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

Still single in the Windy City? The dating scene can be tough, but working with a Chicago matchmaker can dramatically boost your odds of meeting your perfect match. They do all the hard work for you!

A couple enjoying a coffee date in Chicago

But deciding which one to invest in may seem like a daunting task.

Don’t worry - we did the research for you.

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 website

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.


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


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.

VIDA Select (by Scott Valdez)

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.


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


VIDA's matchmaking package prices highly reflect the number of hours that should be devoted to finding you highly compatible singles each month, taking into account your "ideal match" criteria, number of locations, etc. Clients choose from 3 levels of service: Basic, Premium and Elite.

Basic packages start at $1195 a month, Premium packages start at just $1795 a month and Elite options begin at $2595 a month. On average, it only takes clients 3 months to meet someone special.

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 a 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!

Selective Search  matchmaking website

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.


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


The Basic membership package starts at $25,000, and includes up to 10 matches in one city over the course of a year.

The Elite membership package starts at $50,000, and includes up to 10 matches in 5 different cities around the country.

If you’re under 35, you can opt for the Young Executive membership. That starts at $15,000 and includes up to 6 matches over a 6- or 12-month period.

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.

Further Reading

Selective Search review

Ambiance Matchmaking (by Leslie Wardman)

Leslie Wardman from Ambiance Matchmaking

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


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


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.

Further Reading

Ambiance Matchmaking reviews

Three Day Rule (by Talia Goldstein)

three day rule reviews

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.


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


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.

Further Reading

Three Day Rule reviews

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

Matchmakers Jill and Amber Kelleher

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.


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


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.

Further Reading

Selective Search vs Kelleher International review

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Why Choose VIDA Select?

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Since 2009, thousands of clients have discovered true love thanks to VIDA Select’s fresh, modern approach to matchmaking – which has finally thrown blind dates and long-term contracts out the window. This isn't your grandmother’s matchmaking!

Instead of working with a single matchmaker using a small rolodex of potential partners, VIDA Select’s matchmaking team taps into the world’s largest database of available singles. We’ll quickly identify the matches who check all of your boxes so you can finally experience true chemistry. Are you ready to become our next success story? Schedule your complimentary consultation now by clicking the button below!

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