Matchmakers in Chicago
Find professional matchmakers in Chicago, IL. Compare services and pricing.
8 matchmakers found
inluv
inluv is a matchmaking service for the Jewish community, founded by Talia Aloush, taking on both str...
Selective Search
Selective Search is a premium retained matchmaking firm for clients who value their time, privacy, a...
Eight At Eight Dinner Club
Rather than one-on-one introductions, Eight at Eight seats four single men and four single women tog...
Soul Search
Soul Search is a Chicago-based matchmaking service drawing on 20 years of experience from founder So...
Stef and the City
Chicago matchmaker Stef Safran runs Stef and the City, working with clients from their twenties thro...
Love And Matchmaking
Destin Pfaff and Rachel Federoff, both previously of Bravo's Millionaire Matchmaker, run Love And Ma...
Matchmaking For Men
Founder Louie Felix has worked in matchmaking for nearly 23 years and takes only male clients, sourc...
Connectricity
Trenia Norford founded Connectricity in Chicago in 2010, after a career that began in magazine publi...
Matchmaking in Chicago
Chicago is a more serious matchmaking market than its national profile suggests, and it is where one of the industry's most influential firms was built. Selective Search was founded here by Barbie Adler, a former executive recruiter who applied headhunting methodology to matchmaking — an approach that has since been widely imitated and that still shapes how this market operates.
The Chicago Market
Trading, law, medicine and consulting dominate the client base, with heavy Booth and Kellogg alumni representation. Demand concentrates in the Loop, River North, the Gold Coast and Lincoln Park, with a distinct and wealthy North Shore market in Evanston, Winnetka and Highland Park. Chicago clients are notably direct and price-conscious relative to the coasts.
What Matchmaking Costs in Chicago
Somewhat below New York and Los Angeles. National firms report local searches from around $30,000. Independent Chicago matchmakers commonly run $10,000–$35,000, and the mid-market is better served here than in most cities.
For a fuller breakdown of what matchmakers charge and why the numbers vary so much, see How much does a matchmaker cost?.
Last reviewed: August 2026. Figures are compiled from public reporting, vary considerably between sources, and are reported rather than confirmed. Check current pricing with each firm directly.
Who Uses Matchmakers in Chicago
Traders and quants, attorneys at the large firms, physicians and academic clinicians, consultants, and corporate executives. The winter months produce a pronounced seasonal pattern in inquiries.
What to Ask in Chicago
Ask how the firm sources outside its existing database. Chicago's professional circles are tightly connected, and a matchmaker drawing only on their existing pool may reintroduce you to people you already know professionally.
What to ask any matchmaker before you sign
- Where do your matches come from? A real answer describes a network and active recruiting. A vague one usually means a shared database you are being added to.
- How many clients do you take at once, and who actually runs my search — you, or an associate?
- What is the contract length, and what happens if I meet someone in month two?
- How many introductions am I guaranteed, in writing?
- Have you worked with someone in my situation before — my age, my background, my city?
Most firms in this category work on 12-month contracts paid in full upfront, so the answer to the third question is worth more than the price itself.
Firms Serving Chicago
Selective Search is headquartered in Chicago. Kelleher International also serves the market. The independent field here is strong and generally more affordable than coastal equivalents.
Most firms in this category work remotely and take clients across several cities, so a firm listed here may not have a local office. Ask where their matches actually live before you assume local coverage.
Matchmaking in Chicago
Who typically hires a matchmaker in Chicago?
Transplants, more often than not. People move to Chicago for work and find that a city with a genuine reputation for friendliness is still difficult to break into socially, because the established circles formed long before they arrived. The balance of the local pool also tends to favour women more than it does in the coastal markets, which is worth knowing before you assume your odds.
What should I ask a Chicago matchmaker before signing?
Ask how the firm sources outside its existing network, because that is the real constraint here. In a market where social circles are long established and hard to enter from outside, a database built from those same circles will keep showing you the same limited pool. Ask how many of their candidates arrived in Chicago recently, and how they reach people who are not already in their network.