Square, Clover, Toast, SkyTab & SpotOn POS Solutions
Find the Right Point of Sale System with Local Support
Choosing the right POS system can have a major impact on your business operations, employee efficiency, customer experience, and profitability.
At Windy City Payments, we help businesses throughout Chicago and the surrounding suburbs compare, install, train, and support the industry’s leading POS systems including Square, Clover, Toast, SkyTab, and SpotOn.
Unlike national providers, we offer local sales, installation, training, and ongoing support to help ensure your system works the way your business needs it to.
📞 Call or Text (630) 418-6276
Square POS
Best For:
- Small Businesses
- Retail Stores
- Coffee Shops
- Food Trucks
- Quick Service Restaurants
- Startups
Benefits of Square
✔ Free POS Software Options
✔ No Long-Term Contracts
✔ Easy Setup
✔ Integrated Online Ordering
✔ Employee Management
✔ Inventory Tracking
✔ Customer Loyalty Programs
✔ Mobile Payment Acceptance
✔ Online Store Integration
Square is known for simplicity, affordability, and flexibility. It’s often the best choice for businesses looking to get started quickly without significant upfront investment.
Popular Square Hardware
- Square Register
- Square Terminal
- Square Stand
- Square Handheld
- Square Kiosk
Clover POS
Best For:
- Retail Stores
- Service Businesses
- Restaurants
- Professional Services
- Multi-Location Businesses
Benefits of Clover
✔ Highly Customizable
✔ Large App Marketplace
✔ Multiple Hardware Options
✔ Advanced Reporting
✔ Customer Loyalty Tools
✔ Employee Management
✔ Online Ordering Available
✔ Inventory Management
Clover offers flexibility through its extensive app ecosystem, allowing businesses to customize their POS solution to fit unique operational requirements.
Popular Clover Hardware
- Clover Station Duo
- Clover Mini
- Clover Flex
- Clover Kiosk
- Clover Compact
Toast POS
Best For:
- Full Service Restaurants
- Bars
- Pizzerias
- Multi-Unit Restaurant Groups
- Fast Casual Restaurants
Benefits of Toast
✔ Restaurant-Specific Features
✔ Advanced Kitchen Display Systems
✔ Online Ordering
✔ Delivery Management
✔ Table Management
✔ Handheld Ordering Devices
✔ Payroll & Labor Tools
✔ Restaurant Analytics
Toast was built specifically for restaurants and offers extensive restaurant-focused functionality for operations of all sizes.
Popular Toast Hardware
- Toast Flex
- Toast Go Handheld
- Toast Kiosk
- Kitchen Display Systems
SkyTab POS
Best For:
- Independent Restaurants
- Sports Bars
- Family Restaurants
- Pizza Restaurants
- Hospitality Businesses
Benefits of SkyTab
✔ Restaurant Focused
✔ Online Ordering
✔ Customer Loyalty Programs
✔ Delivery Management
✔ Kitchen Display Systems
✔ Mobile Ordering
✔ Real-Time Reporting
✔ Competitive Pricing
SkyTab delivers many enterprise restaurant features while maintaining a simple user experience and attractive pricing structure.
Popular SkyTab Hardware
- SkyTab POS
- SkyTab Mobile
- SkyTab Kitchen Display
- SkyTab Online Ordering
SpotOn POS
Best For:
- Restaurants
- Retail Stores
- Service Businesses
- Hospitality Businesses
Benefits of SpotOn
✔ Cloud-Based Technology
✔ Integrated Marketing Tools
✔ Loyalty Programs
✔ Labor Management
✔ Online Ordering
✔ Reservation Tools
✔ Customer Engagement Features
✔ Multi-Location Reporting
SpotOn combines POS technology with marketing and customer engagement tools to help businesses grow revenue and increase customer retention.
Popular SpotOn Hardware
- SpotOn Register
- SpotOn Handheld
- SpotOn Kiosk
- SpotOn Kitchen Display
Which POS System Is Right For You?
Choose Square If:
- You want simplicity
- You want low startup costs
- You need flexibility
- You are opening a new business
Choose Clover If:
- You want customization
- You need industry-specific apps
- You want multiple hardware options
Choose Toast If:
- You operate a full-service restaurant
- You need advanced restaurant features
- You manage multiple restaurant locations
Choose SkyTab If:
- You want restaurant functionality without enterprise pricing
- You need online ordering and delivery tools
Choose SpotOn If:
- Marketing and customer retention are priorities
- You want an all-in-one growth platform
Why Businesses Choose Windy City Payments
Unlike buying directly from a national provider, Windy City Payments offers:
✅ Local Chicagoland Support
✅ On-Site Installation
✅ Staff Training
✅ Data Conversion Assistance
✅ Menu Programming
✅ Ongoing Customer Support
✅ Multiple POS Options
✅ Competitive Processing Programs
We Help You Compare Before You Buy
Our goal is simple: recommend the POS system that best fits your business—not the one with the biggest marketing budget.
Whether you’re opening a new business, replacing an outdated POS system, or looking to reduce payment processing costs, our team can help.
Schedule Your Free POS Consultation
Discover the best POS solution for your business with expert local guidance, installation, training, and ongoing support.
🌐 WindyCityPayments.com
Local POS Experts Serving Chicago, Naperville, Aurora, Joliet, Schaumburg, Oak Brook, Downers Grove, Lisle, Bolingbrook, Elmhurst, Wheaton, and the Entire Chicagoland Area.


