14 Flexible Side Gigs to Help You Make More Money in the Windy City

Carmen Mandato/ The Penny Hoarder


So you live in one of the largest cities in the country… the Windy City.

The good news is it’s not New York City or Los Angeles. The bad news is it’s still expensive.

The median rent for a one-bedroom apartment in Chicago is $1,590, according to Zillow data. And the average income of those who rent these one-bedrooms is about $33,452 a year. Factor in utilities and that means 62% of your income is going toward housing, according to a Penny Hoarder analysis of Census microdata.

Then consider food, another necessity. You're spending an extra two pennies for every dollar you'd spend in other U.S. cities, according to regional price data from the U.S. Bureau of Economic Analysis.

Those pennies add up!

How to Make Extra Money in Chicago

If you need a little income boost, don’t be down. There are tons of flexible side jobs available in Chicago.

1. Get Paid to Drink Beer

Neil Callaghan, an advanced level cicerone, currently working at Cigar City Brewing
Carmen Mandato/The Penny Hoarder

Chicago: We see you with all your breweries.

If you enjoy hoppin’ around town and trying out what’s on tap, consider becoming a “Secret Hopper.” It’s like secret shopping — but for breweries.

The company is looking for detail-oriented beer-drinkers to hop around to different breweries and objectively rate and review their experiences. Penny Hoarder writer Tyler Omoth gave the gig a try. He spent $16 on his visit to a local brewery. Secret Hopper paid him $20 via PayPal within a few days.

So, no, you’re not going to get rich, but you will get free beer, and that makes us hoppy.

All you have to do is sign up, then Secret Hopper contacts you when you’re needed.

2. List Your Spare Room for the Night (Especially During Lollapalooza)

airbnb listing in chicago
Photo courtesy of Airbnb

Have a spare room? Might as well try to earn some money by listing it on Airbnb.

If you’re a good host with a desirable space, you could add hundreds, even thousands, of dollars to your savings account with Airbnb.

And there's no reason you can't be creative. We found someone listing a train car over in Plano, Illinois!

A few simple steps can make the difference between a great experience and a less-than-satisfactory one.

Here are some tips:

  • Make your space available during high-demand times in your area. Think: concerts, festivals (ahem, Lolla), conventions and sporting events. Chicago has plenty of those!
  • Be a good host, and stock your place with the toiletries you’d expect at a hotel — toilet paper, soap and towels.
  • Be personable. A lot of travelers turn to Airbnb for the personal touch they won’t find at commercial properties.

Here’s the link to sign up as an Airbnb host.

(Hosting laws vary from city to city. Please understand the rules and regulations applicable to your city and listing.)

3. Find a Part-Time Work-From-Home Job

hands typing on a laptop
Chris Zuppa/The Penny Hoarder

If you already have a full-time job, finding something on the side that’s relatively flexible can be challenging — especially if you don’t want to go into an office.

A part-time work-from-home job could be the perfect solution.

Start by searching ZipRecruiter. When you click here to search, ZipRecruiter sends you to a list of geo-tailored, work-from-home job openings. (Because, yes, even some work-from-home jobs have location restrictions.)

Peruse the work-from-home opportunities available in Chicago.

4. Rent out Your Car When You Take the ‘L' to Work

Carmen Mandato/ The Penny Hoarder

Want to make money with your car, but not keen on playing taxi? Let folks rent your car when you’re not using it.

OK, that sounds a little scary, but it doesn’t have to be.

With the Getaround app, you can safely rent out your car to people in your community and neighborhood. The company insures your car for each trip, offers 24/7 roadside assistance and screens drivers for a safe driving record.

Getaround says users can make up to $10,000 a year. That’ll probably cover your car payments!

Learn more about Getaround — so you can “Getaround” having to work overtime each week.

5. Stay Inside and Hide From the Wind

Two young women eating popcorn, wrapped in a blanket and watching a movie.
shironosov/Getty Images

Surveys aren't our favorite way to make money, but if you're just binging on Netflix to avoid the snow or stinging winds outside, why not click a couple buttons and earn a few bucks?

We’ve tried a lot of paid survey sites, but some of the best we’ve found are Inbox DollarsOpinion Outpost and MyPoints.

6. Play Professional Line Sitter

people standing in line
TommL/Getty Images

You’ve got the big tourist attractions: the Willis Tower Skydeck and 360 Chicago. Then there are the lines that form for novelty foods, including Garrett Popcorn Shops and the Nutella Cafe.

You’ll also find lines outside The Chicago Theatre and Second City — even outside the museums.

This is your money-making opportunity, Chicago locals. Step up your game and become a professional line sitter.

Back in 2016 we interviewed Robert Samuel, a professional line sitter who says he charges $25 for the first hour in line and $10 for each subsequent hour. He’s even started a New York City-based business with line sitters who’ve stood in line for “Hamilton” tickets, cronuts and the latest iPhone releases.

If you’re not sure where to start in Chicago, Samuel recommends offering your services on Craigslist or TaskRabbit.

7. Drive Tourists to the Nearest Giordano’s

Alexa Vincent navigates her mobile apps, including
Chris Zuppa/The Penny Hoarder

If you’re looking for a way to earn extra money while choosing  your own schedule, driving with Lyft could be the perfect solution.

When you sign up to become a Lyft driver, you’ll get to drive (and make money) whenever you want.

To be eligible, you’ll need to be at least 21 years old with a year of driving experience, pass a background check, and own a car made in 2007 or later.

Check out how former Chicago news anchor Anthony Ponce quit his job to drive with Lyft (and started a podcast).

8. Set Your Own Hours When You Start Your Own Business

Amanda Meisner runs errands in downtown Chicago
Carmen Mandato/The Penny Hoarder

Have you ever considered starting your own business? You could just set your own hours — and not answer to anyone else.

If you’re not sure where to start, we found an online course that’ll guide you through the process.

If you’re interested in becoming a work-from-home bookkeeper, try Bookkeeper Business Launch — no CPA required. You just need some decent computer skills and a passion for helping business owners.

Daniel Honan took the course, and within 10 weeks he’d launched his bookkeeping business for painters. The opportunity has allowed him to work from home and spend more time with his wife — without compromising his income.

If you’re interested, check out the free starter course.

9. Grab a Gig at Wrigley Field

Wrigley Field on Fathers Day
jleathers/Getty Images

If you’re looking for hourly gigs, sign up for Shiftgig. Headquartered in Chicago, the platform connects workers to gigs in a number of industries, including food service, hospitality, retail and customer service.

“We are always working with some of the biggest venues in town,” Mike Flickinger, the general manager of Shiftgig’s Chicago office, said in a 2016 interview. “We have had a significant presence working with partners at major sporting events, like the White Sox, Cubs and Bears stadiums.”

Interested? Read about one Penny Hoarder’s experience using the platform.

10. Do the Cupid Shuffle

Photo of a lovely couple during the dinner party with friends, in an outdoors bistro
AleksandarNakic/Getty Images

When you think of a matchmaker, you might think of a cartoon cupid character or even some type of genie in a bottle. The notion seems unreal — that someone could actually set you up with your soulmate. And, no, we’re not talking about Tinder.

Tawkify employs a team of matchmakers across the U.S. (Chicago makes the list!) to match hopeless romantics — and it’s always looking for new members to join.

You don’t necessarily need a background in matchmaking. Team members have included lawyers, life coaches, entrepreneurs, teachers and even writers. Some matchmakers have made up to $50,000 a year working part time.

11. Sell Your iPhone Photos

woman taking photographs with her mobile phone in the hall of the Union train station in Chicago, Illinois.
Boogich/Getty Images

Chicago is a captivating city, so we don’t blame you if you’re constantly snapping photos around town — even as a local.

No longer is this pointless, though. (Or just for Instagram.) You can sell your iPhone photos through an app called Foap.

It’s super easy to use: Download the app, and upload your photos. When someone wants to purchase your photo, you’ll get 50% of the profit. (Foap gets the other 50%.)

Say someone buys one of your photos for $10. You pocket $5. If the photo sells 20 times, for example, you could end up with $100.

It only takes about five minutes to upload a photo. If you want all the details, we’ve put together a Foap rundown.

12. Beef up Your Acting Skills

Hospital Doctor With Digital Tablet Talks To Male Patient
monkeybusinessimages/Getty Images

If you have experience in acting, sign up to play a standardized patient.

The University of Illinois College of Medicine is typically looking for standardized patients, or SPs. These are actors who play the role of a patient or family member so medical students can practice their bedside manner.

The University of Chicago outlines everything you need to know on its application page.

Other facilities hire SPs in Chicago periodically, too. For example, at the time we wrote this article the National Board of Osteopathic Medical Examiners had open part-time SP positions. The site said pay starts at $18 an hour. For more information, check out its employment page.

You can always search SP positions on Indeed, too.

Heck, playing an SP might be your big break. Next thing you know, you’re featured on “Chicago Med” or “Chicago P.D.”

13. Deliver Chicago Hot Dogs

Carmen Mandato/ The Penny Hoarder

Ahhh, the sweet smell of takeout stinking up your car.

OK, it might not be the most appealing thing in the world — you might want to crack a few windows, depending on the type of cuisine you’re delivering — but Uber Eats offers flexible food-delivery opportunities.

Drivers are paid a pick-up fee, for the distance traveled and a drop-off fee. Uber takes a service fee. Delivery partners can cash out up to five times a day with instant pay.

Requirements may vary by location. Here are the basics…

  • Be at least 19 years old if delivering by car.
  • Deliver via car (must be a 1997 or newer with at least two doors), bike, scooter or foot depending on your area.
  • Pass a background check.
  • Have a valid driver’s license and insurance (if you deliver by car or scooter).

14. Get Paid While You Watch the Cubs Game

Not sure what to do during the seventh-inning stretch? Watch videos! (We know you were heading to YouTube, anyway…)

InboxDollars lets you actually get paid to watch videos online. The site hosts a ton of stuff to watch, including cooking, entertainment, news and health shows. The shows are sponsored by brands that need to get them in front of as many eyeballs as possible. Every time you watch one, InboxDollars will credit your account with a little bit of cash.

Carson Kohler ([email protected]) is a staff writer at The Penny Hoarder. She visited Chicago last year and could totally see herself living there — at least until the first snowstorm of the season. Then she’d move back to Florida.

Penny Hoarder data journalist Alex Mahadevan contributed to this article.

Do you think this article might help you put more money in your pocket?Thumbs UpThumbs Down