5 Best Dating Sites in Chicago

By: Michele Baird
Updated: January 28, 2023
Couple dating in Chicago

Whether visiting the Navy Pier or enjoying an architecture river cruise, Chi-Town has lots to offer to residents and visitors. Despite its many attractions, finding a date in Chicago can be a nerve-racking experience. This is because Chicago is a fast-paced city.

Fortunately, some super dating apps in Chicago can help you connect with like-minded singles. Herein, I present the best apps for casual dating, love, marriage, the best overall, and more. Let me help you find love!

Top 5 Dating Apps in Chicago

Below are the best dating sites in Chicago:

1. eHarmony - Best Overall


eHarmony isn’t about superficial, instant attraction. So, look away if you’re only interested in just fun. This dating site is beyond that.

This site is all about finding meaningful relationships that could lead to something serious, like marriage. It has an even pool of Chicago males and females who are interested in genuine relationships.

It’s my number 1 site because it guarantees matches. If you’re displeased with your first three months’ matches, eHarmony will offer you three free additional months to try your luck.

eHarmony conducts thorough pre-screening to ensure it matches you with singles interested in long-term relationships. All new members undergo personality tests that identify their character traits.

The match success rate at eHarmony is unbelievable. This site is responsible for about 75% of online marriages. It’s the perfect site for divorced or separated Chicagoans looking for a second shot at love.

This dating platform also suits 50 plus seniors who are still seeking their special ones. I also recommend this site to anyone interested in finding a Christian single.

2. Elite Singles - Runner Up, Best Overall


Elite Singles is another dating platform for Chicago singles seeking committed relationships. It primarily caters to educated, more established singles. It has no place for people looking to play games.

It’s all about the quality of singles on this site. About 80% of members have a bachelor’s degree or some form of high-level training. Here, you can find a romantic partner who understands and lives your 9 to 5 lifestyle.

When you sign up, you’ll encounter a detailed personality questionnaire and a manual profile verification. These processes establish compatibility and weed out fake profiles.

If you’re single and seeking to find a Chicago partner going places in life, Elite Singles is where you should be.

This platform will also serve you well if you’re an over 50 stag looking to find your special love. This site also has a fraud detection system that prevents seniors from falling prey to fraudsters and catfishers.

3. Christian Cafe - Best for Faith-Based Dating

Christian Cafe signup page

Online dating can, at times, be scary to Christian singles in Chicago. Finding someone who shares your faith, values, and lifestyle can be challenging. But before you give up, please check ChristianCafe.

This dating site pairs Christian singles who are seeking marriage, friendship, or dating. As such, the platform has strict rules which you must follow.

ChristianCafe allows you to specify your searches. Besides the age and location, you can narrow your search to the level of Christian faith, church denomination, and church involvement.

Whether you’re a Catholic, Orthodox Christian, or Apostolic Pentecostal, you’ll find your match on this dating platform.

ChristianCafe befits Chicago singles seeking serious commitments with other Christians.

With that said, this site offers more than matchmaking services. It has a forum where you can find support, fellowship, and advice from other Christians.

4. Silver Singles - Best for Senior Dating

Silversingles Online Dating Signup Page

Silver Singles is a leading senior dating site that suits the over 50 crowds. As a senior matchmaking site, it best suits Chicagoans seeking serious relationships.

This platform is available on the web or via a mobile app. It has a thorough signup process that involves profile verification and fraud detection. Its interface is simple, and seniors can easily send messages and smiles.

Unlike other dating sites, women make up 59% of the singles pool at Silver Singles. Straight men have a variety of options here.

If you’re a woman, you can rest assured men won’t bombard your inbox with unwanted messages. This female-friendly site allows you to take control of your dating experience.

Silver Singles is the perfect dating network for retirees looking to find true love in their sunset years. Here, you’ll find mature singles with similar values, lifestyles, and experiences.

The diverse pool of members on this site makes interracial dating simple.

If you’re an LGBT senior in Chicago, you can find your perfect match using this dating site.

5. Catholic Match - Best for Catholic Dating

Catholic Match

Catholic Match has the largest collection of Catholic singles in the United States. If you’re in Chicago, you can use this site to find a partner who shares your Catholic beliefs.

This site suits devout Catholic singles who are seeking a faith-focused relationship.

Catholic Match is my number 5 dating site because prominent Catholic leaders recommend it. Many successful marriages can trace their roots to this site.

Signing up is pretty intense. You have to provide information regarding your interests, faith, background, and lifestyle. Things that help create a match include the number of times you attend a mass and your views on:

  • Holy orders
  • Papal infallibility
  • Premarital sex
  • Sanctity of life

These detailed questions enable you to match with profiles with similar interests.

Catholic Match constantly monitors profiles and may suspend a user if they have a questionable reputation.


Which dating site has the highest success rate?

eHarmony has the highest success rate among the dating sites. 75% of successful marriages that begin online can be linked to eHarmony.

What is the best hookup site in Chicago?

The best hookup site in Chicago is Adult Friend Finder (AFF). A huge chunk of AFF’s active users lives in Chicago. Whether you’re seeking a friend with benefits, a casual encounter, or some kinky evening moment, you can trust this hookup app to deliver.

What is the best dating site for over 50 or seniors in Chicago?

The best online dating sites for seniors in Chicago are eHarmony and Silver Singles. eHarmony is an ideal haven for seniors seeking serious companionship, while Silver Singles is an exclusive dating platform for those over 50s.

Both sites carry out in-depth pre-screening to help prevent seniors from falling prey to fraudsters.

Which dating site is best for serious relationships?

eHarmony is the best online dating platform for serious relationships. Nearly all singles in eHarmony are interested in long-term commitments and not short-term fun.

Key Takeaways for Singles in Chicago

Chicago aerial view

The city you live in can have a massive influence on how you date. And that’s the case with Chicago, IL. As a single person in Chicago, you might find difficulties approaching your crush in streets or bars. Everyone seems busy.

Luckily you can use online dating sites to find your perfect match. Whether you need a casual encounter, a Christian partner, or a long-term engagement, you’ll find an online app that caters to your needs.

Is Chicago Good for Singles?

Yes, Chicago is good for singles. About 60% of Chicagoans are single, meaning it’s easy to find an unmarried person using dating sites.

Chicago is also religiously, ethically, and culturally diverse. This means you have plenty of options when it comes to dating.

Free Dating Sites in Chicago

The problem with most of the free dating sites is either they will sell your data, or you will face a lot of fake accounts and scammers. So it’s better to go for a premium site that offers a free trial.

Most of the mentioned sites aren’t entirely free. They offer a free trial period and will bill you once this period elapses. 

Here are the free trial links for the most popular dating apps in Chicago:



Free Trial Link




Elite Singles


Christian Cafe


Silver Singles


Catholic Match