Finding love in the Windy City can sometimes feel like you’re doing the best you can but running headfirst into those in-your-face winds on Lakefront Trail. Why? Well, Chicago may be home to 2.7 million people, but it’s a fast-paced city where everyone always seems to be in a hurry.
Most people in Chicago we talk to say they’ve tried everything — dating apps, friends, family, happy hour, work — and nothing has seemed to pan out. But there is one other option that’s quickly becoming popular in Chicago. We’re talking about professional matchmaker services.
If you’re thinking about hiring a one-on-one professional to help you find love in Chicago, there are some things you’re going to want to know first. Let’s get into it.
1. Chicago is home to local and national matchmaking services.
If you’re looking to hire a matchmaking service in Chicago, the first decision you’ll need to make is between a national brand or a local company. While in other industries we’re big fans of buying local, there may be some challenges with that idea when it comes to matchmaking services.
In theory local Chicago-based matchmakers should be better. They know the city better, they’re in-tune with the locals, and you can meet with them in person. The problem? It never works out that way. Local matchmakers tend to have small pools of singles, fewer resources to support you, and smaller staffs that may be overloaded with clients.
Does this mean you have to settle for a big box national matchmaking service? Thankfully, no.
Our recommendation for the best Chicago matchmaking service is Three Day Rule.
Our top pick for the best Chicago matchmaker is a company that currently operates in only 15 cities throughout the country — including Chicago. The company was recently acquired, which means there’s a lot of new money and resources being pumped into the business. The result is a Chicago matchmaking service that has the power and reach of a national brand, but is only in 15 cities —so you still get the local touch.
The company we’re talking about is Three Day Rule. If you want to learn more about them (and see how to schedule a free consultation call), check out our Three Day Rule review now.
Other Chicago matchmaking services
Besides Three Day Rule, there are other matchmaking options within the city. While the quality may be hit or miss, we want to be as thorough as possible by letting you know what may be available.
First, here are a few of the local options in Chicago.
- Stef and the City – Probably the most well-known local option in the city. Good testimonials on their site (that they uploaded), but the most recent is from 2019 which gives us some questions about the amount of effort being put into the company.
- Chicago First Dates – This company lists itself in directories as a matchmaker, but in reality they’re a speed dating company with a website that looks like it was made in 1990.
- Birds of a Feather – This was an interesting one that we only found when searching Chicago business records. It’s an “ethically non-monogamous, polyamorous” matchmaking service. In other words, if you want to date several people and want a matchmaker to help get you connected, this might be for you as most other Chicago matchmakers only deal with monogamy.
- Matchmakers of Chicago – [Out of business]
And here are a few of the national options in the city.
- Tawkify – Large national provider with over a million members in it’s matching pool. Read more about them in our Tawkify review here.
- Ambiance Matchmaking – This company is a national brand in 11 cities founded by Leslie Wardman. From our research of Illinois business records, it looks like the company is headquartered (or at least has an office) in Chicago. The company’s website says they’ve been in business for over 20 years, but the business license we found for Ambiance Matchmaking LLC was registered in May of 2023. Either we’ve got it wrong and they’re different companies, or something doesn’t quite add up here. That said, the company’s name in their Privacy Policy is listed as “Ambiance Matchmaking LLC” so it seems like the same company to us.
- It’s Just Lunch Chicago – As one of IJL’s franchises, It’s Just Lunch Chicago’s team of six is quite active on the local news and media scene. Before you consider signing up, though, make sure you read our article about It’s Just Lunch’s $77 million lawsuit.
2. For a city with 2.7 million people, the number of matchmaking services is limited.
Something we found surprising about the matchmaking industry in Chicago is that there weren’t a whole lot of options like we’re used to seeing in other cities. For example, we found over 130 matchmaking services in NYC.
In Chicago, though, far fewer. Here are the receipts.
When we searched for matchmakers on Yelp, we got 108 results. However, the majority of these were executive matchmakers (like for a job), out of business, or some other business like a relationship counselor.
When we searched the entire state of Illinois’ business license records for ‘matchmakers’ and ‘matchmaking’ keywords, we only found seven active companies and only two of them looked to be actual matchmakers (Ambiance Matchmaking LLC and Birds of a Feather Matchmaking LLC — both discussed earlier).
Surprising? Very. While we didn’t expect as many local matchmaking services as in NYC, we expected at least a few more than what we found.
3. Chicago’s fast-paced, professional culture is a good match for professional matchmaking.
According to the U.S. Bureau of Labor Statistics (BLS), as of November 2024, there were 1,134,000 people in Chicago who worked in finance, professional services, and business services.
When you understand how matchmaking services work, you quickly see that they’re heavily geared toward busy professionals who want results but don’t have the time to troll bars or downtown Chicago happy hours. With over 40% of Chicago working in these types of professions (and probably more within the other categories), you end up with a city that is perfect for professional matchmaking.
You won’t find a single national matchmaker who doesn’t have dedicated resources specifically for the city of Chicago.
4. The pricing for Chicago matchmakers ranges from a few thousand dollars up to $300k+.
The range of pricing for Chicago matchmakers starts at a few thousand dollars and goes all the way up to several hundred thousand dollars for VIP-level services.
The average price of a Chicago matchmaking service is between $3,500 and $10,000. The exact cost depends on the provider you choose and which package you choose.
There is a lot of wiggle room when it comes to how much matchmaking services cost. Make sure you ask a lot of questions and ensure you get a price and a package that fits your needs (and that you’re comfortable with).
5. Many Chicago singles still choose to use traditional dating apps.
If those prices are above what you’re looking to spend when hiring a Chicago matchmaker, there are other options. Many traditional dating apps now employ complex algorithms that work like matchmakers, just without the one-on-one touch. You will have to do a bit more of the work, but you’re going to save quite a bit of money.
For example, one of our favorite picks for a traditional dating app is eharmony. While a Chicago matchmaking service will cost you several thousand dollars, eharmony memberships start at around $20 per month. And, unlike professional matchmakers, sites like eharmony even come with free trials to check things out before you buy.
If this is more your speed for finding love in Chicago, check out our guide to the best dating apps.