EVENT SOFTWARE COMPARISON
Check Cherry vs Square Appointments
Square Appointments is great for salons and barbers with recurring clients, simple bookings, and quick payments. Check Cherry is built for events. Here's an honest look at which one fits your business.
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Check Cherry, rated by real event pros
Built to grow with you
Most Check Cherry businesses started as a side hustle. As they grew, added staff, took on more events, and offered more services, Check Cherry grew with them. The platform has been shaped by ten years of feedback from businesses just like yours.
An appointment scheduler can book a time slot and take a payment, but it won't grow into full event management, with contracts, deposits, travel fees, and packages.
Switching systems later is painful, so it's worth getting right the first time. A few dollars a month is small next to your client experience and the hours back in your week. Invest in the system built for where you're headed, not just where you are today.
The differences that actually matter
Both handle online booking and payments. The real question is whether you book appointments or run events. Here's where they differ.
| Check Cherry | Square Appointments | |
|---|---|---|
| Built for | Event pros (DJ, booth, bar, photo, venue) | Appointments for salons & service businesses |
| Booking model | Multi-hour events & packages | Time-slot appointments |
| E-signed contracts | Built in | Not built in |
| Deposits & payment plans | Built in | Pay-at-checkout focused |
| Travel fees & mileage | Built in | Not built in |
| Flex pricing (peak dates, weekday rates) | Built in | Not built in |
| Add-on & equipment inventory | Built in | Not built in |
| Connect Claude or ChatGPT | Built in | Not available |
| Pricing | From $29/mo | Free plan, or from $49/mo |
Based on publicly available information as of July 2026. Square Appointments is an appointment-scheduling product from Square used across service industries; paid plans are priced per location. Both products update often, so check each company's site for current details.
Which one should you choose?
In short: choose Check Cherry if you run multi-hour events that need contracts, deposits, and packages, and choose Square Appointments if you book time-slot appointments and want a free plan.
Choose Check Cherry if
- You run multi-hour events, not time-slot appointments.
- You need e-signed contracts, deposits, travel fees, and packages.
- You run more than one event service, or plan to grow into one.
- You want to ask Claude or ChatGPT about your bookings, leads, and payments in plain English.
Choose Square Appointments if
- You book time-slot appointments for a salon, barber, or similar service business.
- You want a genuinely free plan for a single user.
- You already run your payments through Square and want scheduling in the same place.
A feature list won't tell you the whole story
A lot of event pros run their business across a booking form, a separate contract tool, a spreadsheet for travel fees, a calendar, and a notes app. Check Cherry is the one place where the booking, the contract, the deposit, the travel fee, the staff assignment, and the client's portal all live together and stay in sync.
That's the difference you feel every day, and it's why two tools that both list "contracts" aren't the same thing. When something comes up the week of a big event, you reach a real person who knows event work. It's what customers mention most: everything in one place, and support that actually helps.
So don't stop at the feature table. The best way to compare any two systems is to walk through the customer journey yourself: start a trial, build a package, and book it the way your client would. What your customer experiences is the comparison that matters.
Where Check Cherry is different
The honest differences that matter for an event business
Events, not appointments
Multi-hour event bookings, packages, deposits, and payment plans. Square Appointments is built around time-slot appointments for recurring services.
Contracts built in
E-signed contracts and event paperwork are part of every booking. A general appointment scheduler doesn't include them.
Event pricing built in
Automatic travel fees, peak-date flex pricing, and add-on inventory, tuned to how events are quoted and sold.
Built for the whole event
Run DJ, photo booth, bartending, photography, and event venues from one account, with the planning and staff tools events need.
What event pros say
Real reviews from event businesses on Check Cherry
"Hands down the BEST reservation system on the planet!"
"It's the perfect end-to-end online booking and payment solution. My clients love it!"
"We tried another CRM but setup was a nightmare and tech support took 24 to 48 hours. Check Cherry? Customer service is incredible."
Common questions
Comparing Check Cherry and Square Appointments
Is Check Cherry a good Square Appointments alternative?
For event businesses, yes. Check Cherry is built around multi-hour events with contracts, deposits, travel fees, and packages. Square Appointments is a strong choice if you book time-slot appointments for a salon, barber, or similar service business.
Does Check Cherry do appointments too?
Yes. Check Cherry has an appointments feature for scheduling consultations and meetings, so you get full event management plus simple appointment booking when you need it.
Can I connect Check Cherry to ChatGPT or Claude?
Yes. Check Cherry includes a built-in AI assistant connection (MCP), so you can ask Claude or ChatGPT about your bookings, leads, and payments in plain English. The Check Cherry API and AI assistant connection are included on every plan.
What about my existing Square bookings?
Keep managing existing Square bookings there while using Check Cherry for new events. Many people run both in parallel during the transition, then fully switch once current bookings are complete.
How do I claim the 50% switch discount?
Start your free trial, then chat with our team and show your current Square Appointments plan (a screenshot of your billing page works). We'll apply the 50% discount to your first year.
Switch and Save 50%
Already paying for Square Appointments? Show us your current plan and we'll take 50% off your first year of Check Cherry, and walk you through moving your data over.
Switching is Easy
We'll help you every step of the way
Start Your Free Trial
Sign up and explore Check Cherry free for 14 days. No credit card required.
Show Us Your Plan
Chat with us and show your current Square Appointments subscription to unlock 50% off.
We'll Help You Move Over
We'll walk you through importing your clients, leads, and booking history, so you're not starting from scratch.
See if Check Cherry fits your business
Try it free for 14 days. No credit card required.