Calendly vs When I Work
Two scheduling tools side by side. Prices are the starting plan a small business would pick, in USD.
Short version
When I Work costs less for a six-person team.- When I Work fits retail shop, restaurant or café.
Calendly fits service business, agency or studio.
| Compare | CalendlyCalendly | When I WorkWhen I Work |
|---|---|---|
| In one line | Appointment booking links for client-facing work | Shift scheduling and time clock from $2.50 a user |
| Starting price | From $10/person | From $2.50/person |
| Six-person team | $60/mo | $15/mo |
| Plans | Free for one event type; Standard $10/mo per seat | Essentials $2.50/user/mo; Pro $5/user/mo; Premium $8/user/mo |
| Pricing model | Free tier | Free trial |
| Free trial | — | 14 days |
| Users | Per seat | Per user |
| Both connect to | No shared connections on record. | |
| Also connects to | None in our catalog150+ listed by the vendor | Gusto, Rippling, QuickBooks Payroll, OnPay, Square Payroll |
| Team size | Just me · 2–10 people · 11–50 people | 2–10 people · 11–50 people · 51–200 people |
| Available in | US · UK · CA · AU | US |
| Phone support | Enterprise only | None listed |
| Live chat | Standard and up | Plans not stated |
| Support hours | Email: 24/7 · Live chat: 24/7 · Phone: Monday through Friday, 9am–5pm EST | Web form: Monday-Friday: 7 A.M. to 9 P.M. Central Standard Time, Saturday-Sunday: 9 A.M. to 4:30 P.M. Central Standard Time · Live chat: Monday-Friday: 7 A.M. to 7 P.M. Central Standard Time, Saturday-Sunday: 9 A.M. to 4:30 P.M. Central Standard Time |
| Incidents posted | 0 incidents posted on Calendly's status page in the 90 days to Oct 27, 2026. Status page | 0 incidents posted on When I Work's status page in the 90 days to Oct 27, 2026. Status page |
| Capterra score | 4.7 / 5 from 4,164 reviews | 4.5 / 5 from 1,300 reviews |
| Trustpilot score | 4.1 / 5 from 718 reviews | 4.1 / 5 from 7 reviews (few reviews) |
| Fit: Retail shop | 20 | 85 |
| Fit: Restaurant or café | 10 | 88 |
| Fit: Service business | 92 | 65 |
| Fit: Agency or studio | 88 | 20 |
| Fit: Trades or contractor | 70 | 70 |
| Fit: Online store | 20 | 25 |
| Why people pick it |
|
|
| Where it falls short |
|
|
| Visit Calendly | Visit When I Work | |
Six-person prices are what a team of six would pay on the published plans; "Not listed" means those plans don't cover six. How we calculate prices
More comparisons with Calendly or When I Work
Homebase Scheduling vs CalendlyHomebase Scheduling vs When I WorkCalendly vs JobberCalendly vs ConnecteamCalendly vs Buddy PunchCalendly vs Acuity SchedulingCalendly vs Square AppointmentsCalendly vs SlingCalendly vs SetmoreCalendly vs VagaroCalendly vs SimplyBook.meCalendly vs FreshaCalendly vs BooksyCalendly vs PlandayCalendly vs ModgeJobber vs When I WorkConnecteam vs When I WorkBuddy Punch vs When I WorkAcuity Scheduling vs When I WorkSquare Appointments vs When I WorkWhen I Work vs SlingWhen I Work vs SetmoreWhen I Work vs VagaroWhen I Work vs SimplyBook.meWhen I Work vs FreshaWhen I Work vs BooksyWhen I Work vs PlandayWhen I Work vs Modge