At Windy City Payments, we understand the challenges faced by local businesses.
Proven Track Record
Customer Satisfaction
We Have Completed
Average Answer Time
Trusted by local businesses since 2008,
Windy City Payments understands the challenges local businesses face.
Cost-effectiveness
We provide affordable, transparent point-of-sale solutions designed to lower your operating costs and increase profitability. With competitive processing rates, flexible pricing, and no unnecessary add-ons, Windy City Payments helps local businesses get enterprise-level POS technology without the enterprise-level price tag.
Modern, Restaurant-Ready Technology
We partner with leading POS platforms to deliver fast, reliable, and easy-to-use systems built for today’s businesses. From cloud-based reporting and online ordering to handhelds and contactless payments, our technology keeps you running efficiently while staying ahead of changing customer expectations.
Local Industry Expertise You Can Trust
As a family-owned business based in the Chicagoland area, we understand the needs of local restaurants and retail businesses. We specialize in POS systems for food service and small businesses, offering hands-on setup, menu programming, and ongoing support from people
who actually know your business—not a call center.
Scalable Systems That Grow With You
Whether you’re opening your first location or expanding to multiple stores, our POS solutions scale with your business. Add terminals, locations, online ordering, or advanced features as you grow—without being locked into long-term contracts or outgrowing your system.
POS Solution
We help restaurants, bars, retail stores, service businesses, and mobile merchants upgrade their payments and POS systems without contracts, hidden fees, or wasted time. With fast installation, hands-on training, and free on-site support, we make it easy to switch and start seeing results immediately. Our modern POS and payment solutions are built to streamline operations, reduce costs, and help your business run smarter—not harder. We earn your business every day through transparent pricing, reliable technology, and a partnership mindset focused on long-term growth.
Best-in-Class POS & Payment Technology
We partner with industry-leading platforms like Clover, SkyTab, and Level POS to give you the freedom to choose the technology that fits your business—not the other way around. Whether you’re running a fast-paced restaurant, a growing retail store, or a multi-location operation, we deliver flexible, modern systems built for real-world performance.