want long term.

2. Virtual Assistant Work

A virtual assistant helps busy people or small businesses with daily tasks like scheduling, emails, documents, social media posts, and customer support. This is a great side hustle if you enjoy organization and communication.

However, you often have to work during the same hours as your client which may limit your flexible schedule. Some VA roles require you to learn new skills which is not a bad thing, but it is important to find the right subject area. You can set your own rates, which is helpful, but this field can be competitive.

3. Freelancing in Video Editing, Digital Marketing, or Graphic Design

This category continues to grow because local businesses always need help with branding, educational content, marketing campaigns, or visuals. For people who enjoy creating, these side gigs can turn into a full time career.

However, many beginners feel overwhelmed because these fields can require online courses, past examples, or experience. The start up costs can be low, which is a plus, but it can take time to build a strong client base.

4. Selling Products on an Online Store or Facebook Marketplace

Chicago residents love finding deals and unique items on Facebook Marketplace. It can be a great way to earn extra money without much commitment. You can also start an online store with little money upfront if you want to sell digital products or handmade items.

The challenge is that income can go up and down. It also depends on how much time you want to put into listings, packaging, and customer service.

5. Pet Sitting and Dog Walking

Pet owners in Chicago are willing to pay for someone they trust. This side job can feel peaceful and enjoyable if you love animals. You can set your own prices and choose which clients you accept.

The challenge is that schedules may conflict with your day job and you may need to be available early mornings or evenings.

6. Becoming a Lash Artist

The Side Hustle That Out Earns All of the Above!

Out of every option available in 2026, becoming a lash artist consistently earns the most while still offering a flexible schedule, very low startup cost, and the chance to build a full time career if you want one.

Here is why lash artists in Chicago are making more than most other side hustlers right now.

Lash Artists Earn Higher Rates From the Start

When you complete eyelash extension training and become a certified lash artist, you are able to charge rates that are significantly higher than delivery drivers, virtual assistants, freelancers, or retail sellers. Even as a beginner, Chicago lash artists can earn more in one classic set appointment than many people make in a full shift at their side job.

Clients pay well because eyelash extensions are in high demand and they require a skilled service provider. Once you understand lash application and techniques, you can offer a service people want again and again.

Lash Artists Build a Steady Flow of Potential Clients

The great thing about lashes is that clients come back every two to four weeks. Unlike delivery apps or graphic design projects that come and go, lash artistry creates repeat business. You are not constantly hunting for new clients because your regulars naturally return.

Chicago is a beauty loving city. People want to look put together for live events, weekends, work, and daily life. Lash artistry fits perfectly here.

The Work Fits Into Any Financial Situation or Schedule

Lash artists do not need much time to get started. You can take clients in your spare time, evenings, or weekends. You can keep your day job and still earn a great side income with just a few clients a week.

Many of our students say that lashing gave them the freedom to leave a second job that drained them. Others built a strong enough client base to eventually turn their side gig into a main gig.

Low Start Up Costs Compared to Other Side Hustles

Delivery drivers need a car, gas, parking, and constant maintenance. Freelancers sometimes need expensive software. Online sellers need inventory.

A lash artist needs a small kit, which is affordable and lasts for many clients. The income you generate quickly covers that initial investment.

You Can Work From Anywhere and Set Your Own Rates

As a lash artist, you choose your own prices. You choose how many clients you accept and which days you work. You choose what type of work environment fits your quality of life. Some work from home. Some rent a small studio. Some work inside larger beauty spaces.

The freedom is one of the biggest reasons people switch from side hustles to lash artistry.

Why Lucylu Lash Academy Is the Top Choice in Chicago for 2026

If you want to start lashing the right way, you need skilled instructors, hands on practice, and real guidance. Lucylu Lash Academy has become one of the most respected training programs in the city because we teach you everything you need to begin earning as soon as you complete the course.

We give you live model practice, hands on training, ongoing support, and a learning environment that feels encouraging and welcoming. We show you how to attract potential clients, how to price your services, how to understand your financial situation, and how to grow at your own pace.

The moment you walk in, you can feel that this is not a typical classroom. It is filled with beauty professionals who want you to succeed. Our students often say the program changed their life because lashing became their easiest and most profitable way to make extra income.

If you want to enroll or want to talk about which course fits your goals, you can call or text 773 870 2816 and we will guide you with honesty and clarity.

Which Chicago Side Hustle Pays the Most in 2026

If your goal is to earn extra money quickly while keeping your full time job, nothing compares to becoming a certified lash artist. The income is strong, the demand is high, and the freedom feels unmatched.

If you want a great side hustle that can turn into something bigger, or if you simply want extra cash without working yourself to exhaustion, lashing is one of the best choices you can make.

Lucylu Lash Academy can train you from the ground up and support you every step of the way. You are not doing this alone.

Book your training today so you can start earning more and living better in 2026. And remember, you can always call or text 773 870 2816 with any questions.