Chicago is my kind of town.

And apparently, a lot of software companies feel the same way. Chicago is home to more than 6,000 tech companies, and nearly 400 startups have been founded in the city over the last five years. 

San Francisco used to be the hot spot for tech. But in recent years, companies have rapidly fled from California to establish headquarters in other major cities, such as New York City, Austin, and – you guessed it – Chicago. 

But while Silicon Valley’s popularity is waning, Chicago’s tech companies are thriving. In 2021, nine Chicago startups achieved “unicorn” status, reaching a valuation of at least $1 billion (humble brag: G2 is one of those unicorns!). 

Chicago might be considered the “Second City”, but it’s well on its way to being number one in tech.

Top 10 software companies in Chicago

Many major companies are located in Chicago, including Boeing, McDonald’s, Kraft Heinz, and United Airlines. With big players like that planting their roots in the Midwest, it’s no surprise that innovative technology companies are flocking to The Windy City. 

And if you’re wondering what exactly makes Chicago attractive to major tech companies, you’re not the only one. A few theories seek to explain this. 

First, the cost of living in Chicago is significantly lower compared to major cities on the east and west coasts. This means lower overhead costs for companies and a relatively more comfortable lifestyle for employees. Second, Illinois is the third-largest producer of computer science degrees in the United States. These graduates then flock to Chicago for software engineering and development jobs.

And third, many people believe that Chicago’s appeal can simply be attributed to the strong work ethic that Midwesterners are known for. But whatever the reason, there’s no doubt that Chicago’s tech industry is on the rise – from fintech and healthcare to e-commerce and information technology (IT).

Top tech companies in Chicago

  • DealRoom
  • Popular Pays
  • Printavo
  • Syndigo
  • Rytr
  • Smokeball
  • Keeper Security
  • FourKites
  • Sprout Social
  • project44

As Frank Sinatra sang, “Chicago is calling me home”. Now it’s time to see which tech companies share Old Blue Eyes’ sentiment. We identified the top software as a service (SaaS) companies in Chicago, based on our own internal data. 

G2 scores products and vendors based on various factors, such as reviews from our user community and data aggregated from online sources and social networks. Learn more about G2’s Research Scoring Methodologies.

*Some user reviews may have been edited for clarity.

10. DealRoom

DealRoom is a due diligence management platform that centralizes transaction data and diligence requests – without unsecured spreadsheet trackers and email threads. The platform’s secure virtual data room and project management tools help companies reduce due diligence time by 25-40%.

“I really like the flexibility of options and configuration that’s afforded by the DealRoom platform. DealRoom can set document-specific permissions and support back-and-forth documented comments. I also appreciated the ability to express relationships between documents; for example, parent-child and/or parallel relationships.”


DealRoom Review, Ammar R.

With DealRoom, companies can perform all due diligence tasks on one secure, comprehensive platform. DealRoom helps streamline communication and offers powerful project data analytics that is not available when standalone rooms are used. DealRoom also features machine learning that mitigates repetitive tasks.

DealRoom at a glance

  • Category: M&A Platforms
  • Website:
  • Founded: 2012
  • Segment: Small business (1-50 employees)

9. Popular Pays

Popular Pays is an influencer marketing platform that connects businesses with content creators. The platform helps brands run campaigns with its comprehensive dashboard that delivers direct communication and powerful analytics.

“I’ve been on Popular Pays since 2013, and I’m constantly impressed. I love the user-friendliness and design of the app, quick responses from the Popular Pays team and brand partners, and the access to amazing campaigns and long-term partnerships I’ve formed. It’s truly one of the best influencer platforms available.”


Popular Pays Review, Nesrin D.

Popular Pays features a network of more than 85,000 creators that make content on any channel. Brands can tap into Popular Pays’s team of strategists to easily kickstart their influencer marketing campaigns and support growth.

Popular Pays at a glance

  • Category: Influencer Marketing Platforms
  • Website:
  • Founded: 2013
  • Segment: Mid-market (51-1,000 employees)
  • G2 Badge: Leader, Winter 2022

8. Printavo

Printavo is used by screen printers, embroiderers, sign manufacturers, and digital printers to manage their online shops. The platform helps brands manage job schedules, artwork approval, quoting, analytics, and payments efficiently.

“Printavo really changed the way our store worked. Before, our team was not sure what to work on next, what was due, and when and where everything was. Now, I can send quotes to customers very quickly and even send them a text message. It has also been useful to collect payments faster by text message.”


Printavo Review, Eric Y.

Printavo helps shops manage their workflows and increase sales by improving communication. Printavo also uses automation to enhance processes. Shops of all sizes rely on Printavo’s robust platform to organize internal processes and effectively grow and scale their businesses. 

7. Syndigo

Syndigo is a product information management (PIM) system that helps brands drive real-time value through a connected commerce ecosystem. The comprehensive platform features omnichannel capabilities to help retailers and distributors make educated decisions and increase sales. 

“This is the first time our organization has a one-stop-shop tool that not only integrates standard webpage content, but also gives us the ability to create enhanced content, manage our data accuracy, and gather insights on how our products are performing on partner websites. The migration from our previous providers to the Syndigo platform was extremely well-supported by various members of the Syndigo team. The training went very well and we are set up for success in the coming months!”


Syndigo Review, Tammi H.

Syndigo continuously optimizes and empowers brands to win at every shelf. Retailers can control all content and data flows and leverage Syndigo’s global two-sided network to harness data growth. Syndigo is truly an end-to-end solution for retailers’ digital assets and product content.

6. Rytr

Rytr is an artificial intelligence (AI) writing assistant that can automatically generate catchy, high-converting content within seconds. Rytr creates original copy for various purposes, including emails, blogs, ads, and social media. 

“Rytr has become a staple with several of my writing projects and tasks. I find myself constantly using it to write blog intros, section headers, emails, video descriptions, and many more. If you are doing writing of any kind, you will definitely enjoy this tool. Rytr even has a Chrome extension so you can use it inside of any text editor, such as SurferSEO and WriterZen.”


Rytr Review, Nathan C.

Rytr features different templates to cover all of your writing needs. The platform’s rich-text editor can help you correct grammar mistakes, check for plagiarism, and polish your ideas. You can also choose from more than 30 languages and over 20 tones of voice, ensuring you express the right emotions and engage with your target audiences.

Rytr at a glance

  • Category: AI Writing Assistants
  • Website:
  • Founded: 2021
  • Segment: Small business (1-50 employees)
  • G2 Badge: Top 50 Office Products, Best Software Awards 2022

5. Smokeball 

Smokeball is a cloud-based legal practice management software that helps increase firms’ profitability and productivity by automatically recording time – whether you bill hourly, with fixed fees, or on contingency. 

“Smokeball has a very intuitive interface with an easy-to-use search tool, which keeps our firm’s information at the tip of our fingers. Smokeball has been an awesome cloud storage file system that is easy to use and customize. The forms are also a huge plus, and finally, the leads have added a new dimension to our practice.”


Smokeball Review, Roberto C. L.

One of Smokeball’s greatest features is its ability to track lawyers’ time. With Microsoft Word and Outlook integrations, Smokeball can automatically track activity to improve efficiency in daily tasks. Smokeball’s mission is to help lawyers achieve less stress and more success.

4. Keeper Security

Keeper Security is a password security and management platform that helps businesses and individuals mitigate data breach risks. The platform generates high-strength passwords, keeps sensitive files in an encrypted digital vault, and securely shares records with teams.

“I have been using Keeper Security’s password manager for more than five months because of my 50+ accounts across many platforms. And the best thing is that it gives me the security I need – specifically, the phone application is far better than any other application I’ve used.”


Keeper Security Review, Gazi Shakibul Islam

Keeper Security is built with a zero-knowledge security architecture; therefore, all encryption and decryption are done locally on the user’s device. With Keeper Security, users can store, share, and manage their passwords, login credentials, bank accounts, and credit card information.

Keeper Security at a glance

  • Category: Password Manager Software
  • Website:
  • Founded: 2011
  • Segment: Mid-market (51-1,000 employees)
  • G2 Badge: Leader, Winter 2022

3. FourKites

FourKites is a supply chain visibility software that combines real-time data and machine learning to help businesses digitize their supply chains. Companies rely on FourKites to help increase productivity, streamline supply chain processes, and increase on-time delivery rates and customer satisfaction.

“Our customer service teams save significant time identifying shipment status by avoiding having to first look in our ERP for shipments numbers, customer purchase orders, part numbers, or sales orders to see the shipment status. Long term, we will send the tracking links directly to our customers so they can track their own shipments and avoid having to contact customer service altogether.”


FourKites Review, Jon K.

With FourKites, businesses can take advantage of multimodal coverage, including truck, rail, ocean, and parcel. FourKites is a real-time visibility platform that identifies trends so you can avoid unnecessary fines associated with detention and late rescheduling. 

2. Sprout Social

Sprout Social is a social management platform that enables brands to take their social media strategy to the next level. With Sprout Social, you can connect with your audience, streamline workflows, collaborate in real time, and uncover meaningful data about your social channels. 

“There’s not a feature I don’t LOVE about Sprout Social! As the social media landscape continues to evolve, Sprout Social is always ahead of the pack when it comes to providing modern marketers with strategic solutions for all facets of social media marketing. This includes everything from sophisticated content scheduling and conversation management tools to robust reporting and social listening features.”


Sprout Social Review, Courtney H.

Social media professionals choose Sprout Social for its easy-to-use platform that is not only intuitive but powerful enough to support large enterprises. Sprout Social features everything needed for social media management, including publishing, engagement, analytics, reviews, social commerce, and social listening tools. 

Sprout Social at a glance

  • Category: Social Media Suites
  • Website:
  • Founded: 2010
  • Segment: Mid-market (51-1,000 employees)
  • G2 Badge: Highest User Adoption, Enterprise, Winter 2022

1. project44

project44 is an advanced visibility platform used by shippers and logistics service providers. The platform offers important shipment information, helps brands automate manual processes, and reshapes the delivery experience for customers. 

“project44 has helped our clients obtain complete visibility of their ocean containers. We love the user interface – it’s super easy to use, customizable, and intuitive. Onboarding new clients is easy, and the tech team has been super helpful with our integration. The tile dashboards have been handy for drilling into port data and quickly prioritizing containers that need action.”


project44 Review, Mike M.

You can use project44 to manage your shipments and track your inventory’s exact location at every step of the journey. You can even collaborate with your supply chain partners via a shared interface to optimize operations. project44 helps shippers and logistics service providers enhance predictability and build trust with their partners and customers.

Sweet home Chicago

Sweet home to major tech companies and startups, that is. Chicago is one of the biggest tech hubs in the country, with a plethora of software startups, incubators, and accelerators. 

There’s no doubt that Chicago’s technology and software development industry is strong. It’s safe to say that entrepreneurs, software solutions companies, and other tech startups will continue to flock to Illinois. 

So one question remains: Who will be the next big technology company to abandon the Pacific Coast for the shores of Lake Michigan?   

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