Chicago is home to more than 2.7 million residents and is considered the most populated city in Illinois State.

As a matter of fact, Chicago ranks third in the United States as one of the most populated cities.

Chicago’s humble beginnings as a small trading mouth situated on the delta of the Chicago River.

Since that time in the 1880s, Chicago has grown substantially into one of the United States of America’s greatest metropolises.

It is a hub of commerce, telecommunications, industry, technology, transportation, and finance not only in Illinois, but across the nation.

The history of Chicago is not only rich, but interesting and unique.

Some of the most interesting things that happened in this city are the first skyscraper, the first automated bread factory, and the first mail order business.

It is known as a city where innovation and diversity are welcome and encouraged.

It is a city where many people have achieved the American Dream, as you can.

The location of Chicago is ideal for trade because it is somewhat central to the East and West, but the westside is where most trade happens.

Business Opportunities in Chicago, Illinois

Here are some small business ideas in Chicago, Illinois to help you brainstorm about what kind of small business you want to start in The Windy City.

1. Catering Business 

Catering Small Business Ideas in Chicago

This metropolis is full of events and festivals, which means lots of food and beverages flowing.

While the catering business opportunity may seem saturated on the surface, looking deeper into it, more caterers are needed to meet the demand of this widely populated city.

The good news is that you don’t need any formal qualifications to start a catering business.

All you need is dedication and a professional attitude to thrive. 

2. Event Planning & Management 

Catering is only one aspect of the event scene in Chicago.

Another high-demand service is event planning and management.

So many things are always happening in Chicago, online and offline (virtual events), that an experienced, dedicated professional with expertise in this area could build an empire.

There is a lot of potential in this opportunity. 

3. Food & Beverage Truck

Food & Beverage Truck Small Business Ideas in Chicago

Humans love their food.

A food and beverage truck with the proper placement can be fruitful financially.

With a mobile business like this, you can move your business around the city to get the most ROI (return on investment) from it.

You may be able to find a retiring business that is selling their food truck and reduce your investment costs.

As far as businesses go, there is little investment involved. 

4. Diner or Eatery 

Locals and tourists alike enjoy locally-owned and operated eateries like a diner.

With an affordable investment, you can create a diner that will have those local and out-of-town foodies flocking to your eatery to enjoy your offerings.

Take a look around the area where you want to start a diner and research what kind of cuisine (something different) would fit that target market.

Or choose your target market and cuisine, then seek a viable location for it.

Humans not only love their food, they love trying new things.

5. Organic Foods Business

Organic foods are popular among the health-conscious target segment.

It is still relatively new to the market, but it is innovative and Chicagoans like innovation.

Fast food, conventional restaurants, and other eateries do not offer the healthy foods that healthy people want.

Many of the wealthier people in this city are happy to buy organic foods. 

6. Tour Guide Agency

Tour Guide Small Business Ideas in Chicago

Are you a Chicago native or have you lived there for a long time?

Maybe you know all the hotspots, best discounts, or have a network to draw off of to start your own tour guide agency.

Chicago being a big and busy city has inhabitants and tourists who don’t want to waste time with tickets, hotels, and transportation.

You can be their guide to easily navigate the city, get the best reservations for food, lodging, transportation, events, and other travel-related solutions they need.

With around 50 million tourists visiting this huge metropolis every year, you could grab part of that revenue in your business if you leverage it well.

7. Rental Guests 

Does your house have a spare room or two? If so, you can turn those rooms into revenue-generating rentals.

Some people enjoy the comfort of home away from home, which is how you would begin to leverage the potential of this idea.

You may be able to get some regular business travelers as well as tourists who like the idea of having a bedroom in a house rather than a hotel.

Add a meal, like breakfast to the mix and you will essentially be a bed and breakfast. 

8. Hotel/Hostel  

Hotels, motels, hostels, etc. make up a large portion of Chicago tourist reservations.

People travel to Chicago for business, personal, and for educational purposes.

A hotel with extended stay rates would do well in this city.

If you already have a building sitting idle in the middle of the city and close to institutes of higher learning, you have the potential of having a lucrative business.

Foreigners and Americans who must live in Chicago for a period of time where it is not worth renting an apartment or buying a house, will flock to your hostel.

Reasonable rates and superior services are keys to success.

9. Taxi/Transportation Service

Transportation Service Small Business Ideas in Chicago

Chicago is more than just a city.

It features 237 square miles of land that requires reliable transportation.

You may think that there are already plenty of taxi or rideshare services in the city, but with such a large population and tourists, transportation services are still high in demand.

Remember to be approachable, friendly, professional, and user-friendly to your fares.

10. Yacht Rentals

As mentioned earlier, Chicago is situated on the Chicago River, but it also has access to the Michigan River.

With the wealthy population being quite large here, yachts of all sizes can be found floating these navigable waterways.

If you own a yacht (or a fleet of yachts) turn them into money-generating rentals when you’re not using them to increase your income. 

11. Job Placement Agency

The job market in a large metropolis can be overwhelming to newcomers or natives of Chicago when they are out of work.

Not everyone has a network of friends, family, or coworkers with ties to help them obtain work.

That is where job placement agencies are helpful.

You can take the overwhelming task of finding a job to a manageable level for people seeking employment.

By charging commissions in return for your services (hard work), you can create a great revenue with almost no investment. 

12. Software Training Business

Software Training Small Business Ideas in Chicago

If you have expertise and skills suited to specialized software, there is plenty of money to be made in starting your own training business.

Big to small businesses often require software for their systems that they simply don’t understand how to use are those who are not using it to its full potential.

You could help with your skills and knowledge to use their software more efficiently.

You can offer one-on-one training (virtually or in person) or you can provide training videos to groups, train in groups/teams.

Either way, this is a lucrative business idea.

Even though they can find free online tutorials, one-on-one training (face-to-face or virtual) can make the difference between mediocre and superior use of their software.

Some applications where this might prove useful includes Auto CAD, SAP, Oracle, and Adobe Photoshop and Creative Cloud. 

13. Real Estate Consultant

Money is always in real estate in large cities.

If you know how things work in real estate, you can start a business consulting with buyers and sellers then put them together for a commission.

This idea is not about becoming a real estate agent.

It’s more of a finder’s business where you connect buyers and sellers.

Make sure you check into the local laws and regulations before engaging in this industry.

It may require that you be an agent or retired agent with an active license.

14. Sports Coaching 

Chicago is a sporting city.

They are home to several sports teams (baseball, football, basketball, etc.).

This city happened to be a candidate for the Summer Olympics in 2016, but lost it to Rio de Janeiro.

The city is full of energetic and ambitious youth who need some coaching to reach their full potential.

If you are a sports professional, coaching is your way into a lucrative income with this business.

15. Cleaning Service

cleaning service Small Business Ideas in Chicago

Who has time to clean their homes or offices in Chicago?

By the time they commute to work and back, at least two hours are wasted on the road for most of them.

Besides that, they work an 8-hour or more day job, which leaves them little to no time for cleaning.

Not only is there potential in residential house and apartment cleaning, but the commercial and industrial sectors could be potential winners in this metropolis.

Be professional.

Be knowledgeable and provide excellent cleaning services to be successful.

16. Dry-Cleaners

The working class of Chicago are not only too busy to clean, but chores like taking and picking up their dry cleaning get lost in the shuffle.

These very people would love to have a service to drop off and pick up their dry cleaning according to their instructions.

Be reliable, dependable, and good with people to be successful. 

17. Elder Care Service

More and more people are choosing to stay home in their older years.

Chicago has an elder of those 65 and older population of about 10% who require care, attention, and companionship.

Starting a business to care for our senior citizens is not only an income-producing job for you, but a labor of love that the families will appreciate.

Patience, compassion, and a positive caregiver attitude is needed to be successful.

18. Babysitting Service 

Babysitting Small Business Ideas in Chicago

Why is babysitting on this list?

The working class, executives, and the wealthy population of this metropolis need help with their children at various times of the day and night.

Sometimes, it will be during the day while they work.

Other times there could be late night or overnight sitting needed when they attend events or go out on the town.

You may even find some that need weekend help with their children.

There is a lot of potential in this business and it is ideal for college students

19. Mobile Beauty Salon

Senior citizens, stay-at-home moms, handicapped people, and others who are unable or can seldom leave their homes desire to have their hair and/or nails done.

Taking this business to their doorstep is a step in the right direction for those in need.

This business requires only a small investment if you already have the skills and licensing to work as a cosmetologist or barber.

Haircuts, hairdos, makeup, nails, and other beauty care can be mobile. 

20. Arts & Crafts Business

Arts & Crafts Small Business Ideas in Chicago

If you are good at arts and crafts such as painting on canvas, sketching, crocheting, knitting, or other crafty crafts then you are in the right city.

There are ways to display your arts and crafts all over this city where locals and tourists will see you and buy from you.

Do a little research to find the best locations for this business. 

21. Used Products Seller

Selling used items can be as easy as selling old things you no longer use around your house.

As they say, “One person’s trash is another person’s treasure,” which by no means you should sell your trash.

However, you can sell items you have used and no longer use or items you never used.

You may be adept at repairing things, which is another way to sell used products.

Pick up antiques or vintage items at local thrift stores and sell them online for profit.

There are online and offline ways to start this business.

Do your research and follow the city and state laws.

22. Personalized Custom Products Business 

People like custom and personalized products.

A home-based business where you cater to personal, business, or educational customers can potentially be quite profitable.

Custom items such as mugs, t-shirts, magnets, notebooks, and the like are very popular.

There are places online where you can make designs for free, market them, and make a percentage of the profits.

This business requires a very low investment or no investment other than your time and creativity. 

23. Blogging 

Blogging Small Business Ideas in Chicago

Did you know that blogging has made millionaires out of hundreds of thousands of people?

Some were dead broke with nowhere else to go and others had 9-5 jobs they wanted to quit.

It goes to show you that no matter who you are or where you are from, you can be successful at something.

If you’re already a good writer, you can do it yourself.

If you lack some grammar and spelling skills, you can hire people to do the work for you with a very low investment.

As it is said, “Write what you know,” and you can be a success.

Millionaire bloggers have created recipes, cooking, gardening, home improvement, work at home, career and recruitment, and other kinds of blogs.

Just find your niche and get started.

Remember, that to start making substantial income from blogging, you must be patient, persistent, and consistent.

Write often, post on social media, market yourself, make videos, and give it a few months to a year to show some profit. 

24) Security Agency

Almost everyone is concerned with safety and security nowadays.

Opening a security agency is a brilliant idea in Chicago.

What do you need?

You will need security knowledge and experience, and a team of highly trained people that do the heavy lifting.

Military or martial arts training is a good way to go.

You can go with brawny security guards or you can opt to install security systems for homes and businesses.

Having a well-trained “army” of professional and well-trained security people means you can hire out for events, parties, or residential purposes. 

25) Social Media Manager

Social Media Manager

Social media is at the forefront of marketing and advertising in today’s world.

While print marketing is still a thing and still has its place at the local level, social media expands from local to global levels.

Twitter, Pinterest, Instagram, Facebook, TikTok, Snapchat, and YouTube are a few of the top producers for free and paid advertising and promotions.

If you have some expertise on these social channels you can easily find clients (businesses) that need your help boosting their online presence or managing their social media accounts.

You don’t need a big investment, but you will need to prove your worth and be good at organizing a content calendar for clients. 


These 25 ideas for small business startups could help you find the best business to start in Chicago– they can be used as-is or you can expand and brainstorm to create your own niche. 

Whatever you do, find something you enjoy and turn that into a business through good research and a business plan.

Thinking things through and doing your research are crucial to your success.