Best Internet First Media Companies in Chicago, United States
The 66 best Internet First Media companies in Chicago, United States in 2026, ranked by funding and momentum. Funding, investors, founders, valuation, tech stack and live signals. Top: The Athletic.
Ranked: Best Internet First Media companies in Chicago
| # | Company | Disclosed funding | Last round | Stage | Founder | Founded | Tech stack | Patents & IP focus | Recent signals |
|---|---|---|---|---|---|---|---|---|---|
| 1 | The Athletic Online sports media company | $140M | 77 mo ago | Acquired | Adam Hansmann Co-Founder & President | 2016 | — | 19 patents Integrated sports protective apparel and equipment for impact mitigation | — |
| 2 | Tastytrade Online platform publishing content focusing on investment | $60M | 95 mo ago | Acquired | Tom Sosnoff Co-Founder & CEO | 2011 | ContentstackSentrySalesforce+37 | 10 patents Mobile securities trading and real-time aggregated market/educational data platform | — |
| 3 | Dose A media company that creates and distributes viral content | $34M | 126 mo ago | Series B | — | 2009 | Node.jsGoogle CloudExpress+8 | — | — |
| 4 | NileGuide Local travel guides for planning trips to global destinations | $12M | 184 mo ago | Acquired | Josh Steinitz Founder & CEO | 2006 | NginxjQuery UIjQuery+5 | — | — |
| 5 | Here Real estate investment and deal recommendation firm | $7M | 47 mo ago | Seed | — | 2010 | BeehiivSentryHeadless UI+17 | 94 patents AI-driven dynamic object detection and location-based content management systems | — |
| 6 | EQDerivatives News and research platform for investors | $1M | 85 mo ago | Seed | Rob Mcglinchey Managing Director & Co-Founder | 2014 | WordPress Block EditorWordPressApple iCloud Mail+17 | — | — |
| 7 | TransFS Digital information platform for personal finances | $510K | 190 mo ago | Seed | Sean Harper CEO | 2009 | — | — | — |
| 8 | Windy City Media Network Online platform offering multi-category news | $303K | 170 mo ago | Deadpooled | Brett Rosin Co-Founder & CEO | 2010 | — | — | — |
Top 10 Internet First Media companies in Chicago
#1
Seed · Chicago, Illinois · founded 2010 · 44 employees$7Mraised▾
Real estate investment and deal recommendation firm. This company identifies and delivers daily email updates featuring promising Airbnb investment properties across various property types and price points. The service focuses on providing detailed information to facilitate informed investment decisions. The recommendations are categorized for easier navigation and selection based on investor preferences. It has also acquired, designed, and managed a portfolio of some of the most enchanting Airbnb investment properties across the United States.
- Jul 2022Seed$5M
- Mar 2022Seed$2M
#2
Acquired · Chicago, Illinois · founded 2016 · 433 employees$139.5Mraised▾
The Athletic is a subscription-based, local-focused sports media brand targeting the premium fan segment. The Company claims to provide the most credible insider information in sports media by combining privileged locker room access with a deep reliance on analytics.The company is currently focused in two markets, Chicago and the San Francisco Bay Area. It is backed by Precursor Ventures and Y Combinator.
- Jan 2020Series D$50M
- May 2019Series C$22M
- Oct 2018Series C$40M
- Mar 2018Series B$20M
#3
Acquired · Chicago, Illinois · founded 2011 · 156 employees$60.4Mraised▾
Online platform publishing content focusing on investment. It provides live broadcasts with financial information and publishes content focusing on investments. It features shows like market measures, good trade bad trade, and bootstrapping.
- Jun 2018Series B$20M
- Jun 2013Series A$7M
- May 2013Series A$699.6K
- Dec 2012Series A$2M
#4
Series B · Chicago, Illinois · founded 2009 · 53 employees$34.5Mraised▾
Dose Media is the company behind digital media properties Dose and OMG Facts. Dose claims that its predictive technology detects “stories worth sharing” i.e. it uses predictive technology to identify content that is likely to become a viral hit and then creates stories based off that information and passes it around social media. OMGFacts zeroes in on surprising factoids that also have a high potential to make waves online. Has over 50 MM unique visitors which amount 4 times growth in a year. Tribune Media in Dec 2015 led a $25 million round of investment in viral content sites Dose and OMGFacts.
- Dec 2015Series B$25M
- Oct 2013Series A$8M
- Jan 2013Seed—
- Jan 2012Seed$1.5M
#5
Funding Raised · Chicago, Illinois · founded 2017 · 15 employees$50Kraised▾
Online platform providing multi-category newsletters. The platform provides newsletters on sports, tech, culture, business, & more.
- Oct 2021Grant (prize money)$50K
#6
Acquired · Chicago, Illinois · founded 2006 · 2 employees$11.7Mraised▾
Local travel guides for planning trips to global destinations. This platform provides recommendations for exploring popular travel destinations worldwide. It offers local insights on the best things to do, hotels, restaurants, and attractions. Users can plan trips to various locations across North America, Europe, South America, the Caribbean, Oceania, Central America, Asia, and Africa. The service aims to provide a local perspective for travelers seeking authentic experiences. It is a resource for individuals looking to explore and discover new places with insider knowledge. The platform supports travel planning by offering curated information and recommendations.
- Feb 2011Venture Debt—
- Dec 2010Series C$3.5M
- Aug 2010Series B$200K
- Jun 2008Series B$8M
#7
Seed · Chicago, Illinois · founded 2014 · 19 employees$1.1Mraised▾
EQDerivatives provides news and research platforms for investors, portfolio managers, and service providers. It features strategies for volatility derivatives and alternative risk solutions. It offers events and news for buyers and sellers of equity and volatility derivatives.
- May 2019Seed$750K
- Jun 2014Seed$345K
#8
Seed · Chicago, Illinois · founded 2009$510Kraised▾
Digital information platform for personal finances
#9
Deadpooled · Chicago, Illinois · founded 2010$303Kraised▾
Online platform offering multi-category news. It provides news under various categories including politics, health, entertainment, business, economy, and others. It monetizes through display advertisements.
- Mar 2012Seed$303K
#10
Acquired · Chicago, Illinois · founded 1998 · 227 employees$25Kraised▾
Legacy.com is an online media network offering news focused on obituaries. It offers news based on various topics such as obituaries, funeral homes, memorials, and more. Also operates "Tributes.com", which offers local and national obituary news. Also allows users to search for obituaries and funeral homes based on cities. Monetizes through display ads.
- Jan 2018Unattributed$25K
- Jun 2000Series A—
Funding & investor landscape
Notable founders
Market landscape — 10 sub-themes by coverage
Share of Internet First Media coverage by sub-theme.
Regulatory-risk over time rising
Funding & growth over time
funding rising · growth rising
Common questions
Rohit lives in the feed. He covers what's moving right now — the funding rounds, launches and shifts breaking across the trade press — and ties them back to where the sector is heading.