As the third-largest city in the country, it’s no surprise Chicago is home to some of the world’s largest companies. McDonald’s, Boeing and Mondelez all call Chicago home.

While the city is known for being at the forefront of the food and beverage, manufacturing and finance industries, its status as a tech hotspot flies under the radar. Dozens of the country’s top software, fintech and SaaS startups came out of the Windy City, and many more are still operating there today.

Here are 25 of our favorite software companies in and around Chicago.


ActiveCampaign is a comprehensive email marketing, CRM and marketing automation platform used by over 150,000 B2B and B2C businesses in 170 countries. Through its services, you can manage your entire customer experience workflow with one platform and deepen relationships at every touchpoint.


Basis (formerly Centro) is a leading provider of marketing automation and intelligence solutions. From planning and ops to reporting and reconciliation, marketers can manage everything in one platform. This leads to an average 35 percent increase in productivity and a 48 percent return on investment.


BigTime is a Chicago-based, private equity-funded SaaS company that helps over 2,000 professional service firms with time tracking and billing. In total, they track over $4 billion of billable time each year. No wonder, then, that they’ve been named the number one professional services automation software by G2.


CellTrak develops GPS-powered SaaS tools for the home healthcare and hospice industries to automate the professionals’ workflows and reduce labor costs. It does this through cloud-based point of care, electronic visit verification and field force management solutions.

Club Automation

Club Automation is a leading software provider for member-based health and athletics clubs. It provides a complete web-based solution to help owners and operators manage the front and back end of their business. That includes marketing, payment, member engagement and more.

Skyscraper on Michigan Ave in Chicago; Software Companies in Chicago concept


Since 1998, Envoy has been using its software to streamline the visa application process for employers and employees. While the process remains a real pain point for millions of applicants, Envoy combines top legal talent with its proprietary platform to increase efficiency and transparency for its clients. As a result, companies can hire and manage the very best talent, regardless of where they live.

SAP Fieldglass

SAP Fieldglass is a cloud platform for the modern external workforce. Founded in 1999 to help companies improve how they find and manage external talent, the company now has over 1000 employees speaking 21 languages across more than 180 countries.


Want to improve the way you find, recruit and integrate new talent? Try Hireology. The cloud-based solution currently helps 6,500 companies attract and hire the best people by combining all recruitment steps into one platform. G2 has recently praised the platform’s customer support and labeled it a “high performer.”

InContext Solutions

InContext’s principal product, ShopperMX, models 3D simulations of retail environments to prototype and optimize designs. The results are impressive. Clients see savings of 90 percent, get results ten times faster and obtain three times more data than in-store testing. The company’s client list is a who’s who of companies producing consumer goods: Samsung, Kellogg’s, Nestle and Coca-Cola, among others.


Inteliquent is the largest independent cloud communications platform in the U.S. with the highest quality network. It powers more than 110 million phone numbers and has more than 300 billion minutes of use annually. It’s trusted by leading companies like Zoom, Twilio and Ooma.


JellyVision and its platform, ALEX, help employees to make wise choices and take control of their healthcare spending. The platform is used by 20 percent of Fortune 500 companies and over 18 million employees in total. It has influenced over $169 billion in premiums since 2015 and helped consumers save $79 million in payroll taxes last year.


Logiwa is a leading cloud fulfillment software for direct-to-consumer brands, wholesalers and third-party logistics providers. Built by a team with decades of experience building, managing and scaling their own warehouses and fulfillment centers, it offers everything a business needs to streamline and scale its operations.


The team at MILYLI is dedicated to making eDiscovery easier with a suite of products and plug-ins. Blackout is an automated redaction tool and the easiest way to redact information in Relativity; Chronicle helps teams build defensible privilege logs; Delegate empowers users to manage groups and workspaces.


OneSpan creates a range of digital solutions to protect users from fraud. That includes digital identity verification, e-signature tools, mobile app shielding and fraud analysis designed to protect every step of the customer journey. Over one-half of the top 100 global banks rely on OneSpan solutions to protect their most important relationships and business processes.


OppLoans is a fintech platform that helps credit-challenged consumers with their financial situation. Over 550,000 customers use OppLoans to improve credit access, enable savings and build wealth.

Origami Risk

Origami Risk is a SaaS solutions provider for the insurance industry. Its suite of risk and workflow management solutions is completely customizable and managed from a single platform. Founded in 2009, the company now has more than 300 employees and supports over 600 companies across the insurance ecosystem.

Chicago from space at night, Software Companies in Chicago concept


Paylocity, headquartered in Schaumburg, IL, offers a payroll and HR solution for the modern workforce. Its cloud-based all-in-one solution is used by businesses big and small, from local stores to global corporations. The company prides itself on its culture. Little surprise, then, that it’s been called one of the best-led companies by INC and Steve Beauchamp named a Glassdoor top CEO.


PerkSpot’s proprietary platform helps companies deliver personalized perks like discounts, savings and rewards to their employees. The company works with more than 10,000 businesses around the world, including Lyft, Verizon, and GrubHub, to build more thoughtful rewards programs and better places to work.


Pricefx is a SaaS pricing solution that empowers companies to maximize margins, increase profits and close better deals. It’s a global company headquartered in Germany, with American offices in Chicago. To that end, it boasts some of the biggest companies in the world as clients, including Bosch, Danone, Mercedes-Benz, and Michelin.


Showpad is a sales enablement platform for the modern sales professional. Founded in Belgium, it opened its Chicago headquarters in 2017. The solution, used by brands like General Electric and Xerox, combines industry-leading coaching and training with content solutions in one platform. As a result, customers see an average increase of 10 percent in sales productivity, a 25 percent increase in marketing productivity and a reduction in onboarding times of 25 percent.

Silkroad Technology

Silkroad Technology offers a complete HR solution to businesses of all sizes. From recruitment to onboarding to employee engagement, the company offers everything you need to help your employees and business to thrive.

Spark Hire

Spark Hire makes holding video interviews a breeze. Over 6,000 companies, including Ikea, Volkswagen and USPS, use the platform to improve the quality of the interviewing process. With Spark Hire, you can hold pre-recorded interviews, interview candidates remotely, and share interviews across your organization.

Sprout Social

Sprout Social is a social media management platform used by more than 25,000 brands and agencies worldwide. It is regularly rated a leading product by G2, Capterra and Top Rated, and is trusted by brands including Columbia, Subaru and Shopify. With Sprout Social, you can increase engagement levels, schedule posts, listen to customer conversations and analyze everything, thanks to some of the richest social data in the industry.


Tock is an all-in-one platform for the hospitality industry. With Tock, you can manage reservations, pickup, delivery, events and waitlists in one place. Hospitality companies can also stay connected with customers with automated two-way messaging and get access to all of the marketing tools you need. Tock has been named one of Fast Company’s most innovative companies of 2021.


TRYTN is a SaaS booking system for tour and activity companies. Through features like a booking engine, reservation management, staff management and automated communication, the software streamlines operations and helps tour companies save time and money. And with partners in over a dozen countries, what started in Chicago is now available across the world.

images by: Jonathan / Flickr, NASA / Flickr, Trey Ratcliff / Flickr

Casey Meehan