Top Managed IT Companies in Chicago

ThePickle.com

Memorable Name. Serious IT.

✓ Verified Provider Est. 2007
Chicago, IL
1–9 employees
Founded 2007
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ThePickle.com is a managed IT services provider based in Chicago, IL, operating since 2007. It focuses on Managed IT Services, Cybersecurity, IT Help Desk & End-User Support, Microsoft 365. Compare it against other Chicago managed IT providers, then request a quote.

Vetted by the Best IT MSP editorial team · Last updated June 2026

About ThePickle.com

ThePickle.com provides managed IT, cybersecurity and Microsoft 365 support to growing businesses (roughly 10-100 employees), emphasizing structured, proactively managed and security-first environments over reactive break/fix support.

Services Offered

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Managed IT Services
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Cybersecurity
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IT Help Desk & End-User Support
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Microsoft 365

Why Choose ThePickle.com

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Based in Chicago

ThePickle.com is headquartered in Chicago, IL, so Chicago businesses get a local team for on-site work instead of a distant call center.

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Targets 10-100 employee companies centered on

Targets 10-100 employee companies centered on Microsoft 365 with no/thin internal IT

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Positions against reactive competitors with

Positions against reactive competitors with structured, security-first, accountable operating model

Location

Chicago, IL

Certifications & Compliance

Targets 10-100 employee companies centered on Microsoft 365 with no/thin internal IT
Positions against reactive competitors with structured, security-first, accountable operating model

Frequently Asked Questions

Which IT services does ThePickle.com provide?

ThePickle.com delivers Managed IT Services, Cybersecurity, IT Help Desk & End-User Support, Microsoft 365 to organizations across Chicago, IL.

What area does ThePickle.com serve?

ThePickle.com is based in Chicago, IL and supports businesses across Chicago and the greater metro area.

When did ThePickle.com start?

ThePickle.com has been operating since 2007.

Is ThePickle.com certified?

ThePickle.com carries Targets 10-100 employee companies centered on Microsoft 365 with no/thin internal IT, Positions against reactive competitors with structured, security-first, accountable operating model.