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Top 5 Millionaire Matchmakers In Chicago [Which One Is Best For You?]

Since you’re looking for the best millionaire matchmakers in Chicago, you’ve already realized hiring a matchmaking service is one of the best ways for busy professionals like you to meet high-quality, intriguing singles.

Start your search here, with these 5 Chicago millionaire matchmakers!


Enamour Chicago

For more than ten years, Enamour's team of elite matchmakers has been assisting accomplished and selective individuals in finding their perfect matches.

Enamour's matchmaking process begins by pairing each client with a dedicated matchmaker, who takes the time to learn about their personality and preferences. Enamour's team places a strong emphasis on relationship psychology during the vetting process, using this knowledge to carefully select potential matches that are truly compatible with their clients.

Matches come from Enamour's exclusive, invite-only database. Matchmakers also use a combination of AI and recruiting technology to scout for highly compatible singles. After each date, clients have the opportunity to provide and receive feedback to help their matchmaker refine their search and find the perfect match.

Matchmaking packages start at $15,000, with each one tailored to a client's specific search.

VIDA Select

VIDA Select Chicago millionaire matchmaker website

Thanks to taking a modern approach to matchmaking, VIDA Select's matchmakers have access to an unparalleled pool of eligible Chicago singles. And you have total control over who you want to meet! By selecting potential matches from a meticulously curated list, you get to pre-approve all your dates.

And unlike many other elite matchmaking services, VIDA Select doesn't require a long-term contract. With a payment structured designed for client convenience, you simply pay for every month you'd like an active search conducted on your behalf. You can pause your service as often as you need, and for any reason.

Why pay for an entire year’s worth of service if you might meet your ideal partner the very first month?

VIDA offers various packages, with Basic matchmaking services starting at $995 per month. Premium packages begin at just $1595, while Elite options start at only $2395 per month.

The cost of your matchmaking package is primarily determined by the amount of time required to find highly compatible matches for you each month, taking into account factors such as your match criteria and the number of locations you are considering.

The matchmaking process begins with a complimentary consultation to learn more about how the service works.

Kelleher International

Millionaire matchmakers Jill and Amber Kelleher

Helmed by mother/daughter matchmaking team Jill Kelleher and Amber Kelleher-Andrews, this exclusive matchmaking service is based in San Francisco and has a branch in Chicago.

Kelleher International offers 3 membership packages, which typically last 1 to 3 years. They vary based on the scope of the search you want:

CEO Club:
$150,000 to $300,000+
Includes an international search for matches
Personal consultation with one of the founders
National Search:
Starts at $45,000
Local Search:
Meet matches in the Chicago area
Starts at $30,000
Option to add additional cities for $5,000/each

All of the membership levels include a year’s worth of “hold” time. That means you can put your search on hold as needed while you travel or if you just want to see where things go with a promising match.

The number of matches you’re guaranteed varies from client to client, as it depends on factors like your location and how specific your “ideal partner” criteria is.

To get started with Kelleher International, prospective clients can either call this millionaire matchmaking service directly, or fill out a short online form to request a phone call.

Next is an interview. It's either in-person or via Skype, and all the details of your membership package will be discussed in depth. Once you’ve signed the contract, your search will begin.

Millionaire’s Club

Millionaire's Club website

No list of millionaire matchmakers would be complete without mentioning Patti Stanger, famously known as “The Millionaire Matchmaker” thanks to her TV show.

Her upscale dating service, Millionaire’s Club, is based in Los Angeles but has affiliated matchmakers serving the Chicago area.

Stanger’s team offers more than just matchmaking. You’ll also find services like image consulting, date coaching, relationship and business counseling, and professional photography.

Matchmaking packages cost from $45,000 to over $100,000 to work with Stanger's team. Want direct access to Patti Stanger? Prices start at $285,000.

If you’re not interested in a membership, but still want to meet high quality, handpicked matches you can purchase a “Millionaire Matchmaker Mixer Experience.”

For $35K, Stanger will coordinate and host a party in your city, complete with 25 singles she chooses for you to meet.

Mixer Experiences are also available to paying clients. You can simply add one on to your membership package.

Prices start at $20k for a 3-hour dinner where you’ll meet up to 10 handpicked singles. Your matchmaker will be on hand to introduce you to them one by one.

If you want Stanger present at your party, opt for the $30k “Deluxe Mixer.” She’ll personally introduce you to up to 20 singles at an event held at an “upscale” venue.

One thing to consider. With the exception of the Deluxe Mixer, the cost of food, adult beverages, and rent for the venue are not included in the price, so you’ll be picking up the tab for those as well.

Selective Search website

Selective Search is a Chicago-based executive matchmaking service. Barbie Adler started it in 2000, after leaving the world of corporate headhunting. She now works with matchmakers all over the US.

Matchmaking packages range from $25,000 to $250,000+, with a year-long contract required for the search. Depending on the scope and complexity of your search, plus any "elevated concierge elements," the final price tag could top $1,000,000.

Your package will include a finite number of introductions over a set period of time, all of which will be detailed in your contract.

You have the ability to pause your membership in 30-day increments, but there’s one caveat. The amount of “freeze” must be negotiated up front into your contract. That means you’ll need to guess how much you may require within the next 12 months.

Working with Barbie Adler’s elite matchmakers starts with a 2-hour interview, during which you’ll cover the basics like your background, relationship goals, and “ideal partner” criteria. Once you hammer out all the contract details, your search begins.

Want to learn more about this exclusive Chicago dating agency? Check out this Selective Search 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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