Grasshopper vs Sideline (2026): which should you pick?
As of Nov 13, 2026, we pick Grasshopper: it is second in our ranking of business phone systems, and it grades higher too, 3.0 against 1.8.
Checked Oct 17, 2026 and Nov 12, 2026 · graded Oct 17, 2026 and Nov 12, 2026 by ToolGPA
Grasshopper grades higher on value for money, the free plan, features, ease of use and platforms.
Price, platforms and features side by side. The table says where each price was read and when.
Grasshopper
Virtual business number on your own phone, priced per account
Sideline
A second phone number app that runs on your carrier's network
Which one is for you
Pick Grasshopper if
- Fits if you're a solo founder who wants a business line without carrying a second phone
- Works for a few people answering the same number on one bill
Look elsewhere if
- Skip it if you're outside the US and Canada, as that's the only place it's sold
- Not for you if calls need to log into a CRM, since no integrations are on record
- Tight if you need several numbers on Solo Plus, at $9 a month for each extra one
- Watch out: texting needs carrier registration, $19.50 once and $1.50 a month on every plan
- Watch out: only Solo Plus shows a monthly price, $32, and advanced routing needs Small Business at $55
Pick Sideline if
- Fits if you want a second number for selling things or dating without giving out your own
- Works for one person who wants calls to run over the carrier, not wifi
Look elsewhere if
- Not for you if you need a team phone system, since no multi-user plan is shown
- Skip it if you want a stated price from the vendor, as the site shows none
- Pricey if you pay monthly: $14.49 against $129.99 for the year
- Watch out: the App Store lists plans with no billing period, and a Google Play review mentions $9.99
- Watch out: there is no free plan or trial
How we grade them
| 3.0GPAGrasshopperVery good | 1.8GPASidelineWeak | |
|---|---|---|
| Value for money | ASolo Plus is $25 a month billed yearly for unlimited users. Add two $3 extensions so all five of you get one and it's about $6.20 a head, under 60% of this category's cheaper quarter. On your own, True Solo is $14. | B$14.49 a month in the App Store, the bottom of the category's cheapest quarter, and $129.99 a year, about $10.83 a month. Billing periods are not shown on the listing. |
| Free plan and trial | CA 7-day free trial with no credit card needed. No free plan. | FNo free plan and no trial on record, only paid in-app purchases. |
| Features | CA local, toll-free or vanity number, a shared inbox for calls, texts and voicemail, extensions, recording with AI summaries, auto-replies and fax. It does that job fully, but it's a smaller job: no integrations, and advanced routing is on Small Business. | DOne narrow function: a second number with messaging and voicemail. No team or multi-user plan is shown on the pages read. |
| Ease of use | A4.75 from about 46,000 App Store ratings. Pick a number, install the app and the calls start ringing. | BNo store rating on record. It is an app you install and start using, with no ID needed to sign up. |
| Platforms and integrations | BMac, Windows, iPhone and Android apps, so phone and computer are covered. No web app and no integrations on record, which keeps it off the top grade. | CiPhone and Android apps only, plus a web messaging page. Nothing else is connected. |
| Best for | a second business number on your own phone | a second phone number on your own phone |
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: Grasshopper and Sideline. How we grade
Price against what you get
Grasshopper starts at $14 a month and scores 3.0 out of 4 on features, ease of use and platforms. Sideline starts at $14.49 a month and scores 2.0.
Grasshopper scores higher and starts $0.49 a month lower. Of the other business phone systems on the chart, none scores higher than Grasshopper for less, and 8 score higher than Sideline 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
- Grasshopper also covers transcription and shared inbox.
At a glance
| Grasshopper | Sideline | |
|---|---|---|
| Pricing | Free trial | Paid |
| Starts at | $14 per month, billed annually | $14.49 per month as labeled in the App Store (billing period not shown) |
| Free plan | None | None |
| Free trial | 7-day free trial, no credit card required | None listed |
| macOS | ||
| Windows | ||
| iOS | ||
| Android | ||
| Made by | Grasshopper | Pinger, Inc. |
| Price read from | grasshopper.com | apps.apple.com |
| Checked | Oct 17, 2026 | Nov 12, 2026 |
Worth knowing
Grasshopper
- Sold only in the US and Canada; international calls are billed per minute by destination.
- Texting needs carrier registration: a $19.50 one-time fee and $1.50 a month on every plan.
- Extra numbers cost $9 a month each on annual billing ($10 monthly), and extra extensions $3 ($5 monthly).
- The pricing page shows annual prices and says annual billing saves over 20%; only Solo Plus's monthly price ($32) was readable.
Sideline
- Only iOS and Android apps are listed; the site pages read for this entry show no team or multi-user plan.
- The App Store shows several in-app purchases without a billing period, so the plan names are the only guide to monthly or yearly.
- The vendor's own site states no price; amounts come from the App Store listing for the US.
- A user review on Google Play mentions $9.99 a month, which differs from the App Store figures.
Key features
Grasshopper
- A second number on your phone
- Pick a local, toll-free or vanity number and use it through the mobile or desktop app, keeping business calls apart from a personal number.
- Shared inbox
- Calls, texts and voicemails sit in one thread per customer, and the inbox is shared so the whole team sees the same history.
- Extensions and call forwarding
- Forward calls to any number and add extensions for staff or departments: one on True Solo, three on Solo Plus and unlimited on Small Business.
- Recording and AI call summaries
- Call recording with transcription, plus call summaries and AI sentiment drawn from customer calls.
- Automated replies
- Instant Response sends a set text reply when a call is missed, and scheduled auto-replies cover hours when no one is working.
- Virtual fax
- Inbound faxes arrive by email and in the app, without a fax machine.
Sideline
- Second number
- Pick a number in the area code you want, or port in a number you already have, and use it beside your main line.
- Carrier network calls
- Calls use the carrier's cellular network instead of VoIP, so the line works without Wi-Fi, according to the site.
- Unlimited messaging
- SMS, MMS and group messages are unlimited, with an auto-reply that can send a text back after a missed call or message.
- Separate voicemail
- Record a greeting for the Sideline number so callers reach its own voicemail instead of your personal one.
- Spam labeling
- The app suggests names for unknown callers and texters and labels suspected spam, telemarketers and fraud.
- No ID to sign up
- The Google Play listing says an account does not need a government-issued ID and is verified in another way.
Plans
Grasshopper
True Solo$14
per month, billed annually
One user, one local or toll-free number and one extension, with unlimited calls and texts.
Solo Plus$25
per month, billed annually ($32 billed monthly)
Unlimited users at no extra cost, one number and three extensions; more extensions cost $3 a month each.
Small Business$55
per month, billed annually
Unlimited users, four numbers and unlimited extensions, with advanced call routing and call tracking.
Sideline
Monthly plan$14.49
as labeled in the App Store; billing period not shown
In-app purchase listed as Sideline - Monthly plan. The listing also shows Sideline Pro - Monthly at $14.99 and Voicemail to Text at $2.99.
Yearly plan$129.99
as labeled in the App Store; billing period not shown
In-app purchase listed as Sideline - Yearly Plan. The same listing shows older or smaller purchases, from $0.99 to $99.00.
Ways to pay less
Grasshopper
- Annual discount
Annual savings over 20%
Grasshopper's pricing page says annual billing saves over 20%; its comparison page gives Solo Plus as $25 a month annually against $32 monthly.
Sideline
No public discounts listed.
Common questions
Which is cheaper, Grasshopper or Sideline?
As of Nov 12, 2026, Grasshopper is cheaper to start with: $14 a month, against $14.49 a month for Sideline. Grasshopper starts at $14 per month, billed annually, and Sideline starts at $14.49 per month as labeled in the App Store (billing period not shown).
Which has a free plan, Grasshopper or Sideline?
As of Nov 12, 2026, neither Grasshopper nor Sideline has a free plan. Grasshopper has a free trial.
Which platforms do Grasshopper and Sideline run on?
As of Nov 12, 2026, only Grasshopper lists macOS and Windows apps. Both list iOS and Android apps. A platform missing from a listing is one its maker's pages did not mention.
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.