When you need to move from a hobbyist monitor to an enterprise‑grade observability stack, the price gap opens up fast. Checkly’s entry‑level plan lands at $24/month, while Datadog’s cheapest comparable module – the Pro tier – starts at $18/month but quickly balloons as you add logs, APM, and AI credits.
What you actually pay for
Both vendors break out their features into separate line items, so the headline price rarely tells the whole story. Checkly bundles uptime checks, retries, and a modest 1‑minute interval into its Starter tier and upgrades to a 30‑second interval with the Team tier at $64/month. Datadog, on the other hand, sells a la carte components: the Pro plan at $18/month gives you core integrations and 15‑month metric retention, while dedicated log ingestion starts at $0.1/month, standard indexing at $1.7/month, and flexible storage at $0.05/month. Add the AI Credits add‑on at $1.3/month if you want Bits‑powered insights, and you’re already beyond Checkly’s flat fee.
| Vendor | Plan | Price | Included Highlights |
|---|---|---|---|
| Checkly | Starter | $24/month | 1 min interval, retries, startup‑friendly |
| Checkly | Team | $64/month | 30 sec interval, ideal for growing teams |
| Datadog | Pro | $18/month | 1,000+ integrations, 15‑month metric retention |
| Datadog | Enterprise | $27/month | ML‑based alerts, Live Processes, Governance Console |
| Datadog | Ingest | $0.1/month | Out‑of‑the‑box log parsing for 200+ sources |
| Datadog | Standard Indexing | $1.7/month | Log alerts, Watchdog Insights |
| Datadog | Flex Storage | $0.05/month | Up to 15‑month retention without rehydration |
| Datadog | AI Credits | $1.3/month | Bits Chat, Bits Investigation, Bits Code |
If you’re a small team that only needs synthetic checks, Checkly’s Starter tier is a clean, all‑in‑one price. As soon as you need deeper log analytics or APM, Datadog forces you to stitch together multiple line items, and the total quickly eclipses Checkly’s Team price. Conversely, large enterprises that require machine‑learning alerts, live process visibility, and granular governance will find Datadog’s Enterprise tier at $27/month a more appropriate foundation, even if the per‑module add‑ons raise the bill.
Bottom line: pick Checkly if you want a straightforward uptime monitor without the headache of assembling log and trace services. Choose Datadog when you need a full‑stack observability platform and are prepared to pay for each capability separately. Pricing verified on 2026-09-19.