Best Retail Companies in Chicago, United States
The 538 best Retail companies in Chicago, United States in 2026, ranked by funding and momentum. Funding, investors, founders, valuation, tech stack and live signals. Top: Groupon.
Ranked: Best Retail companies in Chicago
| # | Company | Disclosed funding | Last round | Employees | Founder | Tech stack | Patents & IP focus | Recent signals |
|---|---|---|---|---|---|---|---|---|
| 1 | Groupon Online marketplace offering deals on multi-category products and services | $950M | 185 mo ago | 1,582 | Eric Lefkofsky Co-Founder | TurbopackSentryZendesk+35 | 1,437 patents Online deal marketing analytics and personalized recommendation systems for e‑commerce | — |
| 2 | ShipBob 🦄 Provider of e-commerce fulfillment solutions for direct-to-consumer brands | $333M | 59 mo ago | 1,338 1,338 → 1,665 (+24%) · sector median +17% | Dhruv Saxena Co-Founder & CEO | WordPress Block EditorWordPressApple iCloud Mail+38 | — | 1 award |
| 3 | GTI Provider of health, and wellbeing products related to cannabis | $225M | 84 mo ago | 4,600 4,600 → 2,363 (-49%) · sector median +17% | — | DrupalApple iCloud MailPHP+26 | 4 patents Modular, expandable portable shelter systems for temporary housing and emergency structures. | — |
| 4 | Cameo 🦄 Online platform offering personalized video messages from celebrities | $191M | 18 mo ago | 301 301 → 353 (+17%) · sector median +17% | Martin Blencowe Co-Founder | Apple iCloud MailGoogle WorkspaceGoogle Sign-in+29 | — | — |
| 5 | Raise Online marketplace offering gift cards for cash | $140M | 15 mo ago | 74 | — | Apple iCloud MailGoogle WorkspaceMUI+19 | — | — |
| 6 | Provi Operator of an online marketplace connecting alcohol buyers, distributors, and brands | $139M | 32 mo ago | 249 | Taylor Katzman Founder & CEO | HubSpot CMS HubApple iCloud MailGoogle Workspace+26 | — | — |
| 7 | Verano Provider of cannabis-based products for health and wellbeing | $120M | 63 mo ago | 3,780 | George Archos Co-Founder | DrupalPHPAmazon Web Services+28 | 4 patents Network security event monitoring and large-scale data scanning for alerts | — |
| 8 | Cresco Labs Brand & retailer of cannabis gummies, seeds, and other products | $104M | 92 mo ago | 2 | — | WordPressApple iCloud MailMySQL+21 | 7 patents Cannabis extraction, oil purification/fractionation, and agricultural risk management analytics. | — |
| 9 | Circana Customer analytics solutions for brands and retailers | $100M | 180 mo ago | 6,400 6,400 → 6,219 (-3%) · sector median +17% | Kirk Perry CEO | WixSentryApple iCloud Mail+27 | — | — |
| 10 | Cooler Screens Developer of IoT enabled solution for the retail businesses | $100M | 68 mo ago | 74 | — | — | 43 patents AI-powered inventory, marketing, and advertising system for refrigerated retail storage containers | — |
| 11 | PowerReviews Cloud-based platform to generate insights on reviews | $91M | 67 mo ago | 121 121 → 81 (-33%) · sector median +17% | Mark Dillon CEO | WordPressApple iCloud MailGoogle Workspace+36 | 20 patents E‑commerce product review generation, analysis, and dynamic summary tools for online retailers. | — |
| 12 | Farmer's Fridge Provider of food vending machines | $83M | 62 mo ago | 212 212 → 428 (+102%) · sector median +17% | Luke Saunders Founder & CEO | ShopifyCart FunctionalityContentful+20 | — | 1 job opening · 2 awards |
| 13 | Braintree Payment gateway solutions | $69M | 164 mo ago | 183 | Brain CEO | — | — | — |
| 14 | ThreeKit AR-based product visualization platform for the retail industry | $66M | 55 mo ago | 86 | Ben Houston CTO & Founder | HubSpot CMS HubApple iCloud MailGoogle Workspace+22 | — | 1 partnership |
| 15 | Revolution Provider of cannabis based products for medicine | $63M | 46 mo ago | 110 | — | WordPressApple iCloud MailMySQL+29 | 27 patents Personalized digital health program platforms with interactive UI and safe passenger transport systems | — |
| 16 | Tovala Provider of connected smart ovens | $61M | 64 mo ago | 350 | David Rabie Co-Founder & CEO | Amazon WebstoreCart FunctionalitySentry+41 | 2 patents Smart kitchen appliance automation and optimized perishable food packaging solutions | — |
| 17 | InContext Solutions Provider of 3D virtual store platforms and retail execution solutions | $54M | 65 mo ago | 77 77 → 62 (-19%) · sector median +17% | Dave Rich Chairman & CEO | Master SliderSlider RevolutionWordPress+23 | 12 patents Virtual reality retail visualization and 3D apparel scanning for e‑commerce | — |
| 18 | Retale Aggregator of offline flyers, coupons and catalogs | $45M | 122 mo ago | 120 | — | — | — | — |
| 19 | Sittercity Marketplace platform for caregivers | $43M | 150 mo ago | 38 | — | ContentfulTailwind CSSEnvoy+12 | — | — |
| 20 | Black Buffalo Internet first brand offering nicotine patches | $38M | 46 mo ago | 18 | Mark Hanson President and Co-Founder | Shogun Page BuilderCart FunctionalityShopify+44 | — | — |
| 21 | Rheaply SaaS-driven procurement management software | $35M | 14 mo ago | 71 | Garry Cooper Co-Founder & CEO | WordPressApple iCloud MailGoogle Workspace+35 | — | — |
| 22 | Fooda Provider of workplace food programs featuring pop-up restaurants and catering | $32M | 33 mo ago | 223 | Shane Jones Co-Founder | DrupalApple iCloud MailMicrosoft 365+27 | — | 1 award |
| 23 | Interior Define Internet-first brand of custom made furniture | $26M | 53 mo ago | 79 | — | MagentoCart FunctionalitySkolengo+58 | — | — |
| 24 | Monica + Andy Organic baby clothes, blankets, pajamas, and more for families | $26M | 48 mo ago | 58 | Brian Bloom Co-Founder & CFO | ShopifyTailwind CSSAmazon Web Services+32 | — | — |
| 25 | ItemMaster Cloud-based product content creation and management platform for the food and beverage marketplace | $25M | 98 mo ago | 75 | Simon Angove CEO | — | — | — |
| 26 | ShoppingGives Provider of cashback management solutions for businesses | $24M | 47 mo ago | 47 | Ronny Sage Founder & CEO | — | — | — |
| 27 | Leaf Trade A wholesale cannabis marketplace platform | $23M | 50 mo ago | 52 | Steve Weisman Co-Founder & Chairman | WordPressMySQLPHP+23 | — | — |
| 28 | Crafty Online B2B marketplace offering multi-category grocery products for offices 67Funding top 25%Growth top 26%Talent top 28%Innovation top 34% All 10 signals ▾Fundingtop 25% Growthtop 26% Talenttop 28% Innovationtop 34% Producttop 36% Techtop 39% Moattop 39% Markettop 49% Globalbottom 32% Customersbottom 1% Funding: Raised $21.6M across 8 rounds · 8 rounds over 8 yrs (1.0/yr) Growth: Headcount 74 → 116 (+57%) across vintages · Fresh capital in last 24 mo rank vs industry peers · Fliar Intelligence Index 67/100 | $22M | 3 mo ago | 116 116 → 256 (+121%) · sector median +17% | Nathan Rosenstock Co-Founder | WordPressMySQLPHP+29 | — | 1 launch |
| 29 | LandscapeHub Online marketplace for landscaping materials | $19M | 28 mo ago | 46 | — | Cart FunctionalityRubyVimeo+27 | — | — |
| 30 | SalonInteractive Provider of online retail and marketing tools for beauty professionals | $17M | 29 mo ago | 21 | — | RubyErlangSalesforce+22 | — | — |
| 31 | Brideside Platform for finding and buying wedding dresses | $14M | 73 mo ago | 110 | — | — | — | — |
| 32 | Goose Provider of business management solutions for pet care platforms | $13M | 15 mo ago | 6 | — | WebflowRiveAmazon Web Services+23 | — | 1 job opening · 1 launch |
| 33 | Venzee Provider of product information management and content syndication platform | $13M | 47 mo ago | 32 | — | — | — | — |
| 34 | The 1937 Group Brand of cannabis products | $13M | 45 mo ago | 13 | Ambrose Jackson Chairman and CEO | Wix eCommerceWixSentry+12 | — | — |
| 35 | Purchasing Platform Provider of software suite solutions for businesses | $13M | 43 mo ago | 41 | Dave Bowen CEO | — | — | — |
| 36 | Oars + Alps Internet first brand offering beauty care products for men | $12M | 24 mo ago | 14 | Mia Saini Duchnowski CEO and Co-Founder and Board of Director | Cart FunctionalityShopifySentry+57 | — | 1 award |
| 37 | Pacas Internet first brand offering socks for men, women and kids | $11M | 36 mo ago | 26 | Christian Arquilla Co-Founder | Cart FunctionalityShopifyBugHerd+36 | — | — |
| 38 | Nurture Life Internet first brand offering subscription based cooked meals for kids | $7M | 29 mo ago | 50 50 → 67 (+34%) · sector median +17% | Helen Revans Founder of Nurture Your Life | Amazon WebstoreCart FunctionalityZoho+41 | — | 2 awards |
| 39 | Coldcart Provider of technology platform optimizing perishable parcel and eCommerce logistics | $6M | 23 mo ago | — | Andrew Salamon Co-Founder | — | — | — |
| 40 | Listener Brands Internet first brand offering hair care and styling products | $6M | 15 mo ago | 30 | Kim Lewis Co-Founder | — | — | — |
| 41 | Vibe IQ Providing brands with go-to-market collaborative retail applications | $6M | 24 mo ago | — | Brian Lindauer Founder | WordPressMySQLPHP+25 | 8 patents Interactive digital signage and personalized media delivery with liquid-activated illumination systems | — |
| 42 | Pimly Provider of product information management solutions for e-commerce businesses | $5M | 11 mo ago | 14 | — | — | — | 1 launch |
| 43 | Public Rec Internet first brand offering casual wear for men and women | $5M | 33 mo ago | 27 | — | ShopifySentryZendesk+39 | — | — |
| 44 | Tradepost Operator of platform facilitating instant offers for various collectible items | $5M | 8 mo ago | — | Alexander Perez Co-Founder & CTO | Node.jsTypeScriptGraphQL+12 | — | — |
| 45 | Zenblen Provider of tech-enabled smoothie bar | $3M | 10 mo ago | 10 | Tom Zhang Founder & CEO | Cart FunctionalityWix eCommerceWix+14 | — | — |
| 46 | Neopenda Provider of wearable neonatal signs monitor 16Moat top 38%Funding top 42%Tech top 43%Talent bottom 49% All 12 signals ▾Moattop 38% Fundingtop 42% Techtop 43% Talentbottom 49% Productbottom 47% Growthbottom 43% Globalbottom 37% Innovationbottom 36% Patentsbottom 25% Marketbottom 22% Fin. healthbottom 19% Newsbottom 18% Moat: Editorial + unicorn rating 7/10 · IP moat: 3 patents Funding: Raised $2.7M across 12 rounds · 12 rounds over 8 yrs (1.5/yr) rank vs industry peers · Fliar Intelligence Index 16/100 | $3M | 1 mo ago | 14 | Teresa Cauvel Co-founder and CTO | WixSentryBootstrap+14 | 3 patents Wearable neonatal vital‑sign monitoring systems | 1 job opening · 1 launch · 1 expansion |
| 47 | Continuum Provider of B2B automated returns software for wholesale organizations | $2M | 6 mo ago | — | Alex Witcpalek Founder & CEO | HubSpot CMS Hubcore-jsPreact+14 | 13 patents Patents concentrated in electrical & electronics | 3 job openings |
| 48 | IN BOLD PRINT Provider of SaaS-based sustainability scoring platform on website for brands and retailers | $2M | 20 mo ago | 6 | Ashley Pradhan Co-Founder & Co-CEO | — | — | — |
| 49 | TrustClarity Provider of SaaS-based excess inventory management solution | $300K | 14 mo ago | 5 | Sujee Jeganathan Founder & CEO | Node.jsBootstrapExpress+19 | 2 patents Patents concentrated in computing, sensing & instrumentation | 1 job opening |
| 50 | DUDE Wipes Online platform offering personal hygiene wipes for men | $225K | 11 mo ago | — | Jeffrey Klimkowski Co-Founder and CFO | Cart FunctionalityAmazon WebstoreShopify+28 | — | — |
Top 12 Retail companies in Chicago
#1
Series B · Chicago, Illinois · founded 2015 · 116 employees$21.6Mraised▾
Online B2B marketplace offering multi-category grocery products for offices. It caters to offices to manage pantries, catering, cafes, etc. The product catalog includes hot coffee, cold brew coffee, kegs, craft beer, dry snacks, breakfasts, etc.
- Feb 2026Series B$13.2M
- Nov 2025Series A$1M
- May 2024Series A$8.7M
- Apr 2022Series A$10M
#2
Seed · Chicago, Illinois · founded 2015 · 14 employees$2.7Mraised▾
Provider of wearable neonatal signs monitor. The device is a small low-cost neonatal vital signs monitor integrated into a baby hat and uses a simple sensor array to measure heart rate, respiratory rate, blood oxygen saturation, and temperature. The sensors are powered by rechargeable batteries, and wirelessly transmit data to a central monitor which alerts attending healthcare professionals when a newborn is in immediate danger. It is intended for critically ill newborns being cared for in hospitals in low-resource countries such as Uganda.
- Apr 2026Conventional Debt$35K
- Nov 2024Conventional Debt$200K
- Sep 2022Conventional Debt$700K
- Apr 2021Seed$1.4M
#3
Series D · Chicago, Illinois · founded 2011 · 74 employees$140.2Mraised▾
Online marketplace offering gift cards for cash. It allows users to sell gift cards from different brand and restaurant to get cash back. The user chooses the selling price and the gift card is featured on its for consumers to buy.
- Feb 2025Series D$63M
- Sep 2017Series C$60M
- Jun 2016Series B$818.3K
- Jan 2015Series B$56M
#4
Cameo 🦄Series C · Chicago, Illinois · founded 2017 · 301 employees$190.8Mraised▾
Online platform offering personalized video messages from celebrities. It enables users to book personalized video shoutouts from their favorite celebrities, sportsmen, influencers, and more. It also allows users to download videos and share them across their social media pages.
- Dec 2024Series C$2.9M
- Mar 2024Series C$25.1M
- Mar 2021Series C$100M
- Jun 2019Series B$50M
#5
Series B · Chicago, Illinois · founded 2016 · 71 employees$35.5Mraised▾
SaaS-driven procurement management software. The company offers 'Rheaply AxM' - an online inventory management software, which enables organizations to lower procurement and storage costs and manage their assets. Features include automated listings, automated notification & messages, and automated reporting.
- Apr 2025Series B$1M
- Mar 2023Series B$15.2K
- Jun 2022Series B$20M
- Dec 2021Grant (prize money)$100K
#6
Series A · Chicago, Illinois · founded 2024$4.6Mraised▾
Operator of platform facilitating instant offers for various collectible items. The platform allows users to sell tickets, sports cards, trading cards, sealed wax, autographs, sneakers, vinyl, comic books, magazines, consoles, and video games. It also supports the sale of smartphones, handbags, designer clothes, streetwear, watches, laptops, Labubu, coins, Legos, jewelry, and vintage items. Furthermore, the platform facilitates transactions for books, eyewear, fine wine, stamps, bobbleheads, cars, domains, fine art, condos, and startups.
- Sep 2025Series A$4.6M
#7
Series A · Chicago, Illinois · founded 2023$1.7Mraised▾
Provider of B2B automated returns software for wholesale organizations. It manages continuous transactions post purchase order for wholesale, distribution, and manufacturing organizations. It offer services such as touchless RMA automation, updates on return status, and integrations with business system.
- Dec 2025Series A$7.2M
- Nov 2024Seed$4.1M
- Apr 2024Seed$1.7M
#8
Series A · Chicago, Illinois · founded 2022 · 14 employees$5Mraised▾
Provider of product information management solutions for e-commerce businesses. The solutions provided are real-time product information & image management, configurable digital catalogs, sell sheets, and more. The platform connects the sellers PIM to their Salesforce customer relationship management segment.
- Jul 2025Series A$2.3M
- Sep 2022Series A$5M
#9
Seed · Chicago, Illinois · founded 2021 · 6 employees$13.4Mraised▾
Provider of business management solutions for pet care platforms
- Feb 2025Seed$13.4M
#10
Seed · Chicago, Illinois · founded 2018 · 10 employees$2.8Mraised▾
Provider of tech-enabled smoothie bar. It enables users to order using the touchscreen interface and make payments.
- Aug 2025Seed$2.5M
- Sep 2023Seed$2.8M
#11
Deadpooled · Chicago, Illinois · founded 2015 · 30 employees$6.4Mraised▾
Internet first brand offering hair care and styling products. Its product catalog includes shampoo, conditioner, styling cream, moisturizer, flaxseed gel, and serum. It also offers personalized recommendations based on hair type and condition.
- Feb 2025Series A$200K
- Jun 2023Series A$1M
- May 2023Series A$5M
- Nov 2022Seed$450K
#12
Series C · Chicago, Illinois · founded 2015 · 249 employees$138.8Mraised▾
Operator of an online marketplace connecting alcohol buyers, distributors, and brands. The platform provides tools for product discovery, communication, and order management. It offers a way for buyers to find products and connect with sales representatives. The platform also allows brands and distributors to showcase portfolios.
- Oct 2023Series C$32.5M
- Sep 2021Series C$75M
- 2021Series B$25M
- May 2018Seed$4.8M
Funding & investor landscape
Notable founders
Market landscape — 10 sub-themes by coverage
Share of Retail coverage by sub-theme.
Regulatory-risk over time rising
Funding & growth over time
funding rising · growth rising