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Top Cannabis Companies in Chicago, IL (30)

Inspira Financial
3 Offices
1,934 Employees
52 Benefits Hiring Now
Inspira Financial's innovative financial wellness solutions help people plan, save, and invest.

Inspira Financial provides health, wealth, retirement, and benefits solutions that strengthen and simplify the health and wealth journey. With more than 7 million clients, representing over $62 billion in assets, Inspira works with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners — helping the people they care about plan, save, and invest for a brighter future. Inspira...

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Inspira Financial

Inspira Financial's Top Stability & Growth Strengths

Strategic Partnerships: Partnerships with Ameritas and CAIS extend distribution into retirement platforms and advisor channels, opening access to additional customers. These integrations are positioned to expand reach for health savings accounts and alternative-investment custody and administration.

Product Line Growth: Acquisitions and launches such as First Dollar, an AI-enabled benefits platform, and the Riser Benefits rollout expand capabilities across health, retirement, and benefits. This points to continued product investment and a broader service portfolio.

Strong Market Position & Advantage: Scale with more than 8 million clients, over $62 billion in assets under custody, and relationships with many of the largest retirement-plan recordkeepers indicate substantial positioning. Recognition on Crain’s Fast 50 and targeted acquisitions further reinforce competitive standing.

Sunnyside
Cannabis • Retail
5 Offices

Sunnyside is a dispensary focused on cannabis and wellness, offering medical and adult-use marijuana products. They operate dispensaries in multiple states and provide online shopping for various cannabis products.

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Sunnyside
aerīz
Cannabis
2 Offices
59 Employees

aerīz is a national aeroponic cannabis cultivator. We provide patients with pure & consistent aeroponically cultivated cannabis. We're fast growing, with cultivation centers in Illinois and Arizona...plus more on the way. Apply today to join our organization!

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aerīz
Terrabis
Cannabis • Retail
6 Offices
88 Employees
Hiring Now

Terrabis is a privately held, multi-state cannabis operator headquartered in Missouri, with four Missouri dispensaries, a product manufacturing facility in Kansas City, and four dispensaries in Illinois. Terrabis prides itself on being a trusted partner in the cannabis community, offering only the highest quality products and information. We are a team of dedicated cannabis professionals creating the best possible experience for...

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Terrabis
Green Thumb
Cannabis • Retail • Pharmaceutical
Chicago
4,700 Employees
28 Benefits
We are growing green for good and championing everyone's journey to well-being.

We are a national cannabis consumer packaged goods company and retailer. Our mission is to promote well-being through the power of cannabis while giving back to the communities in which we serve. Established in 2014, Green Thumb employs over 4,800 people and serves thousands of patients and customers each year. Green Thumb manufactures and distributes a portfolio of branded cannabis products...

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Green Thumb

Green Thumb's Top Stability & Growth Strengths

Profitability: GAAP net income was positive in 2025 and Q1 2026, with normalized EBITDA margins around 31%, indicating consistent earnings power relative to peers. Margins remained solid even as the company expanded stores and navigated a competitive environment.

Healthy Cash Flow: Operating cash flow reached roughly $295 million in 2025 and $76 million in Q1 2026, supporting buybacks and reinvestment. A cash balance of about $344 million and an expanded credit facility underscore liquidity.

Strong Market Position & Advantage: A 14‑state footprint with 110+ RISE dispensaries and leading brands (e.g., RYTHM, Dogwalkers, incredibles) positions the company among the top U.S. MSOs by scale and execution. External recognition like inclusion on TIME’s America’s Best Companies 2026 further reflects standing in the competitive set.

LeafyQuick
Cannabis • eCommerce • Logistics • On-Demand
Chicago
2 Employees
LeafyQuick is the Amazon of CBD Products, helping brands and consumers get the product need quickly!

LeafyQuick is the first and only same day CBD Delivery platform. Consumers can shop via an eCommerce platform a curated set of CBD products and have them delivered to their door. Brands work with LeafyQuick for all their fulfillment and last mile logistics services.

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LeafyQuick
Leaf Trade
Cannabis • eCommerce • Marketing Tech
Chicago
49 Employees

Leaf Trade is the leading wholesale marketplace between cultivators/processors and dispensaries in the highly regulated cannabis states. Leaf Trade streamlines order management and fulfillment by providing a CRM, essential integrations, and other tools that save time and help grow your business. Are you a retailer or vendor? Request a demo at: https://leaf.trade Looking to partner as an investor? Email us at http://leaf.trade/contact/

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Leaf Trade
4Front Ventures
8 Offices
98 Employees
9 Benefits

4Front (CSE: FFNT) (OTCQX: FFNTF) is a national multi-state cannabis operator and retailer, with a market advantage in mass-produced, low-cost quality branded cannabis products. 4Front manufactures and distributes a portfolio of over 25 cannabis brands including Marmas, Crystal Clear, Funky Monkey, Pebbles, and the Pure Ratios wellness collection, distributed through retail outlets and their chain of strategically positioned Mission branded...

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4Front Ventures
MedMen
Cannabis
15 Offices
509 Employees
15 Benefits

MedMen Enterprises is a leading cannabis company in the U.S. with assets and operations nationwide. MedMen owns and operates licensed cannabis facilities in cultivation, manufacturing and retail, and is the most recognized cannabis brand in the world today. MedMen brings class leading operational expertise and unprecedented investment to the fast changing and fast-growing cannabis industry as it moves from its gray...

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MedMen
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Grassroots Cannabis
Chicago
66 Employees

We’re Grassroots, a new cannabis company that’s all about living deeply. We started in Illinois and we’re growing nationally from the ground up. We care deeply, about our plants, our products and the people they serve. Our team brings an unmatched depth of expertise and commitment to perfection to every cannabis seedling we cultivate, and every product we invent. We...

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Grassroots Cannabis
Revolution Cannabis
Chicago
141 Employees

Revolution is a craft cannabis company. We lead the cannabis industry through scientific discovery and continuous innovation. As we grow to serve new communities, we bring our meticulous cultivation and operating standards to every new market and product we release. We love the cannabis plant and the cannabis industry. We strive to advance this industry, while maintaining its soul and...

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Revolution Cannabis
Track & Trace Tools
Cannabis • Productivity • Software • Business Intelligence • Agriculture
Fully Remote
Supercharge your Metrc workflow at a price your business can afford.

Track & Trace Tools (T3) is a powerful companion platform designed to streamline compliance and operational efficiency for businesses using Metrc, the industry-standard seed-to-sale tracking system. T3 enhances the Metrc experience by providing intuitive tools for scanning, searching, and managing inventory with speed and accuracy. Whether you’re tracking plant batches, monitoring package transfers, or verifying compliance data, T3 simplifies complex...

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Track & Trace Tools
Fringe
HR Tech
2 Offices
120 Employees
29 Benefits Hiring Now

Fringe is the world’s first Wellbeing Marketplace. With Fringe, employers save money by consolidating their employee experience programs into one platform to recruit and retain talent. Fringe has hundreds of services and experiences intelligently designed to drive business outcomes and employee wellbeing. To learn more, check us out at fringe.us

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Fringe

Fringe's Top Stability & Growth Strengths

Strategic Partnerships: An announced ADP Workforce Now embed, ADP Marketplace presence, and partner-led distribution (including Alight) expand access and visibility within established HR ecosystems. These ties are presented as meaningful go-to-market advantages and evidence of deepening channel strength.

Product Line Growth: The launch of "Fringe 2.0" broadened the platform from LSAs into recognition, rewards, wellbeing, learning, swag, and gifting. This expansion signals ongoing investment and a move to consolidate multiple point solutions.

Market Expansion: Public communications highlight broadened availability and active rollouts through large ecosystems. Distribution embeds and partner marketplaces indicate an expanding footprint across buyer segments and geographies.

Spark'd Dispensary
Cannabis • Information Technology • Retail
5 Offices
39 Employees

Recreational dispensaries in Illinois ? Step into a welcoming atmosphere where likeminded individuals gather to enjoy and explore the wonders of cannabis. Our mission is to create a safe, inclusive, and educational space for cannabis enthusiasts and the canna-curious.

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Spark'd Dispensary
CannaTrac
Cannabis • Payments
Chicago

CannaTrac® offers a cashless payment solution for the cannabis industry. With the CannaCard® or our CannaCard App™, both consumers and retailers benefit from the ease and safety of cashless payments.

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CannaTrac
Kifcure
Cannabis
Maple Park
10 Employees
We create a “Full-Spectrum” approach to the hemp supply chain.

Kifcure is where “Vision meets Dreams in the Hemp Industry.” We take hemp from seed, to soil, to oil. We are involved in every step of the process with farmers and brands making their way in the hemp industry. The company is positioned to be at the cutting edge of the explosion of this relatively new market and all its...

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Kifcure
PharmaCann
Cannabis
Chicago
499 Employees
22 Benefits Hiring Now

PharmaCann, founded in 2014, is one of the country’s largest vertically integrated cannabis companies, providing safe, reliable, top-quality cannabis products to improve people’s lives. By investing in people, practices and infrastructure, we are shaping a new, vital, wellness-focused industry. Our goal is to increase sustainable access to cannabis by offering effective, affordable and trusted products and services. We are licensed...

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PharmaCann
Silver Star Protection Group
Cannabis • Professional Services • Security • Consulting

Silver Star Protection Group is a fully integrated security partner that combines physical protection, advanced security technology, secure transport, and risk consulting to protect assets and people.

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Silver Star Protection Group
bswift
Healthtech • Software
2 Offices
750 Employees
43 Benefits

bswift is a Chicago-based technology company that provides benefits administration for employers and exchanges nationwide. We pride ourselves on having a fun, friendly and smart staff that goes the extra mile to get the job done right. The reward is a fun, flexible and creative environment with ample opportunity for growth.

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bswift

bswift's Top Stability & Growth Strengths

Customer Loyalty & Retention: Feedback suggests clients remain with bswift at high rates, with reference stories citing strong satisfaction and outcomes in complex environments. This persistence indicates a durable customer base supporting stability.

Innovation-Driven Growth: Feedback suggests a steady cadence of product advances—AI-native Emma capabilities, new analytics dashboards, and a rapidly adopted mobile app—driving usage and differentiation. Multiple recent industry awards for benefits innovation reinforce momentum.

Strategic Partnerships: Selection as ASHHRA’s preferred benefits administration partner and new alliances point to expanding distribution and credibility. Such relationships can accelerate access to targeted sectors like healthcare.

Verano
Cannabis
2 Offices
202 Employees

Verano™ is a national, vertically-integrated operator of licensed cannabis cultivation, manufacturing, and retail facilities dedicated to improving lives by providing safe access to effective organic cannabis products that enhance health and wellness and by positively impacting the communities it serves. Verano develops and produces a well-rounded suite of limited edition, fashion-forward cannabis products, which offer superior medicinal therapies and inspirational...

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Verano

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