10 Side Hustles to Try in Chicago to Make Extra Cash

So many side hustles in Chicago end up feeling like a scam because you spend so much time making so little money but trust us when we say these options do a solid job of making you cash (and no, they aren’t pyramid-schemes).

Here are all the top side hustles you can score in Chicago to pick up some extra cash after your day job.


Best Pizza Places in Chicago
Photo Credit: Uno Instagram

View the Best Pizza Restaurants in Chicago, Ranked

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View the Best Pizza Places in Chicago



Photo Credit: Uber Facebook

Ride Sharing

Uber and Lyft are excellent side jobs in the city that allow you to pick up tips while you’re cruising around or headed towards a destination. Chicago is loaded with people looking for rides, so as long as you have a few hours to work with, or even just one, you can spend that time taking people around town and turn off the system whenever you want. On average, Uber drivers in the city make between $15 to $16 an hour. Not bad for just giving the ol’ wheels a spin!

Uber Eats
Photo Credit: Uber Facebook

Food Delivery

There are plenty of people who are way too lazy to leave their house and walk the three blocks it takes to pick up a pizza from that place on the corner. Heck, sometimes folks won’t even walk downstairs to the restaurant they live above to grab a bite to eat. If you’re looking for a side hustle in Chicago, UberEats gives you the opportunity to deliver food to these families in Chicago. You are able to choose which orders you pick up and when. Yeah, your car might be full of strange, new smells, but on the bright side, your pockets will be full of new cash.

Windy City Dog Walkers
Photo Credit: Windy City Dog Walkers Facebook

Dog Walking

Wag! and Windy City Dog Walkers are both perfect if you spend most of your time walking the streets of your neighborhood. When you’ve got some time on your hands, open one of these apps and see who’s in need of a dog-walker. They even have open slots where you can stake your claim on scheduled walks ahead of time, so it’s always guaranteed you’ll make some cash. The added benefit of getting some exercise is just a small perk. Getting to hang out with cute, furry friends is the bigger perk.

Photo Credit: TaskRabbit Facebook

Manual Labor

Feeling handy? (Hey now, we said ‘hand’-y, not ‘hands’-y!) You can help someone move into or out of their apartment, help mount a TV, or even reorganize their space with TaskRabbit. Users can easily book appointments with people in their area, including you, even if you have no prior experience. You can also use Schlep to sign up for specific moving services if that’s your area of expertise. If you’ve got the hustle and the muscle for it, this is an easy way to earn some extra pocket cash.



Work for a Local Business

Remember that barista job you landed at Starbucks when you were sixteen? Never thought it’d come in handy again, did you? Well, now it has. Help out your neighbors when you sign up for Shiftgig, an easy way pick up a side hustle in Chicago to rake in cash based on your prior experience. 

Photo Credit: UrbanSitter Facebook


Yes, it’s glorified babysitting, but you can get some serious bucks from these desperate and busy Chicago parents looking for someone they can trust. Some great sites to sign up on are UrbanSitter and Care.com. All they’ll ask for is a background check to make sure you’re not a murderer and you’re in! (We are not liable for any diaper-related accidents.)

Lisa Beauty
Photo Credit: Lisa Facebook

Beauty Services

Went to beauty school but decided to pursue something else? Get back to your real passion by opening your own little home shop with LisaYou can give people the royal treatment on your terms, whether you do hair, nails, or massages! Determine your own rates, set your schedule, and pick up clients when it conveniences you. It’s that easy to make some extra cash doing something you really love while also helping someone else feel confident and comforted!

Photo Credit: Airbnb Facebook

Rent Out Your Place

Going away for the weekend? Sign up with Airbnb to let guests from out of town stay at your place. You can determine the pricing, the house rules, the interaction, and everything in between, so you’re completely comfortable the whole time. It’s a great way to earn extra cash without letting the space you pay for end up going to waste.


Pay Your Selfie

Take Some Selfies

Not as creepy as it sounds. Businesses are constantly looking for people to promote their platform, so if you can take a selfie that incorporates some of their values—like wearing their logo or displaying their product—all you have to do is tag their handle on the Pay Your Selfie app and wait for the cash to roll in. With cameras in most phones these days, this moneymaker is literally just sitting in your pocket and waiting for you to make that green.


Get a Refund

There’s this sweet new app that keeps track of all your purchases and makes note of when their prices fall. If you paid more at one time than it costs now, Paribus will refund you that cash in a heartbeat. So go ahead, get that sweater that’s not even a little bit on sale, and never overpay again! There’s seriously nothing better than knowing you’ll always get the best price on something, even if you didn’t pay it upfront!


Pro Tip!: Successful people have multiple forms of income. Why not try out a few of these and use them interchangeably? (i.e. keep both the Uber and Lyft app open while you search for rides, so you can get that cash quicker than ever)


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