The 7 Best Dating Apps & Sites in Chicago

Looking for dating sites in Chicago?

Then this article will help you find the best apps & sites to use in Chicago. 

Dating websites and apps have taken over our love life and I can’t fault them, if you use the one that fits best to what you’re looking for, you stand a great chance of finding the perfect someone for some good times.

And that someone will make your nightlife just so much better.

Without further ado, 

What is the Best Dating Site?

Here are my 3 top picks for the best dating website to try this year. I’d mostly recommend using our #1.


Best for meeting hot singles ready for action. is a dating app for those who are looking for the one and only and not just a hookup. Users can choose between a 3-month, 6-month or 12-month plan, then start reviewing potential matches that may be compatible with them. The best part about this app is its algorithm, which has been designed to respond to both geographical preferences as well as personal preferences such as religion and sexuality.

It is one of the oldest and most popular dating sites out there with over 40 million people visiting every month. It has a very user-friendly interface that allows you to browse members by their interests, age, and location. The site also offers apps for those who want to take their search on the go.


Best for meeting single people looking for hookups.

Adultfriendfinder is a dating site for adults who are looking to have casual hookups with other people. The site offers a wide variety of features, including live webcams, chat rooms, forums, articles, county listings, personal ads, photo galleries, and more. Adultfriendfinder was created in 1995. It has grown steadily since then and hosts over 7 million members online. The site has an average of 100k visitors every day – the majority are male.

The site is not all about just hooking up. Yes, you can find that here if that is your particular flavor or fetish. But for most members, the site is more geared toward friends with benefits.


Best for couples looking to expand their horizons.

When it comes to dating apps, they are all about the same. 99flavors is no different. If you are looking for something more traditional, this app is not for you. But if you want to have a little fun with your love life, this app has some great features that will make it worth the download. It’s tailored especially for swingers, couples looking for extras, or singles looking for couples to play with. is a dating site founded in 2012 that’s designed to be fun, easy, and inclusive. It features a variety of different singles, couples and swingers from all over the world.

Dating Apps & Sites to use in Chicago

Chicago — the Windy City — is probably one of the most challenging locations on the planet to find love. With more than 3 million people and an exciting night life in the city, it seems like finding someone amazing must be easy, but that is not what happens. 

Fortunately, the finest dating sites in Chicago are masters at filtering through the clutter and bringing people together.

Here is the list:


tinder dating app

Anyone who is even slightly familiar with the world of online dating has heard about Tinder, arguably one of the most famous mainstream dating apps. I can even go as far as to say that the word ‘dating app’ is synonymous with ‘Tinder’! Founded in the year 2012, Tinder has grown into the most famous dating app used worldwide. Although it was intended to be an app used for casual dating or hookups, people started meeting their potential partners on Tinder!

No matter what device you are on, you can easily download the free app, sign up within minutes, and you’re set. It’s a completely hassle-free process that most people love. Fortunately, Tinder doesn’t allow users to send messages without first matching with someone. This is great, because who wants to open up their dating app and find a dozen creepy dudes lingering in their inbox, right? Tinder renders its excellent services to almost every country in the world, including Chicago!

The League

You are allowed to be quite selective about your choices in the League, including selecting which ethnicities you want to date; our guts churn a bit when we hear that. 

To be considered for the app, you have to first register by providing your LinkedIn account, present employment status, and institution attended. So, okay, it’s a tad egotistical. Members are of different ages, although the majority are in their early twenties. This application also does not allow an imposter to use it. For authorization, you have to connect your social media and LinkedIn accounts. The League is famously tough to get into, so imposters whine about it on TV. The site is now available in 30 locations throughout the country, including Chicago, where it has been for quite some time. You got it correct: the League is making it difficult for people to win. And yet, it appears to be running successfully; People are still eager to join.


The idea behind this free application was to create a relaxed online dating environment. It’s similar to getting a cup of tea with a friend, but only digitally. The atmosphere is designed to be laid-back so that strain does not interfere with your dating life. CMB offers you seven alternatives every day, all of which are carefully chosen using their pairing technology. Bagels are the name for these pairings that the app gives. The bagels only remain only for a week; this, therefore, persuades people to follow up themselves.  If you genuinely admire someone, you should make an effort to contact them. 

Another explanation why CMB is so successful is that this technology considers your past activity when choosing your future set of brand new bagels. Instead of just relying on a quiz, it understands your tastes and patterns by closely monitoring your activity. Small chat is good for you, but the real bonding occurs when you meet someone directly.  The app’s seven-day conversation restriction deters ghosting and fosters actual dates, whether digital or in real life. Since singles hit the dating scene in Chicago mostly in winters due to the cozy evenings, hitting these sites during peak time is the best way to go!

Silver Singles

SilverSingles is a genuine 50+ dating site. This implies that if you happen to be amongst the over-50 individuals seeking love and friendship in Chicago, this dating service is the place to be. The majority of other dating services for the older demographic will only display accounts of individuals in your area. SilverSingles goes above and beyond that. Every member takes a personality assessment so that the algorithm can learn more about them.

There are two levels of subscription on this app: free and paid. To check the software, the firm suggests utilizing the free subscription. SilverSingles’ privacy is multi-layered. To keep customer data safe, the site employs SSL encryption, data encryption, and identity verification technologies. Newcomers are also subjected to regular profile inspections. It is accessible on Android and iOS, but it may also be accessed via the webpage on computers or other devices.


Jdate was founded in 1997 as a member of Spark Networks, amongst the sector’s most potent dating website companies. JDate has gone through numerous refinements since then, but it has maintained its appeal amid Jews. Despite its niche audience, the service is available to people outside Judaism as well — but only if users declare their intentions of converting to Judaism later. 

Daily, the dating system suggests many prospective dates, but individual searches may also be conducted by simply adjusting the parameters. JDate is completely free to join; however, if you wish to communicate, you must subscribe to a premium upgrade to enjoy all the perks. The only aspect that may be irritating to most is that the interaction can only be done upon payment, although you can easily fix it by making a minimal fee payment. If you belong to the Jewish community residing in Chicago, JDate is an excellent platform for you to meet with your significant other.


Are you a fitness Freak who leads an active lifestyle and wants to have a strong bond? If your answer is yes, the newest matchmaking site on the store could be right for you. At last, a dating website for energetic, inspired people who want to get things done. GoGetter connects people based on what means most to them: a similar lifestyle and complementing personality types. It was indeed developed by a Professional Matchmaker and Relationship Coach and even by a top athlete. 

It’s a compatibility-driven matchmaking tool. After you get paired, each person must spend a penny to communicate with one another. In this manner, you both are equally involved and committed to taking the bond further.   You receive your penny back in case the other individual does not spend! Easy! You can benefit from the video biographies to not only display your charm but also assist you in figuring out if there’s a bond worth considering. Like all other sites, GoGetter has both a free version and a premium one.


In this day and age, women’s empowerment and safety are paramount to online dating. Due to failed attempts to match authentic users or have their inboxes frequently penetrated by creepy, persistent men, women often find online dating experiences less than enjoyable. Thankfully, Bumble understands this all too natural problem and has decided to give women back the power. Like Tinder, Bumble also has free and paid options. And again, just like Tinder, the free option isn’t too restrictive. 

You can create your profile, match with users, and even chat and send messages, which is excellent. Since the app asks permission to sync with your social media accounts, the lengthy sign-up process is relieved off your shoulders. The app automatically imports all your information, allowing you to begin browsing within minutes. The suggestions begin almost immediately. There is no tedious quiz or questionnaire process which will take up a couple of your hours. 

Quick Tips for using dating apps in Chicago

Be careful of what you say

Don’t instantly think that members of a dating site don’t communicate with each other. You could get caught redhanded if you tell one person how much of a free spirit you are while pretending to be a bit of a loner to entice another.

Consider premium subscriptions 

Users of premium sites are more likely to be genuine about dating. Your findings aren’t assured in either approach, but if you don’t think about paying a few dollars for a temporary membership, you might end up wasting resources.

Be clear about your intentions.

If all you want is to stick around for a while, say so politely. If you’d rather be buddies before even getting into a relationship, say so. You shouldn’t disguise your motives; they’ll ultimately be revealed.

Avoid posting deceiving pictures of yourself

Individuals don’t always appear like they do in their finest photographs. However, if you do,  that’s fantastic. If no, posting your finest one will simply hook you straight for disappointment. Rather, upload regular, daily images of yourself, avoiding any photographs where the sunlight hits you just so and makes you look like someone you’re not.

Don’t obsess

If you send a text to somebody you believe is a beautiful fit for you, don’t get too worked up if you don’t receive a response. All of us are unique; therefore, if somebody isn’t interested in you, quickly clear the way and hop on to other grounds. 

Frequently Asked Questions on Dating Apps in Chicago

Which is the most popular dating site in Chicago?

Tinder is the most popular dating app used in Chicago. This free application is the mafia when it comes to the dating world. Bumble is the second most popular on the list after Tinder. 

Where to date in Chicago?

There are numerous romantic activities to do in Chicago, and a lot of unique experiences to enjoy with your significant other. Chicago boasts a magnificent view and a superb lakeside. The beautiful suburbs are ideal for strolling while holding hands. Celebrations, literature, artwork, theater are all available.

How do I know which site is best for me?

The first step into online dating life is to choose the right site. If you’re looking for a fling, then Tinder or CoffeeMeetsBagel can be your savior. However, if you seek a meaningful long-term relation, sites like SilverSingles and The League should be your choice.

Is Chicago a good city for dating?

According to a new study, Chicago is a great place for singles to find their soulmates. The city has vast dating opportunities thanks to the ever-increasing demand for online dating sites in this area.

In conclusion

It is said that the water is teeming with fish. And there’s plenty of it in Chicago. The Windy City follows a somewhat distinct set of dating regulations. Whether it’s due to the abundance of choices or two degrees of separation from an old ex, the dating scene here is unique. However, one should not lose hope. True love can be found anywhere with the right choice of an online dating app.

Keep exploring!

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