Selecting Chicago as the location for your entrepreneurial investments will provide a population of nearly three million people as potential customers. A viable business idea bolstered by Chicago billboards and additional forms of advertising has the potential to be quite lucrative. What follows is a list of ten small businesses that could easily flourish in a large city such as Chicago.

Short Term Rentals

Chicago sees numerous visitors for business, education, and leisure. Affordable and comfortable places to stay can be in short supply during high traffic periods of the year. Renting out part of your own home or purchasing a property for rental use through affiliates such as Airbnb or VRBO can be a substantial source of income. Adding perks such as free city tours and meals or snacks will get your rental noticed and garner positive reviews to attract new clients.

Bike Repair and Supply

The Bike 2015 Plan set in place infrastructure and promotion of bike usage throughout the city of Chicago. With 200 miles of protected on-street bike lanes, off-road bike trails, and plentiful areas to park and lock up bicycles many clients exist for sales and repair. The city also offers rental bikes that may need servicing or replacement. With Chicago’s push to make biking safer and more accessible, this industry could see continued growth.


A business that specializes in delivering goods and services, or transports a client to a destination is always a need in a city as large as Chicago. This can start with a single vehicle and quickly grow as demand increases. Food delivery, dry cleaning pick-up, or larger shipping and moving of goods are all potential markets to explore.

New and Vintage Clothing

A large population needs a variety of clothing shopping options. Boutique style clothing, consignment for children and adults, high fashion, and curated vintage styles all have a place in a vibrant city. Focusing on athletic clothing for those utilizing the biking-friendly atmosphere of Chicago is also a potential business model.

Food Trucks

Busy cities need quality food on the go, and the best example of that are the food trucks that dot areas of big business and entertainment. The plus of running a restaurant out of a truck is the ability to quickly and easily move your shop front to wherever the demand is. Pair this with an active social media account and your fans will never miss where you land for the day. 

Bars and Gathering Spots

Large cities need places to maximize relaxation while away from work. A cocktail room, barcade, and a retro tea house are all fixtures in the Chicago social scene. Proper brainstorming and financial wizardry could produce a trendy-themed locale some loyal patrons could call a home away from home.

Cleaning Services

Whether it is just general janitorial cleaning or specialized demo and renovation of a damaged space, an affordable cleaning service is a useful addition to any thriving city. Startup costs can be small but the profits can be substantial. Specialization in rehabbing a location after various disasters is a potential market to explore as well.

Event Hosting Services and Venue

A versatile space that can host a wedding or musical event is a valuable investment. Add to this a team that has expertise in event planning and hosting and you could have a lucrative startup. This may have a lot to do with networking, social media, and target advertising to build clientele. If you tend towards extroversion, this could be the business you are looking for.

Architectural Salvage

As cities grow and their original structures age it is common to see a building with interesting features become next in line for demolition to make room for modern construction. A city with Chicago’s history has a lot of architectural details that deserve preservation. A warehouse set up to take in curated salvaged pieces and make them available for sale could be just the business for someone with a deep appreciation of architectural stories inherent in America’s large cities.

Social Media Marketing

With specialized training and minimal equipment, you could be assisting other businesses’ growth and reach new audiences with social media advertising. The right team of industry-savvy pros at your side will get your potential clients interested and fill your portfolio with satisfied and flourishing local businesses.

These are only a few of the options a city the size of Chicago has to offer. If you are serious about making this the home of your startup, a visit to the local small business administration could help you focus on the current needs in the area and how best you can help fulfill them.