Your anxiety, jealousy, and anger aren't broken — they're ancient software running in a world they weren't built for. This book is the missing manual.

“The most eye-opening book on emotions I've ever read.”

Get It on Amazon →Available in paperback & Kindle

Best Matchmakers in Chicago

Expert rankings of the top matchmakers in Chicago, scored on safety, ease of use, value, and match quality.

Chicago is home to Selective Search, one of America's most respected matchmaking firms with a database of over 250,000 singles. The Midwest's largest city has a thriving professional matchmaking scene that caters to executives and young professionals alike. Chicago's reputation for genuine, down-to-earth relationships makes it a strong market for serious matchmaking.

Top Matchmakers (12)

💎

Kelleher International

✓Luxury Matchmaking

Affluent professionals seeking long-term commitment

9.5

From $2,500/mo

🔍

Selective Search

✓Luxury Matchmaking

Executives and professionals seeking marriage-minded partners through personalized, offline matchmaking

9.2

From $2,083/mo

💘

Tawkify

✓Executive Matchmaking

Busy professionals who want curated matches without app fatigue

9.0

From $833/mo

📅

Three Day Rule

✓Executive Matchmaking

Young professionals in major US cities

8.9

From $833/mo

🎯

VIDA Select

✓International Matchmaking

Professionals who want a modern, data-driven matchmaking approach

8.7

From $995/mo

🏆

The League

✓Tech-Assisted Matchmaking

Ambitious professionals who want a vetted dating pool

8.1

Free

🍽️

It's Just Lunch

✓Executive Matchmaking

Busy professionals who want low-pressure first dates

8.0

From $417/mo

🌹

Hinge

UnverifiedTech-Assisted Matchmaking

Millennials and Gen Z singles looking for serious relationships through engaging profile prompts

8.0

Free

🐝

Bumble

UnverifiedTech-Assisted Matchmaking

Women who want to control the conversation and singles seeking a respectful dating environment

8.0

Free

💕

eHarmony

UnverifiedTech-Assisted Matchmaking

Relationship-minded singles looking for long-term commitment through scientific matching

7.8

Free

❤️

Match.com

UnverifiedTech-Assisted Matchmaking

Singles of all ages looking for both casual and serious relationships on a well-established platform

7.5

Free

☕

Coffee Meets Bagel

UnverifiedTech-Assisted Matchmaking

Busy professionals who prefer quality over quantity with a limited daily match format

7.5

Free

The Management Companion

Happy Employees

What Evolution Tells You About Leading People

Lead with human nature, and your team won’t just perform — they’ll thrive.

Get It on Amazon →Paperback & Kindle

How Much Does a Matchmaker Cost in Chicago?

Matchmaking services in Chicago typically range from $1,000 - $25,000+ depending on the level of service.

Service	Category	Monthly Cost
Kelleher International	Luxury Matchmaking	USD 2,500/mo
Selective Search	Luxury Matchmaking	USD 2,083/mo
Tawkify	Executive Matchmaking	USD 833/mo
Three Day Rule	Executive Matchmaking	USD 833/mo
VIDA Select	International Matchmaking	USD 995/mo
The League	Tech-Assisted Matchmaking	Free tierUSD 33.33/mo
It's Just Lunch	Executive Matchmaking	USD 417/mo
Hinge	Tech-Assisted Matchmaking	Free tierUSD 29.99/mo
Bumble	Tech-Assisted Matchmaking	Free tierUSD 29.99/mo
eHarmony	Tech-Assisted Matchmaking	Free tierUSD 35.9/mo

Frequently Asked Questions

What is the best matchmaker in Chicago?

Selective Search is Chicago's flagship matchmaking firm with one of the largest databases in the industry. Tawkify and Three Day Rule also have strong Chicago operations for mid-range budgets.

How much does matchmaking cost in Chicago?

Chicago matchmaking ranges from $5,000 for services like Tawkify to $25,000+ for Selective Search's premium packages. It's Just Lunch offers more accessible options starting around $2,500.

Is Chicago a good city for matchmaking?

Yes, Chicago's large professional population, Midwest values, and concentration of matchmaking services make it one of the best US cities for finding a serious partner through a matchmaker.

Do Chicago matchmakers serve the suburbs?

Most Chicago-based matchmakers serve the entire metropolitan area, including suburbs like Naperville, Evanston, and Oak Park. Selective Search and Tawkify have particularly strong suburban networks.

How does Selective Search work in Chicago?

Selective Search conducts in-depth personal interviews, uses a network of scouts to recruit quality singles, and draws from their 250,000+ person database. Their Chicago headquarters gives local clients direct access to the core team.