The Best Side Hustles to Make Cash in Chicago Quick & Easy

Chicago is a city known for its hustle. While the Midwest has a work ethic that’s unrivaled, Chicago, the region’s crown jewel goes above and beyond everyone when it comes to getting up early and staying up late. 

Along with the surrounding suburbs, Chicago is a place where it’s totally normal to meet folks with a side gig or two. It’s just the nature of the place thanks to its working-class roots – people will always work a few extra hours to have a spare couple of bucks to pay for their kid’s tee-ball camp in August. While a lot of folks have good-paying jobs, life gets expensive. 

Because of this, there’s a big market for figuring out a side hustle, something that’s not as mentally intensive as their nine to five. Whatever the need may be, paying down student loans or saving for retirement or finally finishing the basement, it’s essential to have extra cash to make moves with. 

When looking for a side hustle, think about these three things: 

  1. Growth
  2. Scheduling
  3. Money possibly earned

So, what can you do to make a couple of bucks? 

The 8 Best Side Hustles in Chicago

There’s the obvious answer with ridesharing. Some people love it, others hate it, but you can’t argue with the model of freedom brands like Lyft and Uber provide. If you’re looking to start working in the middle of the night and take a break whenever you want, why not? If you’re willing to grind, it’s feasible to make good money in a month, but you’ll have to put in some serious hours.

 1. Landscaping + snow plowing

Landscaping crews make substantial money, but it’s hard work. If you’re cool with getting your hands dirty and putting in some long hours, there’s money to be made. There are landscaping crews all over the Chicagoland area during the spring and summer months, but in the winter, snow plowing is seriously good money. The job is mostly overnight, but if you’re down with putting a plow on the front of your truck, the sky’s the limit. Some snow plowers can make up to $30 an hour. When Chicago gets clobbered with the inevitable snow attack, a season of snow plowing could definitely get some bills paid. 

2. Food delivery 

If you’re interested in using the car, but maybe not down with strangers sitting in the car, you’ve got another option: food delivery. A lot of people are crazy busy all day between work, their personal lives, kids, hobbies, and just about everything and the kitchen sink. Delivering food is a fantastic way to make side money because it’s just like Lyft because it’s on your clock. One setback is that once it gets late at night, there might be a slowdown, but since there are a lot of options for late-night food, there will always be hungry people who don’t want to leave their houses at 12:30 but still need that carne asada burrito. 

3. Teach what you know 

If you’re teaching, you’ve got the summer off. There are a lot of options to make money during the time when you’re off. There are plenty of local tutoring programs, but there are also a lot of ESL (English as a Second Language) programs teaching kids overseas. Most of these programs will work around your schedule. If you’re looking to work at night, the overseas tutoring is perfect.

All you’ll need is either relevant experience or a bachelor’s degree, and a computer with a camera and a mic. If you’ve got those things, you’re set. Look up VIPKid – they’re the original ESL platform with a ton of users. Plus, they’re always looking for teachers. 

4. Rent your car 

One of the easiest ways to make extra cash requires almost no crazy work on your part: rent out your car. If you’ve got a car you’re not using every day or just want passive income, check out Turo or Maven, both let users rent out their cars on their terms. You set the price and when the vehicle is available. Plus, the app covers insurance. 

5. Pick up all of the gigs 

If you’re looking to pick up side gigs, there’s always Adia. We help workers in every industry, from bartending to warehouses, distribution centers, sporting events, and everything in between. You set the hours and get paid every Friday. Plus, if you keep crushing it with jobs, there are all kinds of exclusive perks. If you’re a cook, you’re always going to want to cook, it’s in the blood, so why not pick up a few extra shifts when a black-tie event comes to town? If you’re a sports person, there’s a lot of stadiums in the city, and this could be your chance to work for the White Sox or the Blackhawks.

Plus, best of all if you’re concerned about tax time, Adia’s on-demand staffing puts all workers on a W2, so making that extra cash is a lot less stressful. 

6. Rent a room

Some people have extra space in their house, or maybe they have a secondary property, whatever the case – someone might want to use that space. There are apps for renting garage space, there’s always Airbnb for renting rooms, and even people renting their boat docks and backyards. If you’ve got the room, it might be something to consider. It all depends on how comfortable you are with people in your personal space – whether you’re using it or not. 

7. Become a flipper 

If you’re a passionate collector, there are a ton of resale shops, Goodwills, and garage sales all over the Chicago area. You could spend a weekend collecting records or oddities and putting them on Amazon and eBay, Instagram, or even Etsy. There’s always something on a table at a yard sale that someone a few states away wants. 

8. The side hustle mover or a handyman 

If you’ve got a truck, it’s easy to help people move. Or maybe if you don’t have a truck, you’re just strong and willing to lift heavy things. People are always ready to pay for help moving because it’s the worst. If you’re affordable and set realistic prices, there are plenty of weekends to make extra money by word of mouth. While not having a truck might cut into profits, it’s still a reliable way to make a few extra hundred a month. 

If you’re good with your hands, there’s always helping people to hang those tv’s, assembling new desks or installing a Nest to keep it cool. You could connect the services together, and that’s a car payment.

Find Work Fast with Adia 

How you make money is entirely up to you – there are plenty of ways in Chicago. It’s the city of the hustle. The town values hard work, and while they say New York is the city that never sleeps, Chicago is a city that never takes a break. What’s your favorite side hustle? As an on-demand staffing agency that provides Chicago staffing, we’d love to know. Drop us a comment or just check out the rest of the Adia blog. There’s a little something for everyone.

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