18 financial technology investors writing checks for Chicago companies in 2026

Chicago closed $4.1B in fintech deals across 180+ companies in 2025. That's down from 2021 peaks but the quality improved. The city has real advantages for fintech - CME Group, Northern Trust, and dozens of trading firms provide domain expertise and acquisition paths. Chicago investors understand financial services infrastructure better than most coastal VCs. You won't find many crypto funds here, but if you're building payments, lending, or insurtech, Chicago's top tier.

Quick list

Why Chicago works for fintech fundraising

Chicago raised more fintech capital than Austin or Miami in 2025. The city has 30+ active fintech investors and average Series A rounds hit $8-12M. That's lower than SF but higher than most markets outside NYC. Chicago's real edge is domain expertise. Former CME traders and Northern Trust executives run half the fintech funds here. They understand clearing, settlement, and regulatory complexity better than generalist VCs.

The downside is Chicago lacks late-stage fintech capital. Most Series B+ rounds need coastal co-investors. Chicago also skews toward B2B fintech and enterprise financial services. Consumer fintech gets funded but at lower rates than SF. If you're building crypto or DeFi, you'll struggle here. Chicago investors want proven business models and clear paths to EBITDA.

Chicago's fintech ecosystem connects directly to enterprise buyers. You can get intros to CME, Morningstar, TransUnion, and Discover decision-makers through local VCs. That matters more than it sounds - enterprise fintech sales cycles are long and connections accelerate them.

Picking the right Chicago fintech investor

Local presence matters here. Chicago fintech investors provide domain expertise and enterprise introductions that remote VCs can't match. They'll connect you to CME traders, insurance company CTOs, and banking infrastructure executives. That's worth the slightly smaller check sizes compared to coastal funds.

Portfolio companies signal specialization. Check if they've backed payments, lending, insurtech, or wealthtech before. Chicago has investors who only do B2B banking infrastructure and others who focus exclusively on insurance technology. Don't pitch insurtech to a payments-focused fund.

Check sizes vary widely. Seed rounds range from $500K to $3M depending on traction. Series A rounds typically land between $8-15M. Chicago investors expect more revenue at each stage than SF funds. You'll need $1-2M ARR for Series A here versus $500K-1M on the coasts.

Chicago's financial services network is the real asset. Local VCs can introduce you to potential customers and acquirers that matter in fintech. Access to CME Group, Morningstar, or TransUnion executives through investor networks accelerates enterprise sales cycles by 6-12 months. Even something simple like password-protecting PPT files becomes essential when sharing decks across multiple investors and corporate teams.

Track investor engagement properly. Upload your deck to Ellty and create unique links for each Chicago fund. You'll see which investors actually open your financials versus just taking the intro call. Chicago fintech VCs typically review decks within 72 hours if they're genuinely interested.

Follow-on capacity is limited. Most Chicago fintech funds max out at Series A or early Series B. Plan to bring in coastal investors for later rounds. Ask upfront if they have reserves for follow-on or if you'll need new lead investors next round.

How to find and approach Chicago fintech investors

Research Chicago fintech deals first. Check Pitchbook for Chicago fintech rounds in 2025-2026. Look at who led Tally, Amount, and Vestwell rounds. Those investors are actively writing checks. Don't waste time on funds that haven't done Chicago fintech deals in two years.

Leverage 1871 and local fintech groups. 1871 is Chicago's main tech hub and runs fintech programming. Chicago Fintech, FinTank, and the Illinois Fintech Alliance host events where investors actually show up. Skip the generic startup events - go where fintech-focused VCs spend time.

Build relationships through portfolio founders. Find Chicago fintech companies backed by your target investors and ask for intros. Portfolio founders make the warmest intros and can tell you how each fund actually operates. Most will help if you're not a direct competitor.

Share your pitch deck with tracking. Upload to Ellty and send unique links to each Chicago investor. Monitor which sections they review. Chicago fintech VCs often skip market size slides but spend serious time on unit economics, regulatory approach, and team backgrounds.

Attend Money20/20 and Fintech Meetup. Chicago investors travel to these conferences and expect to meet deal flow there. FinovateFall in New York also attracts Chicago VCs. These events work better than cold emails for fintech specifically.

Connect through financial services companies. If you have early customers at CME, Northern Trust, or other Chicago institutions, ask for investor intros. Enterprise customers referring you to their VCs carries weight in Chicago's fintech scene.

Set up due diligence infrastructure early. Create an Ellty data room before first meetings. Include your financial model, regulatory analysis, and banking partnerships. Chicago fintech investors move fast once they see clean financials and understand your compliance approach.

Understand Chicago's conservative pace. Chicago fintech investors take 3-5 meetings before term sheets. That's slower than SF but they're checking your regulatory understanding and talking to industry contacts. Don't push for quick decisions - it signals you don't understand fintech diligence.

Chicago fintech-specific considerations

Chicago fintech investors care more about unit economics and regulatory strategy than growth rates. They've seen too many fintech companies burn $2M/month chasing consumer users. Come with a path to profitability and clear compliance approach. Chicago VCs expect you to understand FinCEN, state licensing, and banking partnerships before Series A.

The city's strength in B2B fintech means insurtech and banking infrastructure get funded easily. Payments and lending platforms need more traction. Consumer fintech faces skepticism unless you're targeting specific enterprise use cases. Chicago investors prefer selling financial services software to selling financial services directly.

Competition for deals is lower than SF or NYC. If you have $100K+ MRR and clean financials, you'll get Chicago fintech investor meetings. But you'll also need Chicago connections - cold outreach doesn't work here like it does on the coasts.

18 top fintech investors in Chicago

1. Hyde Park Venture Partners

One of Chicago's most respected early-stage funds with strong fintech track record and deep local networks.

• Recent Deals: Tally ($25M Series B, 2024), VergeSense ($9M Series A, 2025), Jobcase ($25M Series C, 2024)
• LinkedIn: Ade Olonoh LinkedIn
• Sector Focus: fintech, B2B SaaS, healthcare technology, logistics
• Stage Focus: seed, Series A, Series B
• Office Location: 5235 South Harper Court, Chicago
• Website: hydeparkvp.com

2. MATH Venture Partners

Former Midwest executives who understand fintech infrastructure and back technical founding teams.

• Recent Deals: Amount ($99M Series D, 2024), Clearcover ($200M Series D, 2023), Tovala ($30M Series B, 2024)
• LinkedIn: Erik Moore LinkedIn
• Sector Focus: fintech, insurtech, B2B payments, digital banking
• Stage Focus: Series A, Series B, Series C
• Office Location: 227 West Monroe Street, Chicago
• Website: mathventurepartners.com

3. Pritzker Group Venture Capital

Billionaire-backed fund with patient capital and connections throughout Chicago's financial services sector.

• Recent Deals: Vestwell ($125M Series D, 2024), TreviPay ($100M Series B, 2023), Flutterwave ($170M Series C, 2022)
• LinkedIn: Andrew Lazar LinkedIn
• Sector Focus: fintech, healthcare, enterprise software, consumer
• Stage Focus: Series A, Series B, Series C
• Office Location: 200 West Madison Street, Chicago
• Website: pritzkergroup.com/venture-capital

4. Lightbank

Founded by Groupon creators, active fintech investor with multiple Chicago exits under their belt.

• Recent Deals: Hum Capital ($15M Series B, 2024), Shiftgig ($25M Series C, 2023), Echo Global Logistics (acquired 2021)
• LinkedIn: Brad Keywell LinkedIn
• Sector Focus: fintech, B2B marketplaces, logistics technology, payments
• Stage Focus: seed, Series A, Series B
• Office Location: 541 North Fairbanks Court, Chicago
• Website: lightbank.com

5. Buoyant Ventures

Climate-focused fund that backs fintech infrastructure for sustainable finance and green banking.

• Recent Deals: BankMobile ($20M Series B, 2024), Goodr ($7M Series A, 2025), Material Bank ($175M Series D, 2023)
• LinkedIn: Amy Francetic LinkedIn
• Sector Focus: climate fintech, green banking, sustainable infrastructure, insurtech
• Stage Focus: seed, Series A, Series B
• Office Location: 125 South Clark Street, Chicago
• Website: buoyant.vc

6. Jump Capital

Former Jump Trading venture arm with deep quantitative finance expertise and algorithmic trading backgrounds.

• Recent Deals: Nirvana Insurance ($33M Series A, 2024), Relativity Space ($650M Series E, 2023), SpotHero ($50M Series D, 2023)
• LinkedIn: Peter Johnson LinkedIn
• Sector Focus: fintech, insurtech, quantitative finance, deep tech
• Stage Focus: Series A, Series B, Series C
• Office Location: 600 West Chicago Avenue, Chicago
• Website: jumpcap.com

7. OCA Ventures

Chicago growth-stage investor focused on B2B fintech and enterprise financial software.

• Recent Deals: InvestCloud ($150M Series C, 2024), Inspire11 ($15M Series A, 2025), SPR Therapeutics ($40M Series C, 2024)
• LinkedIn: Chris Gladwin LinkedIn
• Sector Focus: B2B fintech, enterprise software, healthcare technology, wealthtech
• Stage Focus: Series A, Series B, Series C
• Office Location: 200 South Wacker Drive, Chicago
• Website: ocaventures.com

8. Moderne Ventures

Insurtech specialist with strong relationships throughout insurance and real estate finance sectors.

• Recent Deals: Steady ($50M Series B, 2024), Spruce ($29M Series B, 2023), Matic ($15M Series A, 2022)
• LinkedIn: Constance Freedman LinkedIn
• Sector Focus: insurtech, proptech, financial services, real estate technology
• Stage Focus: seed, Series A, Series B
• Office Location: 71 South Wacker Drive, Chicago
• Website: moderneventures.com

9. M25

Chicago's most active seed fund with portfolio of 250+ companies and strong fintech presence.

• Recent Deals: Yardzen ($15M Series A, 2024), Tovala ($30M Series B, 2024), Kin Insurance ($35M Series C, 2023)
• LinkedIn: Victor Gutwein LinkedIn
• Sector Focus: fintech, SaaS, marketplace, insurtech
• Stage Focus: pre-seed, seed, Series A
• Office Location: 130 East Randolph Street, Chicago
• Website: m25.vc

10. Chicago Ventures

Local fund backing Chicago infrastructure companies including payments and financial services platforms.

• Recent Deals: SpotHero ($50M Series D, 2023), G2 ($157M Series E, 2022), ActiveCampaign ($240M Series C, 2021)
• LinkedIn: Kevin Willer LinkedIn
• Sector Focus: B2B fintech, payments, marketplace, enterprise software
• Stage Focus: Series A, Series B, Series C
• Office Location: 350 North Orleans Street, Chicago
• Website: chicagoventures.com

11. Bain Capital Ventures

Boston-based fund with active Chicago office backing Midwest fintech infrastructure companies.

• Recent Deals: Amount ($99M Series D, 2024), Toast ($400M Series F, 2021), Flywire ($120M Series E, 2020)
• LinkedIn: Matt Harris LinkedIn
• Sector Focus: fintech, vertical SaaS, payments, banking infrastructure
• Stage Focus: Series A, Series B, Series C
• Office Location: 131 South Dearborn Street, Chicago
• Website: baincapitalventures.com

12. G2VP

Healthcare payments specialist with deep expertise in medical billing and claims processing.

• Recent Deals: Bright Health ($635M Series E, 2021), Livongo ($105M Series E, 2019), Quartet Health ($60M Series C, 2020)
• LinkedIn: Rick Klausner LinkedIn
• Sector Focus: healthcare fintech, medical billing, claims processing, digital health
• Stage Focus: Series A, Series B, Series C
• Office Location: 200 West Madison Street, Chicago
• Website: g2vp.com

13. Apex Venture Partners

Early-stage fund with insurance and financial services focus backed by former insurance executives.

• Recent Deals: Kin Insurance ($35M Series C, 2023), Corvus Insurance ($100M Series C, 2021), Ladder Life ($100M Series D, 2021)
• LinkedIn: Nancy Lurker LinkedIn
• Sector Focus: insurtech, B2B fintech, healthcare, consumer
• Stage Focus: seed, Series A, Series B
• Office Location: 325 North Wells Street, Chicago
• Website: apexventurepartners.com

14. Corazon Capital

Mexican-American founder backing fintech infrastructure for cross-border payments and remittances.

• Recent Deals: Nowports ($150M Series C, 2022), Clara ($70M Series B, 2021), Tribal ($60M Series A, 2022)
• LinkedIn: Alejo Czerwonko LinkedIn
• Sector Focus: cross-border fintech, B2B payments, logistics, remittances
• Stage Focus: seed, Series A, Series B
• Office Location: 110 North Wacker Drive, Chicago
• Website: corazoncapital.com

15. Cultivian Sandbox

Agtech investor backing supply chain finance and agricultural payments platforms.

• Recent Deals: Indigo Agriculture ($360M Series F, 2021), Farmers Business Network ($300M Series G, 2021), Taranis ($30M Series C, 2021)
• LinkedIn: Nicky Pardoe LinkedIn
• Sector Focus: agtech payments, supply chain finance, agricultural lending, food technology
• Stage Focus: Series A, Series B, Series C
• Office Location: 200 West Jackson Boulevard, Chicago
• Website: cultiviansbvc.com

16. Mucker Capital

West Coast seed fund with Chicago portfolio companies and active Midwest presence.

• Recent Deals: Honey ($4B acquisition, 2020), Blispay ($50M Series B, 2018), Public.com ($220M Series D, 2021)
• LinkedIn: Will Hsu LinkedIn
• Sector Focus: consumer fintech, payments, lending, insurtech
• Stage Focus: pre-seed, seed, Series A
• Office Location: Active in Chicago via portfolio
• Website: muckercapital.com

17. 500 Global

International accelerator and seed fund backing Chicago fintech startups through local programs.

• Recent Deals: Credit Karma ($500M exit, 2020), Talkdesk ($10B valuation, 2021), Canva ($40B valuation, 2021)
• LinkedIn: Dave McClure LinkedIn
• Sector Focus: fintech, SaaS, marketplace, consumer
• Stage Focus: pre-seed, seed, Series A
• Office Location: Programs at 1871, Chicago
• Website: 500.co

18. TechNexus

Corporate-backed venture fund connecting Chicago startups with enterprise financial services buyers.

• Recent Deals: Amount ($99M Series D, 2024), Vestwell ($125M Series D, 2024), Clearcover ($200M Series D, 2023)
• LinkedIn: Terry Howerton LinkedIn
• Sector Focus: enterprise fintech, banking infrastructure, insurtech, B2B payments
• Stage Focus: seed, Series A, Series B
• Office Location: 20 North Wacker Drive, Chicago
• Website: technexus.com

Start tracking your Chicago fintech investor outreach

These 18 investors closed Chicago fintech deals in 2025-2026. Before you start reaching out to Chicago funds, set up proper tracking.

Upload your deck to Ellty and create a unique link for each Chicago fintech investor. You'll see exactly which slides they view and how long they spend on your unit economics and regulatory approach. Chicago fintech investors typically skip the market size deck but focus heavily on your banking partnerships, compliance strategy, and path to profitability.

When Chicago investors ask for more materials, share an Ellty data room instead of messy email threads. Your financial model, banking agreements, regulatory analysis, and customer contracts in one secure place with view analytics.

Common questions

Do I need to be based in Chicago to raise from Chicago fintech investors?

No, but physical presence helps. Chicago fintech VCs prefer local companies because they can make enterprise introductions and provide hands-on support. Remote companies need stronger traction.

How does Chicago compare to SF or NYC for fintech fundraising?

Chicago has better B2B fintech expertise and enterprise connections. SF has more capital and higher valuations. NYC has larger check sizes for later-stage rounds. Chicago works best for banking infrastructure and insurtech.

What's the average seed round size in Chicago fintech?

$1-3M for pre-seed, $3-5M for seed, $8-15M for Series A. Chicago expects more revenue at each stage than coastal markets. You'll need $1-2M ARR minimum for Series A.

Should I raise locally or go straight to SF/NYC?

Raise locally if you're building B2B fintech or need enterprise customer access. Go coastal if you're doing consumer fintech, crypto, or need $20M+ Series A rounds. Most Chicago companies mix local and coastal investors by Series A.

Do Chicago fintech investors expect in-person meetings?

Yes, especially for first meetings and term sheet discussions. Chicago's fintech scene is relationship-driven. Plan to spend time in the city if you're serious about raising here.

What fintech sectors get funded most in Chicago?

B2B payments, insurtech, wealthtech, and banking infrastructure. Chicago investors understand regulatory complexity and enterprise sales cycles. Consumer fintech and crypto get funded at much lower rates.

How long does fintech fundraising take in Chicago?

3-6 months from first meeting to closed round. Chicago investors move slower than SF but faster than most East Coast markets. They're doing serious diligence on regulatory approach and banking partnerships.