Fireworks Sale!
Get four free matches until the 19th!

Find Your Professional Matchmaker in Chicago

Tawkify is the smart choice for singles who are ready to stop searching and start building a real relationship.

Thousands of relationship ready singles in Chicago

Largest network of relationship-ready singles

4.6 stars on Trustpilot

Rated “Excellent” by thousands of Tawkify members

80%+ success rate*

6.5X more effective than dating apps. Dates are 100% guaranteed

*Tawkify relationship success rate for matched couples in first 8–12 matches with Tawkify. Dating app success rate based on Global Love Report by the Pew Research Center.

“Tawkify has matched people with some impressive status, like the lingerie designer and burlesque connoisseur Dita Von Teese.”

“If you wish someone else would do all the hard work for you, Tawkify may be your ideal dating companion.”

“You step into a service like nothing you’ve ever peeped at. And service is the right word — never, on any other dating site, will you ever feel more catered to.”

Chicago is a city of abundance. We have a skyline, a Great Lake, a signature hot dog. We have the Cubs. The University of Chicago. Malort. If you need it, chances are you’ll find it in Chicago—and that includes matchmakers.

We’re happy to report that Tawkify is firmly rooted in the Windy City. From Wicker Park to Navy Pier, our team of professional matchmakers know the lay of the land and the quirks of Chicagoland. Our personalized approach to matchmaking means that you’ll be set up with a variety of high-quality singles, all of whom are hand-picked based on your interests and preferences.

When you work with Tawkify, say goodbye to awkward first days and say hello to finding love.

Get Started toward Your Last First Date

Try Tawkify today. We only accept candidates we believe we can match.

Whether you’re new to the city or a Chicago native, you’ll be sure to benefit from working with a Tawkify matchmaker. Not only do they understand the specific challenges of dating in your city, they have the finger on the pulse of dating trends. Instead of worrying about crafting your perfect dating profile or dressing up for another night on the town, you get to spend your time doing the things that bring you joy while your dedicated Tawkify matchmaker does the hard work for you.

Our team of professional matchmakers takes a personalized approach to crafting meaningful connections. Through careful research and one-on-one consultations, they’re able to access their database of Chicago singles and find your potential partner.

If you live in Chicago and are impatient for that next stage in your life, let Tawkify take over.

Chicago is a great city: vibrant, cultured, and beautiful, with a population to reflect that. It’s also huge. Consistently ranked as the third largest city in the US, Chicago is filled to the brim with single folks. Unfortunately, that abundance isn’t necessarily a good thing—with so many choices, you’re more likely to end up with analysis paralysis than a perfect match.

Between all of the options and many Chicagoans’ busy schedules, people are hesitant to commit to a partnership, let alone a third date. To make things worse, a lot of people here don’t own a car—and who wants to take the El five stops across town for a date? You may as well be in a long-distance relationship with that cute European you met on vacation last year.

The good news is that dating in Chicago doesn’t need to be so hard. When you sign up with Tawkify, you get to make like a deep-dish pizza and rise to the top.

Anyone who’s seen The Fugitive knows that it’s easy to get lost in the Chicago crowds. Chicago’s big population means that at any given time, there’s a huge pool of single folks looking for love. It should be easy to jump on the apps and find your perfect match, right? Wrong…or you wouldn’t be reading this right now.

Matchmakers might not be the most common method of finding a partner in 2024, and we think that’s a good thing. The glut of everyone and their mother (sometimes, literally) joining dating apps means that you’re stuck swiping through hundreds of bad profiles just to find one potential date.

When you sign up with Tawkfiy, you get to skip the line at Disneyland. You go straight to the good stuff: in this case, Tawkfiy’s vast network of Chicago singles and a dedicated matchmaker who can help you find The One. Through one-on-one consultations and professional expertise, your matchmaker will help you find your perfect fit. You’ll be taking selfies in front of The Bean before you know it.

While Chicago may be located in the humble midwest, the cost of life here rivals any coastal city. The average price for a night out on the town is almost $100 here. If you add up all the evenings you’ve spent hitting the bars hoping to find someone, you’d probably have enough for a down payment on the condo of your dreams.

Matchmaking services in Chicago are similarly expensive, with some starting upwards of five figures. Luckily for you, Tawkify is the affordable matchmaking service. When you sign up with Tawkify, you get all the perks of working with a dedicated, experienced matchmaker without any of the sticker shock. To make things better, you also have access to additional, customizable services such as certified relationship coaching.

Don’t be duped into draining your bank account on a celebrity matchmaker. Work with Tawkify, and make an investment in your love life.

After New York City, Chicago is the US city with the highest population of Indians. There’s no shortage of East Asians in the Windy City—so why is it so hard to find a match?

If you’re single, Indian, and living in Chicago, you’re not alone. At Tawkify, we understand that cultural fit matters. Many of our Indian clients not only want to find someone to build a family with; they want someone who will fit into their existing family. Our dedicated matchmakers can help you find your perfect partner without sacrificing your passions, interests, and values. We give special consideration to your heritage and culture without falling back on stereotypes.

Chicago is a great city for Black singles…sort of. While there’s no shortage of African-American people in Chitown, there’s also a unique set of challenges for Black folks looking for love. Recent studies have shown that people of color face discrimination on dating apps, with Black people in particular suffering from racial bias. Thankfully, there’s a way around that nonsense.

Tawkify is a way to expand your network of Black singles and point yourself in the direction of lasting love. As opposed to apps and sites specifically targeted at people of color, Tawkify will connect you with a dedicated matchmaker who is interested in getting to know exactly what makes you tick and what you’re looking for in a life partner. We understand that finding your perfect match doesn’t just mean having the same taste in TV shows or eating out—it means clicking on a cultural level as well.

How Tawkify Matchmaking Works Chicago

Our proven process for lasting connection (without a single swipe)


Meet a Matchmaker in Chicago

As a client, you’ll be paired with one of our expert matchmakers in Chicago, with access to matches in your area: from across the country.


Tell Them What Makes You Tick

Forget basic dating profiles. Your matchmaker will spend the 1:1 time to really understand you: your values, your ideal partner, your likes and what gives you the ick.


Get Personalized Coaching

87% say that coaching has improved their ability to date successfully and made their matchmaking experience better. All of our client receive coaching as part of their matchmaking service.


Sit Back and Relax

No more swiping. Relax as your team works for you, vetting and video-screening each of your potential matches. Once you are matched, they’ll even plan the date based on your preferences.


Start Meeting Matches in Chicago

After every date, you can provide your matchmaker with feedback on how it went, to ensure you are only meeting people you click with.


Find Your Person

Tawkify is designed to find your perfect partner; you will have access to 1:1 coaching, private events, and premium relationship advice content from the experts. Begin your Chicago love story today!