InvoiceFly vs Square Invoices (2026): which should you pick?
As of Nov 13, 2026, Square Invoices grades higher than InvoiceFly: 2.8 against 2.2 out of 4.0.
Checked Oct 17, 2026 and Nov 13, 2026 · graded Oct 17, 2026 and Nov 13, 2026 by ToolGPA
InvoiceFly grades higher on value for money. Square Invoices grades higher on the free plan and ease of use. They get the same grade on features and platforms.
Price, platforms and features side by side. The table says where each price was read and when.
InvoiceFly
Invoice and estimate app for contractors and small businesses
Square Invoices
Free invoicing, estimates and contracts inside Square's payment plans
Which one is for you
Pick InvoiceFly if
- Fits if you are a contractor who sends invoices from a phone
- Works for one small business that wants a yearly price under $100
Look elsewhere if
- Not for you if you want a free plan, as there is none
- Tight if you do not want to enter a card, as the trial needs one
- Pricey if you pay weekly, at $8.99 a week against $98.99 a year
- Watch out: each business needs its own account and subscription
- Watch out: Stripe and PayPal charge their own card fees on top
Pick Square Invoices if
- Fits if you already take payments in person with Square
- Works for service businesses that want no monthly fee and can live with 3.3% + 30¢ per online card payment
Look elsewhere if
- Too light for keeping the books, as it only sends payments on to QuickBooks Online or Xero
- Pricey if you go for Plus just for lower fees: $49 a month per location pays off only past about $12,000 a month in card payments
- Not for you if you bill clients in other currencies, since it takes one currency only
- Watch out: every payment has a fee, 3.3% + 30¢ on an online card and 1% on a bank transfer, $1 minimum
- Pricey if you need payroll, a separate product from $35 a month plus $6 per person paid
How we grade them
| 2.2GPAInvoiceFlyFair | 2.8GPASquare InvoicesGood | |
|---|---|---|
| Value for money | B$98.99 a year is about $8.25 a month, inside the cheaper quarter of accounting tools. The weekly plan at $8.99 a week is about $39 a month. | DPlus is $49 a location a month, where the dearest tenth of accounting tools starts. For invoicing it mostly buys a lower card fee, 2.9% instead of 3.3%, plus batch invoices and payment schedules. That fee cut only pays for itself past about $12,000 a month in card payments. |
| Free plan and trial | DA free trial that needs a card and whose length is not stated, and no free plan. | AUnlimited invoices, recurring invoices, deposits, reminders, estimates and contracts cost nothing a month, with no cap. You pay per payment instead: 3.3% + 30¢ on an online card, and 1% on a bank transfer. |
| Features | CInvoices, estimates, payments, expenses and receipt scanning do the invoicing job, but one account covers one business only. | CInvoices on any schedule, deposits, auto-pay, estimates, e-signed contracts, a project workspace and cards, Cash App Pay, ACH or Afterpay. It does invoicing fully, but that's the smaller job: it keeps no books and takes one currency only. |
| Ease of use | CA phone and web app where you set up your business, templates and payments, and no store rating on record. | A4.8 from 93,229 App Store ratings, the top band in this category. If you already take payments with Square, invoices sit in the same account. |
| Platforms and integrations | BWeb, iOS and Android, with payments through Stripe and PayPal only. | BWeb, iPhone and Android, with QuickBooks Online, Xero, Afterpay, Cash App Pay, Apple Pay and Google Pay. There's no desktop app, which keeps it off an A. |
| Best for | invoices and estimates for contractors | free invoicing for businesses already on Square |
The GPA is the average of the five grades: an A is 4 points, an F is none. The full reasons are on each tool's page: InvoiceFly and Square Invoices. How we grade
Price against what you get
InvoiceFly starts at $8.25 a month when paid by the year and scores 2.3 out of 4 on features, ease of use and platforms. Square Invoices starts at $49 a month and scores 3.0.
Square Invoices scores higher, and starts $40.75 a month higher: the question is whether the extra is worth that to you. Of the other accounting and invoicing tools on the chart, 11 score higher than InvoiceFly for less, and 3 score higher than Square Invoices for less.
Features, ease of use and platforms, averaged
What paid plans start at, a month (each step along is roughly double) →
- The best score at each price
- Has a free plan
- No free plan
Where they differ
- InvoiceFly also covers expense tracking and quotes and estimates.
At a glance
| InvoiceFly | Square Invoices | |
|---|---|---|
| Pricing | Free trial | Free plan |
| Starts at | $98.99 per year, or $8.99 per week billed weekly | $49 per location / month, billed monthly |
| Free plan | None | Square Free: unlimited invoices, recurring invoices, deposits, reminders, estimates, contracts and projects. Online card payments cost 3.3% + 30¢. |
| Free trial | Free trial; a card is required and its length is not stated | 30-day free trial of Square Plus or Square Premium |
| Web | ||
| iOS | ||
| Android | ||
| Made by | Labhouse Mobile SL | Block, Inc. |
| Price read from | invoicefly.com | squareup.com |
| Checked | Nov 13, 2026 | Oct 17, 2026 |
Worth knowing
InvoiceFly
- There is no free plan; the trial needs a payment card and converts to a subscription.
- Each business needs its own account and subscription; multiple businesses on one account is not supported yet.
- Stripe and PayPal charge their own card-processing fees on top of the subscription.
- The weekly plan costs $8.99 a week, so it is the more expensive way to pay over a year.
Square Invoices
- Invoices come with Square's general plans, which also cover point of sale and bookings; Plus and Premium are charged per location.
- Each payment has a fee: invoice card payments are 3.3% + 30¢ on Free and 2.9% + 30¢ on Plus or Premium, ACH 1% ($1 minimum).
- It does not keep books: Square sends payments to QuickBooks Online or Xero, and it accepts one currency only.
- Square Payroll is a separate product, from $35 a month plus $6 per person paid.
Key features
InvoiceFly
- Invoices and estimates
- Unlimited invoices and estimates on both plans, with recurring invoices and invoice signatures listed on the site.
- Online payments
- Clients can pay by card or online through Stripe and PayPal, which charge their own fees.
- Expense tracker and reports
- Expenses are tracked in the app, with business reports and a dashboard of invoices and clients.
- Payment notifications
- The mobile app sends notifications when invoices are viewed or paid.
- Time tracking and receipt scanning
- The product menu lists time tracking and a receipt scanner app alongside invoicing.
- Free templates and generators
- The site offers free invoice templates and an invoice generator that can be used before signing up.
Square Invoices
- Invoices and recurring billing
- Send unlimited invoices by email, text or link, on daily to yearly schedules, with deposits, automatic reminders and auto-pay from a saved card.
- Ways to pay
- Customers pay by card, Apple Pay, Google Pay, Cash App Pay, ACH bank transfer or Afterpay, online or in person.
- Estimates and contracts
- Send estimates and e-signature contracts built from reusable templates. Plus adds multi-package estimates and automatic conversion to invoices.
- Project workspace
- Keep each job's invoices, estimates, contracts and notes in one place and track what is paid, unpaid or overdue.
- Payment schedules and batch invoices
- Square Plus splits one invoice into milestone payments and sends one invoice to many customers at once.
- Fast access to funds
- Transfers to your bank arrive the next business day for free, or instantly for a fee, or land at once in a Square Checking account.
Plans
InvoiceFly
Weekly Plan$8.99
per week, billed weekly
Full access: unlimited invoices and estimates, card and online payments, expense tracker and reports, mobile app and notifications.
Yearly Plan$98.99
per year, billed annually
The same features as the weekly plan; the site shows it as $1.90 a week and a 78% saving against paying weekly.
Square Invoices
Square Free$0
Unlimited and recurring invoices, deposits, reminders, estimates, contracts with e-signature and a project workspace. You pay only processing fees.
Square Plus$49
per location / month, billed monthly
Adds batch invoices, milestone payment schedules, custom templates and fields, multi-package estimates, lower online card fees and a $10 ACH fee cap.
Square Premium$149
per location / month, billed monthly
Everything in Plus, with the lowest in-person card fees and 24/7 phone support.
Square ProCustom
For businesses processing over $250,000 a year: custom pricing and processing fees, onboarding help and account management.
Ways to pay less
InvoiceFly
- Annual discount
78% saving on the Yearly Plan
The pricing page shows the yearly plan at $98.99, about $1.90 a week, which it labels as a 78% saving against weekly billing.
Square Invoices
No public discounts listed.
Common questions
Which is cheaper, InvoiceFly or Square Invoices?
As of Nov 13, 2026, InvoiceFly is cheaper to start with: $8.25 a month when paid by the year, against $49 a month for Square Invoices. InvoiceFly starts at $98.99 per year, or $8.99 per week billed weekly, and Square Invoices starts at $49 per location / month, billed monthly.
Which has a free plan, InvoiceFly or Square Invoices?
As of Nov 13, 2026, only Square Invoices has a free plan. InvoiceFly does not, though it has a free trial.
More comparisons
How this page was made
- The verdict at the top follows a fixed rule. When both tools are in the same category and either is in our top three for it, the verdict follows that ranking: the higher-placed tool is our pick. The top three weigh who each tool suits as well as its grades, so a pick can go against the GPA. Otherwise the page does not pick one and says which grades higher: the higher GPA first; on a tie, the one with a free plan, then the one that starts cheaper in dollars a month, counted the same way for both; if they are still level, what the choice depends on.
- The grades are our own, from each tool’s review or report card. The GPA is their average.
- Prices, plans and platforms come from each tool’s listing. The table above says where each price was read and when.
- The differences and the answers to the questions are worked out from those listings.