5 Best Millionaire Matchmakers For Chicago Singles

The 5 best millionaire matchmakers in Chicago range from $1,595/month (VIDA Select) to $1,000,000+ (Selective Search). Top options include VIDA Select for flexible monthly packages and 82% success rates, Enamour for accomplished professionals ($20,000+), and Kelleher International for comprehensive search packages ($30,000-$300,000+). Most elite services require 1-3 year contracts with substantial upfront investments, though VIDA Select offers packages with month-to-month flexibility.

Report Methodology: The Weighted Review Score combines ratings from Trustpilot, Yelp, and Google, weighted by the number of reviews on each platform. To ensure reliability, services with fewer than 10 total reviews receive a confidence adjustment: 10+ reviews (full weight), 5-9 reviews (90% weight), 2-4 reviews (80% weight), and single reviews (70% weight). For instance, if a service only has a single 5-star review, their weighted score would be 3.5 stars. This prevents services from ranking artificially high based on limited feedback and provides a more accurate comparison based on client experiences. Last Updated: 12/10/2025

Key Insights:

• Some services offer specific match guarantees while others focus on unlimited introductions over contract periods
• Mid-range executive matchmaking services range $20,000-$45,000 annually, with options like Enamour's invite-only database ($20,000) and Kelleher International's local search packages ($30,000+)
• Premium millionaire matchmaking reaches $150,000-$1M+ for ultra-high-net-worth singles, including Selective Search's concierge services and Patti Stanger's direct access packages starting at $285,000. 
• Chicago's top matchmakers offer specialized services beyond introductions, including image consulting, professional photography, relationship coaching, and exclusive mixer events for busy executives.

Our team has reviewed over 200 matchmaking services, diving deep into their processes, matchmaking approaches, success rates, and client experiences. We've been in the industry since 2009, and all our reviews are built on extensive research plus a keen understanding of the matchmaking landscape.

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Enamour

For over ten years, Enamour's elite matchmakers have assisted accomplished and selective individuals in finding perfect matches through psychology-based compatibility assessment.

Clientele: Accomplished professionals seeking white-glove matchmaking experience

Process: Each client receives a dedicated matchmaker who learns personality and preferences. The team emphasizes relationship psychology during vetting, using this knowledge to select truly compatible matches from their exclusive, invite-only database. Matchmakers combine AI and recruiting technology to scout highly compatible singles beyond their internal pool.

Cost: Matchmaking packages start at $20,000, tailored to each client's specific search requirements

What Sets Them Apart: Psychology-focused approach combined with technology and extensive post-date feedback systems for search refinement

VIDA Select

VIDA Select's modern matchmaking approach provides access to an unparalleled pool of eligible Chicago singles with total client control over match selection through pre-approved dating.

Clientele: Successful professionals seeking efficient, results-driven matchmaking

Process: Clients pre-approve all dates by selecting from meticulously curated match lists. The process begins with complimentary consultation, followed by dedicated matchmaker assignment and active search management.

Cost: Monthly packages start at $1,595 with no long-term commitment. Results-guaranteed package provides 5+ curated matches within 90 days for $5,750—guaranteed results or continued work at no extra cost.

What Sets Them Apart: 82% success rate with most clients meeting someone special in 3 months, month-to-month flexibility without contracts, and complete match pre-approval control

Kelleher International

This exclusive San Francisco-based service operates through mother/daughter team Jill Kelleher and Amber Kelleher-Andrews, with established Chicago presence serving high-net-worth professionals.

Clientele: Affluent professionals seeking comprehensive search options from local to international scope

Membership Packages:

• Local Search: Chicago area matches starting at $30,000 (additional cities $5,000 each)
• National Search: Starting at $45,000
• CEO Club: $150,000-$300,000+ including international search and founder consultation

Contract Terms: 1-3 year memberships including one year of "hold" time for travel or relationship exploration

What Sets Them Apart: Flexible geographic scope options, extensive hold time policies, and founder-level consultation availability

Millionaire’s Club

Patti Stanger's "Millionaire Matchmaker" service operates from Los Angeles with affiliated Chicago matchmakers, offering comprehensive lifestyle services beyond matchmaking.

Clientele: Ultra-high-net-worth individuals seeking celebrity matchmaker expertise

Service Options:

• Team Matchmaking: $45,000-$100,000+
• Direct Patti Stanger Access: Starting at $285,000
• Mixer Experiences: $20,000-$35,000 for curated events with 10-25 handpicked singles
• Deluxe Mixer: $30,000 with Patti Stanger personally hosting and introducing up to 20 singles

Additional Services: Image consulting, date coaching, relationship counseling, and professional photography

What Sets Them Apart: Celebrity matchmaker brand recognition, comprehensive lifestyle services, and unique mixer event options

Further Reading: Millionaire's Club review

Selective Search

Chicago-based executive matchmaking service founded by former corporate headhunter Barbie Adler in 2000, applying recruitment strategies to relationship matching.

Clientele: Executive-level professionals seeking comprehensive concierge matchmaking

Process: Begins with 2-hour interview covering background, relationship goals, and ideal partner criteria. Search includes finite number of introductions over set time periods with detailed contract specifications.

Cost: $25,000-$250,000+ for year-long contracts, potentially reaching $1,000,000+ for elevated concierge elements

Contract Flexibility: Membership pause available in 30-day increments, but freeze time must be negotiated upfront in contract

What Sets Them Apart: Corporate recruitment methodology, Chicago headquarters with national network, and highly customizable concierge services

Further Reading: Selective Search review