Custom software, web application, & mobile app development.
"The experts you wish you called, the first time."

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Pleasant Solutions is a renowned, award-winning custom software development firm with high-profile clients across the globe. We provide local software application development in Chicago. Over half of our business comes from clients who have had poor experiences with other software developers in the past and want us to redo their project or take over development. That is why our official motto is: “Experts you wish you called, the first time.”

Headquartered in Canada with office locations throughout North America, we hire only the most highly-skilled talent. With your project in the hands of Pleasant Solutions, you can expect worldclass quality that is never outsourced overseas.

Unlike with smaller firms or start-ups, our clients benefit from our ability to leverage hundreds of building blocks to drive some tasks down from hundreds of hours to just a few, saving time and money. Our projects benefit from the expertise and collaboration of our many departments, including our tenured Project Managers, Business Analysts, Programmers, and Designers. Our high-security standards far exceed that of typical software development companies – our software manages highly confidential information for numerous governments, airports, hospitals, and IT companies. Our clients have peace of mind knowing rigorous security comes standard with all our projects.

We look forward to providing you with a free consultation and showing you why we’re the premier software development company in Chicago.




Canada's 500 Fastest Growing Companies, Profit Magazine
Security Audited
Fast Growth 50 Award, Venture Magazine


  • Environment Canada
  • Bell Mobility
  • Telus
  • PCL Consturction Company
  • Molson Coors
  • MLS Listings
  • U.S. Department of Energy
  • Xerox
  • Alberta Health Services







Custom Software Development

Custom built software can evolve your operations to a level that out-of-the-box solutions simply cannot.
Custom Application Development
(Web & Mobile Apps)

Productivity and profitability increase when your team is able to use their software applications from anywhere, on virtually any device.
Custom Integrations

Custom integrations to enable the transfer of data and workflows seamlessly between different servers, systems, and software.
Design Services

You can have it all: our work looks great and works great! Some of the services we provide include: User Experience (UX) & User Interface (UI) Design, Graphic Design, Logo Design, Motion Graphics, and Video Production.








Pleasant CLM for IT Service Providers    Enterprise Software & SaaS

Pleasant CLM for Infrastructure & Cloud Service Providers    Telecom & Data Centers

Pleasant CLM for Suppliers of APIs & SaaS (Software)    Outsourcing & IT Services

Pleasant CLM for Executive Recruiter Firms    Government, HR, & Legal

Pleasant CLM for Loan & Credit Providers    Banks, Stock Market, & Financial

Pleasant CLM for 3rd Party Logistics Firms    Transport, Logistics, & eCommerce

Pleasant CLM for Energy & Industrial Utilities Suppliers    Oil, Energy, & Utilities

Pleasant CLM for Medical Devices Companies    Medical Devices & Healthcare

Pleasant CLM for Chemical Suppliers    Pharma & Life Sciences

Pleasant CLM for Publishing Houses    Education & Publishing

Pleasant CLM for Suppliers of Electronic Goods    Electronics & Manufacturing

Pleasant CLM for Suppliers of Electronic Goods    And many more







Software Development Chicago

Pleasant Solutions provides many world-class services including custom software design, web application development, and mobile application development in Chicago.

Our office is located in the Aon Center (Chicago’s fourth-tallest skyscraper) near the eastern edge of the Chicago Loop. The nearby ‘L’ Train connects directly to O’Hare International Airport, making us easily accessible to out-of-town visitors. The office is mere steps away from Millennium Park, site of the iconic Cloud Gate sculpture (aka ‘the Bean’), and the Art Institute of Chicago, one of America’s largest and oldest art museums. In the early 2020s, the building will open a brandnew observation deck on its 83rd floor—the Aon Center Observatory— featuring America’s largest and fastest exterior glass elevator and a heart-stopping thrill ride called the ‘Sky Summit.’

Chicago’s metropolitan area (‘Chicagoland’), on the shores of Lake Michigan, is home to nearly 10 million people, making it the third most populous urban area in the U.S. Its highly diversified local economy boasts many Fortune 500 companies—including Walgreens, Boeing, Archer Daniels Midland, United, Allstate, Kraft Heinz, McDonald’s, and others. O’Hare International Airport, with direct flights to well over 200 destinations, is one of the world’s busiest transportation hubs.

Chicago is also a major tourist destination—in the U.S.A., only New York City attracts more visitors. Its downtown skyline features dozens of glorious historic skyscrapers, and some of the world’s tallest modern towers. The city is home to several legendary theater companies including the Goodman Theatre, the Steppenwolf Theater Company, and legendary improv comedy mecca The Second City. Chicago is also famous for its shopping, restaurants, museums, and professional sports teams—the Bears (NFL), the Bulls (NBA), the Cubs and White Sox (MLB), and the Blackhawks (NHL).

While there are other software companies in Chicago, there’s a reason our clients refer to us as “the experts you wish you called, the first time.” We look forward to providing you with a free consultation and showing you why we’re the most responsive and reliable software development company in Chicago.