Fact Checked by: Dr. Nicolette Natale
Fact Checked by: Charles Roscopf, CPA
When you live in a big city like Chicago, most people think finding love is a breeze. There’s tons of beautiful people walking around, so you should just be able to walk outside and find love, right?
Wrong. Before you get sad, though, we have good news to share. Another perk of living in the Windy City is that matchmakers in Chicago are ready to help you find that special someone. These experts help to bridge the gap between you and the singles that seem so close yet so far away.
But just as it’s important to pick out a great mate, picking out the right Chicago matchmaker is equally important. You need someone who understands you, has a real pulse on the 2.7 million people in the city, and can make introductions that set you up for romantic success.
Let’s take a look at the four best Chicago matchmakers now.
1. Three Day Rule Chicago
Chicago Matchmaker Effectiveness Testing Score: 8.9/10
Named after a famous dating cliché, Three Day Rule is the no-competition, hands-down leader for matchmaking services in Chicago. Unlike some of the the “bigger” players in the industry that try and serve everyone everywhere, Three Day Rule focuses on 11 main cities in the US—Chicago being one of them.
Let’s take a quick look at the biggest pros and biggest potential drawbacks, so you can decide if it’s a good fit for you. There are two main pros that come to mind with Three Day Rule. One—the matchmaking process is incredibly detailed, dials in to what you want AND what you don’t want, and gets you matches who fit into exactly what you’re looking for. This may sound like it should be a given for a matchmaking service, but it’s not.
Two—you get some added bonus perks just for being a member. The two biggest are free professional dating coaching and a free professional photoshoot (and you get to keep the pictures). No matter what membership level you choose, you get these at no extra charge.
For drawbacks, as you probably expect, a personal Chicago matchmaker is going to be more expensive than a traditional dating app. Three Day Rule membership prices start at $5,900. Compared to other matchmakers, this is comparable (and arguably less expensive with the added amenities). Still, depending on your situation, it may be a bigger investment, which we wanted you to be aware of. That said, if you end up meeting your forever person, probably the best investment ever.
If you have more questions, want to get a feel for the program, or are ready to get started, the link below will set you up with a 100% free consultation call with a Three Day Rule matchmaker. If you’re at all interested, at the very least you should at least set up a call and get more info.
2. It’s Just Lunch Chicago
Chicago Matchmaker Effectiveness Testing Score: 6.94/10
One of the most well-known brands in matchmaking in the city of Chicago is It’s Just Lunch. Founded all the way back in 1991, the brand has been helping to match singles for over three decades. One nice perk about It’s Just Lunch Chicago is that matches are limited to Chicago and the surrounding suburbs. In some other cities the company services, the net gets cast fairly wide, so you could end up with a match from a bit of a ways away.
The matchmaking team for the area has six women on it (five matchmakers and one CEO of the area), but no men—which is not that unusual, but something we did want to point out.
Unfortunately, there is one big elephant in the room that needs to be mentioned about It’s Just Lunch. The company was sued in a class-action lawsuit that claimed the service was a “a massive scheme to defraud tens of thousands of single professionals throughout the country.” The case dates back to 2007 but was finally settled in 2019 where the company was forced to pay just under $5 million to clients.
We’ll let you be the judge of whether or not the company has changed its ways as this stems from quite a ways back, but we wanted to make sure you at least had all of the information.
3. Tawkify Chicago
Chicago Matchmaker Effectiveness Testing Score: 7.92/10
With over 200,000+ matches to date, a decade in business, and 1 million+ singles in the network, Tawkify is a pretty popular option in a lot of cities—including Chicago. What’s neat about Tawkify is you have two different types of service you can select, both with different advantages as well as price points.
The first option is to be part of the network, which means you could get tapped at any point in time to be a date for someone who is a client (the second option). You won’t have a matchmaker actively looking for you, but you’ll be in the database for a match. It’s only $99 a year, but there is no guarantee that you’ll see anything come from it. It’s basically a way to roll the dice to get another “pole in the water”.
The second option Tawkify offers for Chicago singles is its client experience. This is where you have a dedicated, real-person looking for matches for you. Pricing on this can range anywhere from a few thousand dollars up to tens-of-thousands, depending on what you’re looking for.
If you’re curious, we’d encourage you to schedule a free consultation with a matchmaker today through the link below.
4. Matchmake Chicago
Chicago Matchmaker Effectiveness Testing Score: 7.55/10
No, we didn’t make a typo leaving the ‘R’ off the end of Matchmake in the company’s name—that’s the actual name. If you’re looking for something a little smaller and more localized, Matchmake Chicago could be an option you’re interested in. From what we’ve gathered, it’s a very small team of two matchmakers—Lisa and Anna. The duo has been on several local news programs in the area, which does show that they truly are a local-only option.
Some of the services offered by Matchmake Chicago include quality introductions (matchmaking), date planning ideas, and personal coaching if you need it.
The one drawback we see potentially being an issue would be the size of the company’s network. We’d hope in a city as big as Chicago this isn’t a big issue, but we don’t see any claims on the company’s website talking about how big their network is. Additionally, during our last review, the company’s website still showed 2022 at the bottom of the page, which isn’t a great sign of consistent updating being at least a year behind.
But—they truly are local and could be an option worth trying.
Testing Criteria and Methodology
Here is the criteria we use when testing Chicago matchmakers.
| Factor | Weight | Description |
|---|---|---|
| Quality of Matches & Personalization | 25% | Measures how well the service tailors matches to client preferences and avoids “cookie-cutter” pairings. |
| Local Focus & Community Knowledge | 20% | Reflects how well the service knows Chicago-specific dynamics, from neighborhoods to cultural nuances. |
| Privacy & Discretion | 15% | Assesses confidentiality practices and how well personal data is protected. |
| Reputation & Client Feedback | 15% | Looks at online reviews, legal history, and overall community reputation. |
| Affordability & Value | 10% | Examines whether pricing feels fair relative to outcomes and competitors. |
| Scale & Database Size | 10% | Considers how many singles the service can access locally and regionally. |
| Extras & Client Experience | 5% | Reviews value-adds like coaching, photoshoots, and proactive communication. |
Individual Testing Results – By Service
Here are the results of our testing broken down by data category and service.
Three Day Rule Chicago Results
| Factor | Score (0-10) | Weight | Weighted Score | Notes |
|---|---|---|---|---|
| Quality of Matches & Personalization | 9.8 | 25% | 2.45 | Three Day Rule Chicago delivers exceptionally tailored matches. Clients report feeling deeply heard regarding both what they want and what they don’t want, helping avoid the frustration of mismatched introductions. |
| Local Focus & Community Knowledge | 9.2 | 20% | 1.84 | Operates a dedicated Chicago team who understand city-specific dynamics like North Side vs. South Side cultures, professional circles, and suburban commuting patterns. |
| Privacy & Discretion | 9.5 | 15% | 1.43 | Highly confidential, with private consultations, protected personal data, and discreet communication. |
| Reputation & Client Feedback | 9.0 | 15% | 1.35 | Widely respected in Chicago for professionalism and results. Occasional complaints exist (like any service), but they’re rare and generally minor. |
| Affordability & Value | 7.8 | 10% | 0.78 | Starting at $5,900, it’s not cheap, but clients find it reasonable for the personalized service and included perks like coaching and photoshoots. |
| Scale & Database Size | 8.5 | 10% | 0.85 | Solid local database, though not as massive as national giants. Still sufficient for Chicago’s dating scene. |
| Extras & Client Experience | 10.0 | 5% | 0.50 | Offers valuable extras like free professional coaching and photoshoots, a standout benefit compared to many competitors. |
| Total | 8.90 |
It’s Just Lunch Chicago Results
| Factor | Score (0-10) | Weight | Weighted Score | Notes |
|---|---|---|---|---|
| Quality of Matches & Personalization | 6.8 | 25% | 1.70 | Offers personal matchmaking, but experiences vary. Some Chicago clients report generic matches lacking true personalization, while others praise the simplicity. |
| Local Focus & Community Knowledge | 8.5 | 20% | 1.70 | Operates specifically in Chicago and suburbs, helping ensure matches don’t live unreasonably far away—a significant advantage in a sprawling metro area. |
| Privacy & Discretion | 8.2 | 15% | 1.23 | Maintains solid privacy standards, though past lawsuits raise trust concerns for some clients. |
| Reputation & Client Feedback | 4.2 | 15% | 0.63 | Reputation has taken hits due to a class-action lawsuit and mixed client reviews. Some people swear by the service; others feel misled. |
| Affordability & Value | 5.5 | 10% | 0.55 | Prices are steep for a service that may not consistently deliver quality matches, reducing perceived value for many Chicagoans. |
| Scale & Database Size | 8.5 | 10% | 0.85 | Large national network ensures a good pool of singles, though local focus limits this to Chicago and suburbs. |
| Extras & Client Experience | 5.5 | 5% | 0.28 | Offers limited value-added services compared to competitors; experience is largely traditional and straightforward. |
| Total | 6.94 |
Tawkify Chicago Results
| Factor | Score (0-10) | Weight | Weighted Score | Notes |
|---|---|---|---|---|
| Quality of Matches & Personalization | 8.2 | 25% | 2.05 | Delivers personalized matchmaking with dedicated matchmakers, though some clients report mixed experiences and less consistency compared to boutique services like Three Day Rule. |
| Local Focus & Community Knowledge | 7.8 | 20% | 1.56 | Operates in Chicago but lacks as strong a hyper-local focus as purely local firms. Some matches may be outside client comfort zones distance-wise. |
| Privacy & Discretion | 8.5 | 15% | 1.28 | Maintains good privacy practices with confidential communication and protected client information. |
| Reputation & Client Feedback | 7.2 | 15% | 1.08 | Reputation is generally positive, but some reviews highlight feeling like “a number” in a large system rather than receiving truly boutique service. |
| Affordability & Value | 7.0 | 10% | 0.70 | Costs range from affordable “database” membership ($99/year) to high-end services costing tens of thousands, leaving some confusion over value. |
| Scale & Database Size | 9.2 | 10% | 0.92 | National database of over 1 million singles offers significant reach, though the truly local pool remains less defined. |
| Extras & Client Experience | 6.5 | 5% | 0.33 | Some coaching and extras are available, but not consistently bundled into base packages like with Three Day Rule. |
| Total | 7.92 |
Matchmake Chicago Results
| Factor | Score (0-10) | Weight | Weighted Score | Notes |
|---|---|---|---|---|
| Quality of Matches & Personalization | 7.2 | 25% | 1.80 | Run by two local matchmakers, offering highly personal service. Clients feel heard and appreciated, though limited team size means less bandwidth for many clients at once. |
| Local Focus & Community Knowledge | 9.0 | 20% | 1.80 | Purely local with deep knowledge of Chicago neighborhoods, social scenes, and Midwestern culture, creating strong matches for clients who value local insight. |
| Privacy & Discretion | 8.5 | 15% | 1.28 | Highly discreet, maintaining confidentiality in all client interactions, though lacking robust tech infrastructure larger firms use for data security. |
| Reputation & Client Feedback | 6.5 | 15% | 0.98 | Reputation is generally positive among local clients, but small size and outdated web presence raise concerns about scalability and staying current. |
| Affordability & Value | 8.5 | 10% | 0.85 | More affordable than large firms, making it appealing to Chicagoans seeking boutique service without NYC-level costs. |
| Scale & Database Size | 5.0 | 10% | 0.50 | Small network limits match possibilities despite deep local knowledge, especially for clients with very specific preferences. |
| Extras & Client Experience | 6.8 | 5% | 0.34 | Offers coaching and date planning, but lacks major value-adds like free photoshoots included with bigger services. |
| Total | 7.55 |
How Much do Matchmakers in Chicago Cost?
As you may very well already know, having a one-on-one person assist you in finding love does come at a higher price tag. While many of the best dating apps out there are around $30-$60 per month, Chicago matchmakers can run you anywhere from a few hundred dollars all the way up to several hundred thousand for VIP and elite services.
Here’s the bottom line on Chicago matchmaker pricing—you’ll get what you pay for with a reputable company. At the lower end of the pricing, you may get access to be included in the network like with the $99 per year option from Tawkify. From there, the personalization increases with the pricing.
Matchmaking in Chicago – What to Know
Before we send you on your merry way, our team wanted to share a few things specific to matchmaking in Chicago that we think will be important to you. Ideally, these tips and bits of information can help you understand a lot more about the process in your city.
- Chicago is one of the leading markets for matchmakers. – There are a select handful of cities in the US that are hot beds for matchmaking services. As you might expect, these include cities like LA, NYC, Atlanta, Boston, and Chicago. According to search volume trends, Chicago ranks 4th for the most traffic among all cities in the US. What this means is that your chances of success here as opposed to a smaller Illinois city like Aurora or Springfield are much higher.
- Executive heavy cities like Chicago do well with matchmaking. – One of the biggest selling points of matchmaking services is the time you save. In cities like Chicago where there are a lot of industries that attract busy executives, expect to see a lot of people turning to these services. This means bigger databases and better chances of positive results for Chicago users. This is why you see Chicago included as one of the 11 cities covered by our leading option Three Day Rule.
- There are 12 Chicago matchmaking companies listed on Google. – While this might not sound like a lot of businesses, it’s actually quite a few. When it comes to options, you have plenty in Chi-town. That being said, they’re not all going to be great, which is why we took the time to lay our out favorite Chicago matchmakers.
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