Company lists · Data refreshed September 2026

Top 25 AI companies for enterprise software based in Chicago, United States

Name: AI companies for enterprise software based in Chicago, United States
Creator: RevenueBase
License: https://creativecommons.org/licenses/by/4.0/

Compiled by the RevenueBase Data Team Data refreshed Sep 28, 2026 208 companies tracked

RevenueBase identified 208 AI companies for enterprise software headquartered in Chicago, United States as of September 2026 and tracks 19,652 professional contacts across them, including 7,297 with verified work emails. Across the United States, New York is the largest hub for this category (637 companies); Chicago has 208.

This list covers AI companies for enterprise software headquartered in Chicago, United States, matched on what each company actually does as described in its own words. Ranked by team size, largest first. Every row shows the company's own description, its RevenueBase Smart Search rating, and when it was last checked. Data refreshed September 28, 2026.

Published by RevenueBase, a B2B data infrastructure company. This list was built with RevenueBase Smart Search, the natural-language company search RevenueBase customers use to build their own targeted lists and unlock verified emails and direct dials at the companies on them. How these lists are built and judged.

How to read this list HQ checked on every row RevenueBase Smart Search rating on every row Refreshed Sep 28, 2026 86% judged on-target in blind review

208Companies

19,652Contacts tracked

7,297Verified emails

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The 25 largest AI companies for enterprise software based in Chicago, United States

Ranked by team size

Top 25 of 208 AI companies for enterprise software based in Chicago, United States, ranked by team size, largest first. Data refreshed Sep 28, 2026. RevenueBase Smart Search rates how each company's information relates to AI companies for enterprise software: strong evidence (its own description names it), partial (names part of it), indirect (matched on the rest of its profile rather than the description shown). Click a contact count to view that company's people.
#	Company	RevenueBase Smart Search	Headquarters	Employees	Contacts
1	Thoughtworks	Partial evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	10001+	11,634 contacts →
	Partial evidence “We are a global technology consultancy that delivers extraordinary impact by blending design, engineering and AI expertise.” Source: RevenueBase Database · checked Sep 28, 2026
2	Quinnox	Partial evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	1,001-5,000	1,917 contacts →
	Partial evidence “Everforth Quinnox is an AI-first Digital Always organization orchestrating value for forward-looking businesses.” Source: RevenueBase Database · checked Sep 28, 2026
3	Mathco	Strong evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	1,001-5,000	1,831 contacts →
	Strong evidence “TheMathCompany or MathCo® is a global Enterprise AI and Analytics company, trusted for data-driven decision making by some of the largest organizations across industries.” Source: RevenueBase Database · checked Sep 28, 2026
4	66degrees	Partial evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	501-1,000	685 contacts →
	Partial evidence “At 66degrees, we help companies navigate through the complexities of AI, transforming data into intelligent solutions that empower the modern workforce.” Source: RevenueBase Database · checked Sep 28, 2026
5	SPR	Strong evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	201-500	366 contacts →
	Strong evidence “SPR is a tech consultancy that builds AI-powered software designed to set businesses apart.” Source: RevenueBase Database · checked Sep 28, 2026
6	RIVAL	Partial evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	201-500	321 contacts →
	Partial evidence “Rival delivers AI-powered orchestration for HR, helping organizations accelerate time-to-impact across sourcing, candidate engagement, and employee journeys.” Source: RevenueBase Database · checked Sep 28, 2026
7	Ashling	Indirect evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	201-500	229 contacts →
	Indirect evidence “Boutique by design, hyperfocused on intelligent automation.” Source: RevenueBase Database · checked Sep 28, 2026
8	8th Light	Partial evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	51-200	158 contacts →
	Partial evidence “We ship AI.” Source: RevenueBase Database · checked Sep 28, 2026
9	PS Hummingbird	Partial evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	201-500	143 contacts →
	Partial evidence “Hummingbird is an AI-native Microsoft partner.” Source: RevenueBase Database · checked Sep 28, 2026
10	Techavidus	Strong evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	51-200	101 contacts →
	Strong evidence “TechAvidus delivers AI-powered custom software, web, and mobile application development services for startups, SMEs, and large enterprises.” Source: RevenueBase Database · checked Sep 28, 2026
11	Adage Technologies	Strong evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	51-200	91 contacts →
	Strong evidence “Adage is your ideal partner, experienced in software, ecommerce, and AI web solutions that combine strategic thinking with a passion for technology to advance your purpose.” Source: RevenueBase Database · checked Sep 28, 2026
12	Radicle INC	Indirect evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	51-200	91 contacts →
	Indirect evidence Source: RevenueBase Database · checked Sep 28, 2026
13	Business Solutions & Services BSS - USA	Partial evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	51-200	82 contacts →
	Partial evidence “A global AI digital transformation consultancy firm delivering data and AI solutions and services, empowering organisations to modernise their digital journeys.” Source: RevenueBase Database · checked Sep 28, 2026
14	Inrule	Strong evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	51-200	72 contacts →
	Strong evidence “InRule Technology® is an AI decisioning company providing integrated decisioning, machine learning and process automation software to the enterprise.” Source: RevenueBase Database · checked Sep 28, 2026
15	Ultra Consultants	Indirect evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	51-200	60 contacts →
	Indirect evidence “Ultra Consultants is an independent ERP consulting firm guiding manufacturing and distribution companies on their Digital and Business Transformations.” Source: RevenueBase Database · checked Sep 28, 2026
16	Adifice Technologies	Indirect evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	51-200	59 contacts →
	Indirect evidence “Adifice Technologies is an IT development, services and products firm.” Source: RevenueBase Database · checked Sep 28, 2026
17	Logicon, LLC	Indirect evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	51-200	56 contacts →
	Indirect evidence “At Logicon, we help businesses streamline operations, reduce manual work, and make technology effortless.” Source: RevenueBase Database · checked Sep 28, 2026
18	Cloverpop	Indirect evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	11-50	49 contacts →
	Indirect evidence “Top-performing businesses have one thing in common: better decisions.” Source: RevenueBase Database · checked Sep 28, 2026
19	Cepoch	Partial evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	51-200	45 contacts →
	Partial evidence “Cepoch delivers high-quality, reliable solutions in AI, Mobile & Web Apps, Business Intelligence, Salesforce, and Cybersecurity-backed by expert Managed IT Services designed to…” Source: RevenueBase Database · checked Sep 28, 2026
20	Grawlix	Strong evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	51-200	44 contacts →
	Strong evidence “Grawlix is a leading AI-driven software development and performance marketing company based in the USA, empowering businesses to scale faster through intelligent technology and…” Source: RevenueBase Database · checked Sep 28, 2026
21	Quantum Rise	Indirect evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	51-200	41 contacts →
	Indirect evidence “We put the power of artificial intelligence in your hands in ways that create positive change for you, your organization, and the world around you.” Source: RevenueBase Database · checked Sep 28, 2026
22	OLSYS	Strong evidence	Chicago, United StatesHQ checked Sep 28, 2026	51-200	38 contacts →
	Strong evidence “We partner with fast-growth companies, investors, and mid-sized enterprises to scale faster, modernize smarter, and stay ahead in an AI-driven world.” Source: RevenueBase Database · checked Sep 28, 2026
23	Mcsquared AI LLC	Partial evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	11-50	35 contacts →
	Partial evidence “mcSquared.AI specializes in accelerating analytics for businesses seeking the quickest ROI on their cloud and big data investments.” Source: RevenueBase Database · checked Sep 28, 2026
24	Plutus	Indirect evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	11-50	34 contacts →
	Indirect evidence “At Plutus, we help insurance organizations modernize with speed and precision, from strategy through execution.” Source: RevenueBase Database · checked Sep 28, 2026
25	PLEGO	Partial evidence	Chicago, IL, United StatesHQ checked Sep 28, 2026	51-200	33 contacts →
	Partial evidence “Plego is a global web, mobile, Artificial Intelligence, and custom software development agency with offices in Chicago, Houston, Milwaukee, Dubai, Riyadh and Karachi.” Source: RevenueBase Database · checked Sep 28, 2026

RevenueBase Smart Search

RevenueBase Smart Search assesses information from a company’s LinkedIn profile, information supplied directly by the company, its website, and other publicly available sources. It uses that information to rate how closely the company relates to this list’s category: AI companies for enterprise software. Every row carries its rating and the description the rating was read from, so each one can be checked rather than taken on trust.

Strong evidence: The company's own public description of its business names AI companies for enterprise software.
Partial evidence: Its own public description names part of AI companies for enterprise software, so it works in or next to the category without describing itself that way.
Indirect evidence: The description shown does not name AI companies for enterprise software. The match rests on the rest of the company's public profile rather than the one sentence quoted here, so this is the rating to check first.

RevenueBase Smart Search is how these lists are built: RevenueBase's data engine and AI assemble the companies that match a category defined in a user's own words, so a list can be about what companies actually do rather than about whichever industry code they were filed under.

Showing 25 of 208 AI companies for enterprise software based in Chicago, United States

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AI companies for enterprise software based in Chicago, United States at a glance

As of Sep 28, 2026

37.1%Verified-email coverage

94.5Average contacts per company

1-10Median size (employees)

Sep 28, 2026Page data refreshed

Companies by employee count

1-10

121

11-50

51-200

201-500

501-1,000

1,001-5,000

10001+

Email recency for this list is measured across the whole United States list rather than for Chicago, so it is reported there. Company counts and contact totals on this page are exact for Chicago, over 208 companies.

How this list was built

Company categories are rarely black and white. RevenueBase reads each company's own description of its business to decide whether it belongs among AI companies for enterprise software, so some rows will be adjacent to the category rather than pure plays. The description and RevenueBase Smart Search rating on every row are there so you can check each match yourself.

Source: The RevenueBase company graph: 60 million companies and 398.9 million professional contacts resolved from primary sources, queried with RevenueBase Smart Search, the natural-language company search available to every RevenueBase user.
What qualifies: Companies headquartered in Chicago, United States whose own description of what they do matches “AI companies for enterprise software”. Matching reads each company's description, not its industry code or its name.
RevenueBase Smart Search: RevenueBase Smart Search is how this list is assembled and how each row is rated. RevenueBase's data engine and AI assess a company's LinkedIn profile, information supplied directly by the company, its website and other publicly available information, then relate it to a category defined in a user's own words. Each row is rated strong evidence (its own description names AI companies for enterprise software), partial evidence (it names part of the category) or indirect evidence (the description shown names none of it and the match rests on the rest of the company's profile). The description supporting each rating is quoted on the row.
What we exclude: Companies whose own description does not clearly place them among AI companies for enterprise software, and records with no verified work email. Companies headquartered outside Chicago are excluded even when they keep an office there.
Match quality: In blind human judging of this matching method, 86% of matched companies were on target. Expect roughly 1 in 7 rows to be adjacent to the category rather than a pure play. Every row shows the company's own description and its RevenueBase Smart Search rating so you can judge each match yourself. Read the full methodology: how the lists are built, how the judging worked, and what the figure means.
Ranking: Team size, largest first: companies are ordered by the number of professionals RevenueBase tracks at each one. Employee ranges shown are reported bands, for context.
Verification: Every listed company carries at least one verified work email, 7,297 across the full list. Contacts re-verify on a rolling cadence, and each contact's own verification date is shown inside RevenueBase.
Refresh: This page's figures were pulled from the company graph on September 28, 2026. Lists refresh periodically as the graph is re-checked.
Corrections: Wrong category, wrong headquarters, or a company that has closed? Use “Report an issue” on any row. Reports go to the RevenueBase Data Team and feed back into the company graph.

AI companies for enterprise software by metro in the United States

Frequently asked

What is RevenueBase Smart Search?

RevenueBase Smart Search is how RevenueBase decides which companies belong on this list and how strongly each one fits. Its data engine and AI assess a company's LinkedIn profile, information supplied directly by the company, its website and other publicly available information, then relate it to the category the list is about. Each row is rated strong evidence when the company's own description names AI companies for enterprise software, partial evidence when it names part of the category, and indirect evidence when the description shown names none of it and the match rests on the rest of the company's profile.

How many AI companies for enterprise software are there based in Chicago, United States?

RevenueBase identified 208 AI companies for enterprise software headquartered in Chicago, United States as of September 2026, matched on each company's own description of what it does rather than its industry code.

What is the largest company on this list?

Thoughtworks, headquartered in Chicago, tops this list with the largest team on record.

Which city in the United States has the most AI companies for enterprise software?

New York leads the United States with 637 headquartered companies, followed by San Francisco (577) and Austin (384). Chicago has 208.

How do I get contact information for these companies?

A free RevenueBase account lets you run this exact search and work the top results, verified emails and direct dials included. Upgrading unlocks all 7,297 verified decision-maker contacts tracked across these 208 companies.

How current is this list?

The list refreshes periodically as the company graph is re-checked. This page's figures were pulled on September 28, 2026.

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About this data

RevenueBase is a B2B data infrastructure company. Its company graph covers 60 million companies and 398.9 million professional contacts, with emails verified on a rolling cadence rather than scraped once and left to decay. These company lists are generated directly from that graph with RevenueBase Smart Search, the same natural-language company search every RevenueBase user has: describe a market in plain words, get the companies that match, and add verified emails and direct dials for the people at them. It is the same data that powers RevenueBase's B2B data products, and a free account includes 500 credits to start. How these lists are built and judged.