
Dating in Chicago can be exciting, sophisticated, and frustrating all at the same time. The city offers incredible restaurants, rooftop lounges, lakefront walks, cultural events, and some of the most successful professionals in the country. Yet many Chicago singles tell us the same thing: they are busy, overwhelmed by dating apps, and tired of wasting time on people who are not looking for a serious relationship.
At Cinqe Matchmaking, we work with successful men and women throughout Chicago and the surrounding suburbs who are seeking a meaningful relationship, marriage, or a long-term partner. Whether you live in Gold Coast, Lincoln Park, River North, West Loop, Streeterville, Lakeview, Wicker Park, Old Town, Hinsdale, Naperville, Winnetka, Highland Park, Lake Forest, or Oak Brook, our team can help.
Our clients are executives, business owners, entrepreneurs, physicians, investors, attorneys, and accomplished professionals who value privacy and prefer a more personalized approach than dating apps.
Cinqe has been featured in Business Insider, Maxim, Elle Magazine, HuffPost, NBC, ABC, Fox, The Chronicle, Yahoo News, and many other publications. We have also been recognized with multiple industry awards for luxury matchmaking services.
Cinqe has been helping singles find meaningful relationships since 2010.
Our team has been featured by major media outlets and recognized throughout the luxury matchmaking industry. We are known for our hands-on approach, extensive network, and ability to connect successful singles across the United States and internationally.
Many of our Chicago members appreciate that they are not limited to one city. Through our network, they gain access to introductions they would likely never encounter on their own.
Whether you are seeking someone in Chicago, Florida, California, Texas, New York, Europe, Australia, or beyond, our team can assist.


Chicago has one of the largest dating pools in America, yet many singles struggle to find the right match.
The city is often described as a collection of neighborhoods. Someone living in Lincoln Park may rarely date someone in Hyde Park. A professional in River North may not want to commute to the North Shore for every date. Add demanding careers, long winters, travel schedules, and dating app fatigue, and many successful singles find themselves stuck.
Common challenges we hear from Chicago singles include:
Our role is to remove much of that frustration and introduce you to carefully selected matches.
Unlike dating apps, we do not rely on algorithms.
Every client works with a professional matchmaker who learns about their lifestyle, goals, personality, values, and relationship preferences. We then search locally throughout Chicago and nationally through our network of accomplished singles.
Many of our Chicago clients are open to dating beyond Illinois. We frequently facilitate introductions between members in:
Some clients prefer to meet someone locally, while others are open to relocating or building a relationship across multiple cities.


Many of our members are highly visible professionals who cannot comfortably use dating apps.
We regularly work with:
Our process is discreet, confidential, and designed to protect your privacy while expanding your dating opportunities.
Every introduction is handled personally by our team.
Our premium clients work directly with a matchmaker who conducts a personalized search and arranges introductions on their behalf.
Membership fees for Chicago searches typically begin at $25,000.
Many singles choose to join our private database at no cost.
When a client hires us and your profile matches their search criteria, we may contact you regarding an introduction.

For those seeking guaranteed dates and the opportunity to work one-on-one with a matchmaker, see the details below.
Email us at love@cinqe.com and we’ll follow up with a brief phone call to learn about your dating goals, ideal match, and answer initial questions.
love@cinqe.comYou’ll connect with our Chicago team by phone and video for a deeper conversation about compatibility, process, and next steps. After this meeting, we’ll send a personalized offer.
Once you sign, your matchmaker gets to work and you can begin meeting your curated matches.
Chicago Matchmaking
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