Great Expectations Chicago

Great Expectations Chicago is a premiere, real world dating service enjoyed by fun-loving Chicago singles just like you. We know in today's chaotic world, quality singles are hard to find, which is why we take care of the basics and leave the biggest decisions to you. Our expert matchmakers provide personalized service right here at our Chicagoland offices in Schaumberg, giving you the attention and services to help you find the perfect match.

If you chose to make us your personal dating service, you will be guaranteed:



Great Expectations is Chicago’s most trusted safe dating service, with more than 30 years experience bringing together successful, professional singles. One reason for our long running success is because first and foremost, we value safety and privacy. Our screening process not only ensures that our membership consists of the most qualified and desirable of Chicago’s singles, it gives our members a safe and fun dating environment. You’ll feel more comfortable to be yourself and meet new people knowing... Read More →



No Chicago dating services have the track record for privacy and reliability offered by Great Expectations Chicago. We’ve been bringing happy couples together for more than 30 years, all while respecting your privacy by guarding the personal details that make you, you. Only with Great Expectations can you meet quality Chicago singles without exposing your identity to spammers, marketers, identity thieves and even potential online stalkers. That’s because Great Expectations offers personalized dating services... Read More →



With a Great Expectations Chicago membership, you’ll enjoy meeting real people with personality and real lives. So many of our members are busy professionals who look forward to escaping the demands of work to relax and meet new people socially for once. Great Expectations gives you the opportunity to be yourself, and meet other people without pretension or pressure! It’s dating at your speed, on your level, suited for your personality. Our matchmaking services are well suited for real people with authentic... Read More →


Serious Singles

Great Expectations Chicago is just as serious about dating as its members. All our members are quality Chicago singles who aim to find long-term companionship that works! We’re not in it for flings that flameout, because we’ve all been there and done that. We aspire for more, and so should you. You might say we have Great Expectations for your love life, just like you do. We take the expectations of our members seriously. But Great Expectations Chicago isn’t for everyone, and it shouldn’t be.... Read More →


Singles Events

Looking for the hottest Chicago singles events, but tired of all the fake trendy people who go to them? Great Expectations is your answer, hosting Chicago events for singles—but not just any singles—real people who are serious about dating. Great Expectations has some of the most popular, well-attended events for singles in Chicago. Our local singles events hosted by our matchmaking experts and professional event planners that cater to a wide range of singles throughout the Chicago metro. Our Chicago singles events... Read More →


Experienced Matchmaking

Great Expectations has a long track record as a Chicago matchmaking service, boasting more than 30 years of bringing Chicago singles together, with the goal of finding real companionship that lasts. Great Expectations is dating done right. We aim to produce quality relationships that last, and we have the intuition and expertise to pull it off. We realize there are a lot of newcomers offering new dating services, but none of them do it the Great Expectations way, with real-world services provided on-site at our Chicagoland... Read More →

The main focus that we center around is YOU! And with all that we have to offer, we hope that you will chose us. In return, you will receive our best upscale dating services.

We have more than 30 years experience bringing together happy couples. It's what we're known for, long before fads like online dating. Unlike other dating services, we value our member's privacy and safety. Great Expectations invests in its singles community by screening members for quality, starting with background and credit checks. Of course, we meet all our members personally to take note of their personal dating goals, and begin making the steps toward meeting professional Chicago singles!

As part of our matchmaking services you'll receive updated profile photography and a customized video personal ad introducing you to other members, and vise-versa. It's the most in-depth and accurate matchmaking method there is. In addition, you'll receive exclusive access to the hottest Great Expectations Chicago singles events, from pub-crawls and sporting events, to our annual singles luxury cruise.

If you're not using Great Expectations Chicago, you're looking for love in all the wrong places. It's time for something different. It's time to get serious. Take advantage of Great Expectation's exclusive dating services and start meeting the right people. Join today, and a Great Expectations matchmaker will get you on your way. Don't wait! You never know who you might be missing.

Who Are You Seeking?


Christian Singles

Great Expectations is the best opportunity that Chicago Christian singles have for finding Godly companionship in Illinois. Our value-based community of Christian singles is a... [Read more]


Single Parents

As a single parent, finding the time to date can be a seemingly impossible task. Meeting new people (and quality people at that) is a rare happening, but all that can change with... [Read more]


Divorced Singles

If you’re a Chicago divorced single that is ready for a new start, you are in the right place! Great Expectations is an experienced dating service with a program that is... [Read more]


Fitness Singles

Want to meet Chicago singles that value their bodies and have made fitness a priority? You can meet them through Great Expectations – the most reliable dating service in Illinois.... [Read more]


Mature Singles

Meet professional and mature singles in our community at Great Expectations Chicago. Our personable matchmakers have been arranging dates and joining couples for more than thirty... [Read more]

Your Target Age Range


20 Something Singles

If you are a 20 something single in Chicago, and even the slightest bit curious about professional dating services, it’s probably because you have seen through the illusion... [Read more]


30 Something Singles

It’s a good time to be over thirty and single in Chicago! Great Expectations has been playing matchmaker for Chicago 30 something singles for over 30 years. And while we... [Read more]


Over 40 Singles

Experience has been our key to success as matchmakers in Chicago, and as a 40 something single, we think you’ll agree that experience is everything. You’ve come a... [Read more]


Singles Over 50

If you’re single and over 50, then you’re in the right place. Great Expectations Chicago has more than thirty years of experience playing cupid for members who are... [Read more]


Senior Singles

If you’re a Chicago senior and looking for reliable companionship, Great Expectations can help. Our team of experienced matchmakers has an impressive reputation for successfully... [Read more]