Who's The Best Chicago Matchmaker For You? [6 Great Options!]

The 6 best Chicago matchmakers range from $1,595/month (VIDA Select) to $500,000+ (Selective Search). Top options include VIDA Select for flexibility and access to quality matches, Enamour for professionals ($20,000+), and Three Day Rule for comprehensive service ($5,900+). Most require 6-12 month contracts with varying match guarantees and international reach.

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: 11/03/2025

Key Insights:

• Budget-friendly: VIDA Select (starting at $1,595-$2,595/month, no long-term contract), Three Day Rule ($5,900+)
• Mid-range: Enamour ($20,000+), Ambiance Matchmaking ($25,000-$100,000+)
• Premium: Selective Search ($25,000-$500,000), Kelleher International ($30,000-$150,000+)
• Strong reviews: VIDA Select (4.5 stars), Three Day Rule (4.2 stars), Enamour (4.0 stars)
• Contract flexibility: Only VIDA Select offers month-to-month options

Our team of matchmaking experts created this guide to help Chicago singles find the best matchmaker. Our industry experience dates back to 2009, so we're well acquainted with all the players, from the boutique operations to the international services.

We’ve written over 200 matchmaker reviews, leveraging our in-depth knowledge of the landscape and our deep understanding of what clients value most.

From cost to what to expect, see which of these 6 best Chicago matchmakers is right for you!

Enamour

With its exclusive, invite-only database and focus on relationship psychology, Enamour is perfect for accomplished, selective Chicago singles who want to meet high-quality matches.

Clientele

Enamour offers a tailored experience to men and women looking for a luxury matchmaker.

Cost

Matchmaking packages begin around $20,000.

What To Expect From Enamour

A white glove service from start to finish, the process begins when you're paired with your dedicated personal matchmaker. She'll gather all the details she needs about your lifestyle, goals and ambitions, matching criteria, etc., then hand-select compatible matches from Enamour's database of Chicago singles.

But the search for your ideal partner extends far beyond that. Enamour uses both recruiting technology and an extensive network of scouts to pinpoint compatible singles. Every potential match then undergoes a thorough screening process that takes place in person or via video.

After each introduction, your matchmaker will touch base with both you and your match. This feedback process allows for the search to be fine-tuned, and you'll also gain valuable insights into your dating journey.

Enamour offers a host of complementary services such as dating/relationship coaching, image consulting, personal styling, and professional photography.

What People Are Saying About Enamour 

Enamour has a 4.0 star rating on Trustpilot with favorable reviews mentioning thoughtful matchmakers, candid feedback, and exceptional first dates.  

 

VIDA Select (by Scott Valdez)

Founded in 2009, VIDA Select puts a modern spin on traditional matchmaking by combining affordable prices with the flexibility to pay by the month.

Clientele

Both men and women, usually in their mid 20s to 60s.

Cost

Basic packages start at $1595 a month, with no long-term contracts required. There is also a $5750 "guaranteed results" package that gives you a minimum of 5 matches within 90 days, or the search continues at no extra cost. VIDA Select has an 82% success rate, with most clients meeting someone special within 3 months.

What To Expect From VIDA Select

VIDA is a 100% done-for-you matchmaking service, from generating interest in you to scheduling your dates with high-quality Chicago area singles.

Prospective clients start with a quick screening process to ensure they're a good fit with VIDA (and vice versa).

You'll then have an in-depth interview with your matchmaker. She'll get to know all about you and your idea of an 'ideal match.' All of VIDA's packages include unlimited matches, and you can approve or pass on each one based on their full profile.

VIDA also offers an array of services ranging from dating coaching to personal styling.

Learn more about VIDA’s services and schedule a 100% free, confidential consultation with one of our elite matchmakers!

What People Are Saying About VIDA Select 

You’ll find that VIDA has mostly positive reviews on Trustpilot. The matchmaking company has a 4.5-star rating, with several of the 5-star reviews sharing how much they liked their matchmaker, like these:   

 

Selective Search (by Barbie Adler)

A former Fortune 500 executive recruiter, Barbie Adler is a well-known matchmaker in Chicago.

She and her team of 20 only work with 500(ish) clients at any given time. Located at 35 East Wacker Drive, Adler also works with affiliated matchmakers around the US. The service was founded in 2000.

Clientele

The majority of Selective Search clients are men, but they also take women as paying clients.

Cost

The "introductory" membership packages start at $25,000, but that's only for potential clients who meet certain criteria. For most clients, basic packages begin around $50,000 and can range up to $500,000.

Packages generally include up to 10 matches over the course of a year. Depending on your level of service, you can include additional cities in your search.

What To Expect From Selective Search

Potential clients participate in a 2-hour interview. You'll discuss your ideal partner, relationship goals, personal background and more.

You’ll then get an unlimited number of profiles of singles your matchmaker feels are compatible. If the matches you select are also interested in meeting you, you’ll receive their contact information.

What People Are Saying About Selective Search

On Yelp, Selective Search has mixed reviews, resulting in a 3.1-star rating.  Those who gave the service 5 stars mentioned a positive experience with their matchmaker, like these:  

Further Reading

Selective Search review

 

Ambiance Matchmaking (by Leslie Wardman)

Although Ambiance Matchmaking was founded in Tulsa, Oklahoma, in 2002, they have a strong presence in Chicago.

Clientele

Predominantly men and women ages 36-49, with some clients in their 20s and 50s.

Cost

There are 4 membership levels to choose from: Local, National, International, and VIP. Prices start around $25,000 and can range over $100,000.

What To Expect From Ambiance Matchmaking

“Exclusive Members” work directly with Leslie Wardman, and she only takes on 20 clients at a time for this elite matchmaking service. You’ll receive 12-24 matches in 12 months, and 12 months of “hold” time.

Potential matches are identified from the Ambiance database of 10,000+ high-quality singles.

Each one is then further screened and interviewed to make sure they fit what a client is seeking, and vice versa. When a match is deemed compatible, first date arrangements are made.

This is a true millionaire matchmaker service – most of her VIP clients are top execs who generate at least $1 million in annual revenue.

National and Local members can choose from 6- or 12-month contracts, and receive a match at least once a month.

What People Are Saying About Ambiance Matchmaking

On Yelp, Ambiance Matchmaking has a 4-star rating based on less than a handful of reviews. The 3 5-star reviews discussed how they were glad they decided to work with Ambiance:   

Further Reading

Ambiance Matchmaking reviews

 

Three Day Rule (by Talia Goldstein)

Three Day Rule has a presence in several US cities, with Chicago being one of them. Founded by matchmaker Talia Goldstein in 2010, this service is based on the West Coast.

Clientele

Typically single professionals in their 20s to 60s who are seeking a long term relationship.

Cost

Matchmaking packages start at $5,900, which includes a 3-month membership and at least 3 matches. A 6-month contract starts at $9,500, and there is also a VIP membership that starts at $19,500.

Having a profile included in their eligible singles database is free. However you don't work directly with a professional matchmaker - you are only contacted if you fit what a paying client is looking for. You may never receive a single match that way.

What To Expect

If you hire Three Day Rule as your Chicago matchmakers, you'll be matched with other paying clients or with singles in their database.

When a potential match is found, you'll review a profile that includes photos. If you're interested in meeting, contact info is exchanged and you'll need to reach out to schedule the first date.

Because every match is carefully selected for your consideration, each presentation counts toward your guaranteed total, even if you decline to pursue the match.

What People Are Saying About Three Day Rule

Three Day Rule has a 4.2 rating on Yelp. This person shared that their matchmaker pushed them outside of their comfort zone: 

And this individual mentioned that working with the service gave her more confidence:

Further Reading

Three Day Rule reviews

 

Kelleher International (by Jill Kelleher & Amber Kelleher-Andrews)

Their elite matchmaking service is headquartered on the West coast. But Kelleher International is also one of Chicago’s most popular millionaire matchmakers. Jill Kelleher established this elite matchmaking service in 1986.

Clientele

Men and women who want to get married (or be in a serious relationship).

Cost

Membership prices are set according to the type of search you want. Local searches start at $30,000, national searches at $45,000, and an international search (the “CEO Club”) starts at $150,000.

What To Expect From Kelleher International

Memberships come with 13 months of “active” search time, plus 12 months “pause” time.

The exact number of introductions varies per client, and will be specified in your contract. It’s typically between 8 and 13 matches.

If you opt for the CEO level, you’ll get one-on-one consultations with Amber Kelleher-Andrews. Your personal matchmaker will only have 9 other clients.

What People Are Saying About Kelleher international

Kelleher International has a minimal online review presence. Combining their Yelp and Better Business Bureau profiles, fewer than 10 reviews exist in total, with the primary complaint from reviewers being issues related to their pricing structure.

Further Reading

Selective Search vs Kelleher International review