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The 10 Best Dating Apps and Sites in Chicago That Will Work For You In 2024

A beautiful woman you might meet on the best Chicago dating apps

According to the most recent census data, Chicago has over 60% of single men and women living throughout this vibrant metropolis. With numbers like these, you’d think that finding a partner would be a breeze in the Windy City. Well, think again because finding the best dating apps in Chicago that will work for you can be a challenge.

Finding a date post-pandemic has made most single people even more hesitant to approach strangers in public. Even the act of walking to the bar with the goal in mind of finding a date can be nerve-racking. Dating apps and websites surpass this “scary” aspect. They shoot you straight past the “Can I get your number?” phase and plunk you straight into the “What time works best for you?” phase. More and more people are joining these platforms and it’s quite clear why: they work. But which are the best dating apps in Chicago? Let me give you a sneak peek:

With that in mind, let’s have a look at more dating apps and sites that work in Chicago.

Methodology: How We Recommend the Best Dating Apps in Chicago

To bring our readers a comprehensive list of the best places for hookups in Best Dating Apps in Chicago, every BeyondAges contributor follows strict and verifiable guidelines. Unlike other dating sites, our reviews are always up-to-date and sourced by local experts–not rehashes of stuff you can find elsewhere. 

Aspect Approach Description Criteria for Writers Editorial Standards
Targeted Testing Performing detailed assessments of dating apps with a focus on features and strategies effective for men dating in Chicago. Each app is used extensively to ensure a comprehensive understanding of its local suitability. Writers must be familiar with various dating apps and have a solid grasp of the dating landscape in Chicago. Editors ensure reviews are thorough, locally pertinent, and maintain clarity and accuracy.
Chicago Dating Experience Drawing from the real-world dating experiences of our team in Chicago to evaluate each app's practicality for local men. The team's insights offer a realistic view of app effectiveness in the city. Writers need firsthand experience in Chicago’s dating scene and the ability to contextualize it within broader dating dynamics. Editors prioritize content that is relatable and practical for Chicago-based users.
Dynamic Adaptation Continually exploring new dating approaches and trends in Chicago to keep advice relevant and effective for local men. This includes city-specific strategies tailored to Chicago's unique dating environment. Writers are expected to stay abreast of the latest dating trends and changes in Chicago’s social dynamics. Editors ensure that content is current, integrating the latest trends and data.
Chicago Online Focus Focusing on the impact of online dating and digital communication within Chicago’s dating scene. This involves an in-depth exploration of platforms popular in Chicago, assessing local pros and cons. Writers should have expertise in online and digital dating platforms popular in Chicago. Editors emphasize the local relevance and practicality of online dating advice.
Local Community Engagement Engaging with Chicago-based readers to exchange experiences and build a vibrant, city-specific community. This interaction enhances trust and tailors the dating experience to Chicago’s unique culture. Writers need to engage with and understand the Chicago dating community, promoting reader interaction. Editors foster a community-focused approach, ensuring content resonates with Chicago residents.

Author Credentials:

Hi, my name is Ryan Vine. As a regular contributing author to BeyondAges.com and a Chicago resident, I’ve found some killer secrets about Chicago dating apps that have brought great success to my readers and one-on-one clients. After many years of great success in the Windy City, I’ve made it my mission to create a body of work that helps men and women find what they’re looking for in life. Feel free to drop a comment below and start the conversation today. Best of luck!

Affiliate Disclaimer:

BeyondAges.com engages in various affiliate marketing programs. This arrangement means that we may earn a commission if you make a purchase through links in our content. It is important to note that these commissions come at no additional cost to you. We assure you that our participation in these programs does not bias our content. Our recommendations and reviews are the result of extensive research and analysis, aimed at providing the most reliable and valuable information to our readers.

Transparency with our audience is a cornerstone of our ethos. As such, we believe it is essential to openly communicate our affiliate relationships. The revenue generated from these commissions is crucial in supporting the continued production of high-quality, research-driven content. We are grateful for your continued trust and support in BeyondAges.com and remain committed to maintaining the integrity and impartiality of our content, regardless of these business relationships.

#1 - AFF is the best hookup app in Chicago

AFF screenshot

AFF is the best app right now if you're looking for something more physical and short-term. There are tons of apps out there that are geared toward relationships but only a couple that are great for something fun in bed. Of those, AFF has been the best at consistently delivering in Chicago, especially for guys.

To be the best hookup app in Chicago you really need two things, people and the right focus. With over 60 million active users (a ton of whom are in Chicago) and a complete focus on getting down to business, this is an app that delivers. If you've only used Tinder before, this is going to be a pleasant surprise. It's not just women looking for attention, people actually want to meet up.

To give you a more detailed look at how AFF works and how it performs for regular guys, you can also have a look at our Adult FriendFinder review.

If you want to start with the best hookup site in Chicago you've found it.

Why AFF is one of the best options:

  • One of the most popular apps out there and the most effective for finding a bedroom partner
  • A lot more useful for guys than Tinder has been in Chicago
  • People get right to the point

What we don’t like about it:

  • Many users can only access via web app
  • We wish they would update the design
  • The ads are not great

What people think of Adult Friend Finder

Tim - TrustPilot

Adultfriendfinder.com is pretty much one of the best options and always worth a shot if you wanna get laid. Sure there are fake profiles but use your common sense and you will be fine. If you were not lucky also check out CasualsexOnly.com. Also one of the better options out there.

Louis S. - SiteJabber

AFF has been around for a long time and it is an established community with mostly real users. I have used it in the past and what can I say: I had a blast. Messaged a countless number of chicks but actually hooked up with two of them. My advise. Just send out messages that really work, nothing like hey Hun, What's up?!... just be creative and don't forget to stay active.

You Can Try AFF Free!
If you're just looking for short-term fun you need to try out AFF's free trial. We've spent months and months testing out the alternatives (more than 100 other sites) and haven't found anything that gives most guys more options and better results. Give it a shot!

Have you tried AFF for dating and hookups in Chicago? If so, drop a comment below and tell us what you think!

Got a date? Pick one of Chicago’s safer neighborhoods:

Chicago is a beautiful city full of excitement and interesting things to do, but it unfortunately also has a reputation for high crime in certain area. To help you navigate Chicago safely, here are the least-threatening places to go in and around the city according to PropertyClub:

  • Edison Park: Crime rate is 77% lower than the rest of the city.
  • Norwood Park: Crime rate is 72% lower than the city’s average.
  • Forest Glen: Crime rate is 70% lower than in the rest of the city.
  • Lake View: Crime rate is 40% lower than in the rest of the city.
  • Mount Greenwood: Ranks 66% safer than other communities in Chicago.
  • Westmont: Crime rate is 65% lower than the city average.
  • Rogers Park: Neighborhood is around 23% safer than the city average.
  • West Lawn: Crime rate is about 22% lower than the city’s average.
  • Streeterville: Considered very safe for being downtown, but specific statistics not provided.
  • North Center: Fewer reported crimes than many other neighborhoods in the city, but specific percentage not provided.
  • O’Hare: In 2022, there were 1,875 reported crimes, considered very safe compared to other Chicago neighborhoods.
  • Hegewisch: Only 757 reported crimes in 2022, safer than other working-class neighborhoods.
  • Lincoln Park: Crime rate is around 25% lower than in the rest of the city.
  • Printer’s Row: Very safe neighborhood, though violent crime isn’t a huge concern, property crime does occur.
  • Chicago Loop: Considered quite safe, though some violent and property crime is present.

#2 - eHarmony (Android; iOS) is one of the best Chicago dating apps for long-term relationships

eHarmony's landing page

eHarmony has been around since the beginning - and there’s a reason why: their system works! eHarmony is for those who are looking for long-term relationships in their life - they’re past the “just for fun” phase. eHarmony boasts incredible statistics such as 2+ million people finding love, 2.3 million messages sent weekly and an incredibly even pool of 51% men and 49% women.

What really sets them apart though is their success rates. 75% of all marriages that start online have begun on eHarmony and they're still going strong. If you want a "Real" relationship this is the best option for most.

Need more info on how eHarmony works for a regular guy? We’ve created an eHarmony review where you can see how the site works, how you can meet people, and how you might one day find love online!

eHarmony trial

Why eHarmony is great:

  • The success rate that no other app can touch
  • People are there for more than just fun – they want something real
  • The pool is super even – you won’t have trouble finding someone of the opposite sex
  • You get matched with those who are usually very compatible

What we don’t like about it:

  • They pick your matches for you
  • Set up process is long

What people think of eHarmony

Mickey - TrustPilot

Not bad by on line dating standards.

By dating site standards Eharmony does well. There is still the usual rejection that is a part of on line dating but it seems to be a little less on Eharmony. I think it has to do with it costs money so people take it a little more seriously when they are spending their money, LOL

Rina - TrustPilot

"I liked this app a lot.
1) Easy to use.
2) Talk to matched people without paying extra for each message.
3) Compatibility matrix is good too.
4) It's good app with real people that's for sure.

Cons :
1) Can't see all the members and their profile unless they match
2) can't share pics while chatting."


Have you tried eHarmony for dating and hookups in Chicago? If so, drop a comment below and tell us what you think!

Want to learn more about eHarmony? Read these great BeyondAges guides:

Will eHarmony Find Your Perfect Match?

Tom Senkus, Dating Expert

eHarmony’s ratio of men to women is just as you’d expect on safer apps like Bumble. While still male-heavy (like all male-female dating apps), eHarmony does not typically disclose its exact male-to-female ratio publicly, and the ratio may also change over time as new users join the platform. However, the latest stats from Statista Consumer Insights place eHarmony near the top with 51 million users worldwide

How Much eHarmony Costs: The Ultimate Pricing Guide

Sam Bradshaw, Dating Coach

eHarmony is different from most apps, as you won’t be swiping among randoms and hoping for the best. Instead, the Compatability Quiz ensures that you’ll only be matched with those who shares your interests, meet your standards, and live within a reasonable distance.

The Best Website Profile Creation Guide for eHarmony

Scott Mahoney

Do yourself a favor and take a little time to answer these questions honestly. It will pay off in the long run. If you do get impatient and click really fast you will get a popup that stops you anyways! Since there are so many questions being asked I am only going to go over the ones that require a little thought. They became known as the best website for data-driven stats for a reason!

#3 - Zoosk is one of our favorite dating apps in Chicago (Android; iOS)

Android Zoosk

If you’re tired of hookup apps like Tinder, try Zoosk instead. Zoosk is a paid dating app, so users that are on it end to be more serious about making genuine connections. There are plenty of people looking for long-term relationships, but you can also find hookups on Zoosk if that’s what you’re after.

It’s a popular app among young singles, typically aged 18 to early 20s, and there are over 35 million users on it, so it’s a great place to connect with Chicago locals. Swipe through profiles yourself to find a match or receive daily match recommendations from Zoosk.

Why Zoosk is worth trying:

  • Use the SmartPick feature to receive match recommendations
  • Good balance between men and women users
  • Easily access Zoosk via desktop or their mobile app

What we don’t like about it:

  • Free features are limited
  • Match recommendations may not be based on compatibility

Jennifer T - SiteJabber

My time to thrive

I met a man on site who supports me and allows me to grow as a person. He listens and thoughtfully answers my questions.


Is Zoosk Safe? An overview of the 2020 Data Breach

The 2020 data breach of Zoosk serves as a stark reminder of the potential risks associated with using online platforms, particularly those involving sensitive personal information. In this significant cyber-attack, the personal data of approximately 30 million users was compromised. This breach occurred around January 12, 2020, when an unauthorized third party gained access to Zoosk's data stored in a third-party database. The severity of this breach was further underscored by the involvement of more than 200 million user records across at least 13 companies.

The responsibility for this security breach was claimed by a hacking group known as "ShinyHunters," who attempted to sell the stolen data on a dark web marketplace. The nature of the compromised data in such breaches typically includes email addresses, passwords, personal preferences, and possibly financial information, although the specific details of the compromised data in this incident were not fully disclosed.

Following the breach, Zoosk faced criticism for its delayed response, reportedly taking 22 days to notify its users of the incident. This delay potentially increased the risk of harm to affected users. Consequently, Zoosk and its parent company were subjected to a class-action lawsuit, highlighting the legal and ethical responsibilities of online services to protect user data.

For users of Zoosk and similar online dating apps, this incident underscores the importance of exercising caution and staying vigilant about personal data security. It's crucial to use strong, unique passwords for each online service and to be cautious about the amount and nature of personal information shared on these platforms. Users should also stay informed about the security measures and privacy policies of the services they use, and remain alert for any unusual activity in their accounts or suspicious communications that could indicate a data breach. This event is a reminder of the ever-present cyber risks in the digital world and the need for continuous vigilance in safeguarding personal information.

#4 - BLK (Android; iOS) is one of the best dating apps for black singles

BLK on Android

BLK is a vibrant and user-friendly dating app specifically designed for the Black community, making it a perfect match for people looking for the top dating apps in Chicago. With the city boasting a substantial Black population – nearly one-third of its residents – BLK offers a tailored platform where African American singles can connect based on shared experiences, cultural backgrounds, and interests. This app stands out in Chicago's diverse dating scene by providing an exclusive and safe space that celebrates and prioritizes Black love and relationships.

What makes BLK particularly appealing in a bustling metropolis like Chicago is its emphasis on simplicity and ease of use. The app's intuitive design allows users to swiftly set up profiles, navigate through potential matches, and initiate conversations. This straightforward approach is ideal for those who are new to online dating or prefer a more streamlined experience. Whether you're a Chicago local or new to the city, BLK offers a welcoming and inclusive community where you can find meaningful connections, from casual dates to long-term relationships.

Why BLK is an awesome dating app:

  • Exclusive dating pool of black singles
  • Black singles may not feel as fetishized as they do on other apps
  • Super user-friendly app

Why you might want to use another app:

  • If you’re not black, this isn’t the app for you
  • There are a lot of fake profiles

What people think of BLK

Kvsandy - App Store

 “I met my life partner on this app

What more can I say, I was able to have interesting conversations with individuals I would likely never have encountered irl. I met the love of my life and ultimately deleted the app. Feedback I got from men though, was that apparently they’ve been having a tough time with discerning if a person was on there to meet people or boost their various online profiles. (You know which kind I’m talking about). My profile was sort of cryptic, to be fair. On occasion this prompted men to aggressively try to attain my socials. I think asking users to answer a few basic compatibility questions in their profile might offset this. The app also regularly reminded me that I had downloaded it which encouraged me to use it and respond to messages and new matches more often. I enjoyed the cute and sometimes cheesy reminders about how I was breaking hearts and to not keep my matches waiting. I don’t have any complaints really, because I met someone that I love deeply so everything feels all rosy now. I am a conventionally attractive, well read, socially conscious, 30 something - so I’ve never had trouble meeting people in real life, I merely wanted to fish from a lake or faster moving river as opposed to a small pond.



#5 - Bumble (Android; iOS) lets you buzz around for dates

Bumble features

Bumble is fast, easy to set up and extremely user-friendly. It’s for those who are casually looking for a date and maybe want to have some fun. They’ve also added a few new cool features being Bumble Bizz (for networking and professional development) and Bumble BFF (for finding friends in your area). If it’s not the best Chicago dating app for dating, then it might be the best one for meeting new people!

Women also HAVE to make the first move. So if you’re tired of receiving brash messages, or as a guy, you’re tired of being ghosted, this is the place to be.

Why it’s one of the best dating apps in Chicago:

  • Women make the first move
  • It’s super simple
  • It’s very casual. If you’re looking for some fun, get on Bumble!

What we don’t love about it:

  • Women message first (some things can be good and bad)
  • If your match doesn’t message you in 24 hours, you’ll be unmatched
  • There’s a decent amount of fake profiles

What people think of Bumble

H Tien - TrustPilot

Interesting experience

After a few friends recommended me to try dating apps, I decided to give Bumble a go with a premium subscription. As a female user, I had 20+ matches every day but only a handful of them turned into friend and romantic dates. I found it very time-consuming to sift through all the likes because 90% of the men didn't bother to read my profile. I only tested Bumble for five days to try the online dating experience, but I realised that it wasn't for me. I prefer to meet people face-to-face through speed dating events for potential dates.


Bumble Guides from Bumble!

At BeyondAges, we believe in giving you the most objective information you’ll find, and it’s great to hear how to use an the platform directly from the creators of the app and website.

One of the best things about Bumble is that they offer a wealth of Bumble-centric guides on finding success with the app AND your love life. 

For example, do yourself a favor and read “About to Go on Date Number Two? Here Are Some Expert-Approved Second Date Tips” by Bumble staff writer Ali Drucker. In this guide, Drucker includes expert advice from a number of industry professionals. Here’s just a few excerpts:

  • Sexologist psychotherapist Dr. Kristie Overstreet: “You have to tell yourself, ‘I’m just going to be me. And I would rather know sooner than later if they can’t handle me being 100 percent myself’. … You owe it to them to do the same thing.”
  • Sex therapist Dr. Lexx Brown-James: “Directly asking for consent in [common] circumstances might seem a little corny,” but it’s “really helpful for easing into trust with one another.”

#6 - Tinder (Android; iOS) is the app that everyone knows

Tinder Android features

Tinder is a staple of the casual dating industry. They were the O.G.’s for implementing the swiping feature. Almost every person I know who happens to be single uses Tinder - almost on a daily basis. It can be addicting, but that’s because it always gives you results. Their algorithms consistently place matches in front of you, which align with your preferences. No doubt, it’s one of the best dating apps in Chicago for those who want to venture into the world of online dating.

Why Tinder is great:

  • It’s super simple
  • It has an absolutely massive dating pool
  • There are much fewer fake profiles in comparison to other apps

What we don’t like about it:

  • It’s mainly for casual dating
  • Without paying, it can be quite lackluster

What people think of Tinder

Anjinah Akhi - TrustPilot

So many bad experiences but i eventually met the love of my life here


What’s in Tinder’s Terms of Service? Stuff You Should Know

Let’s be honest: Not everyone has the time to read Tinder’s fine print. To do you a favor, we’ve skimmed Tinder’s Terms of Service to find about anything that might affect you in a number of scenarios. Here’s a breakdown of potential risks you may face using Tinder:

Category Potential Risks
In-App Purchases and Subscriptions Users might incur unexpected fees through in-app purchases and auto-renewal subscriptions.
Payment Method and Billing Providing payment details could lead to risks if Tinder's security is compromised. Tinder may correct billing errors, potentially leading to unexpected charges.
Interactions with Other Members No background checks on members could result in interactions with potentially dangerous individuals. Sharing personal or financial information could lead to cybersecurity risks and personal safety threats.
Third-Party Services and Links Links to other websites or resources could expose users to different terms and risks not covered by Tinder’s security measures.
Account Security Users are responsible for the security of their login credentials. Compromise of these credentials could lead to unauthorized account access and potential misuse.
Content Rights and Privacy Users’ content, including personal data, is accessible to Tinder, posing privacy risks if misused or in case of a data breach.
Virtual Items Purchases of virtual items are final and non-refundable, potentially leading to unintended expenses.
Dispute Resolution Mandatory arbitration and waiver of class action lawsuits limit users' options in resolving disputes, potentially involving financial claims.
Indemnification Clause Users agree to indemnify Tinder against claims, which could involve legal fees or other costs if the user's actions lead to legal proceedings.

#7 - DOWN (Android; iOS) is for flings

Screenshots of Down app

Down was made with one goal in mind for its users: to get some action. Down is specifically designed to find you casual flings in your area. If you really don’t want something serious - this is the app to download. They have a “date” section but it is used much less often. They also keep those you like completely in the dark, unless both of you happen to like one another; then, it’s off to the races (racing to the bed, that is)!

Why DOWN is great:

  • It’s great for fast and fun hookups
  • The app is quickly growing
  • There’s also a dating section if you so please

What we don’t like about it:

  • Although the userbase is growing, it is still quite small
  • You’re very unlikely to find anything serious here

What people think of DOWN

alice n. - SiteJabber

Awesome app for hookups

Compared with Lucky, down is another great hookup app. Had tried for 2 months and did not get lucky.



#8 - Tastebuds (iOS) is for music lovers

Tastebuds features

Tastebuds is such a unique app - if you’re really into music, there isn’t a better dating platform to be on. What Tastebuds does is it allows you to match with those who share a very similar liking in terms of music. It’s undoubtedly one of the best dating apps in Chicago for those who take their Spotify playlist seriously.

Imagine you’re in the car, driving back from your amazing date and you throw on some Drake; your date goes “Ew, I only listen to Katy Perry!” Yeah, that probably wouldn’t work out too well, would it? With Tastebuds, you can guarantee that won’t happen. By focusing on music preferences, Tastebuds creates a harmonious dating environment, especially in a city like Chicago where music genres are as diverse as its neighborhoods. It's not just about finding a date; it's about finding a concert buddy, a vinyl record-shopping partner, or someone who understands your love for jazz or house music. In essence, Tastebuds isn't just a dating app, it's a gateway to connecting with someone who not only matches your romantic interests but also grooves to the same beat as you do.

Why Tastebuds is among the best Chicago dating apps:

  • If you love music, this is the place to be
  • The app is super slick and easily navigable
  • Tastebuds’ user-base is growing extremely quickly – find a match easily

What we don’t like about it:

  • It’s only available on iOS
  • If you’re not super into music, Tastebuds probably won’t be for you

What people think of Tastebuds

Hergy F. - SiteJabber

Poor website, no money invested

Whilst the idea is a good one, the people behind tastebuds are clearly not very technical when it comes to websites and software.

The website functions poorly on mobile, running slow and constantly freezing. There is no android app available either.

This could have been a brilliant site, but it has suffered due to the lack of technical know-how from its creators. Such a waste.


#9 - Inner Circle (Android; iOS) is one of the best dating sites in Chicago

Inner Circle on iOS

Inner Circle has created a user base of serious singles looking to meet their other half. The app encourages users to have meaningful conversations by offering pre-built conversation starters, member nights/events, and date idea sections for your profile. All of this allows for a smoother transition into actually meeting the person. If you’re looking for something more serious but also simple, hop on Inner Circle.

This app stands out by focusing on facilitating real-life connections, making it a great choice for those who are tired of endless swiping and superficial chats. Inner Circle carefully curates its community through a detailed screening process, ensuring that your potential matches are genuine and equally interested in a meaningful relationship. Plus, with its unique feature of organizing exclusive member events, Inner Circle offers a dynamic way to meet interesting people in a relaxed, social setting, perfect for those who value in-person chemistry. Whether you're seeking a long-term relationship or genuine connections in a casual dating landscape, Inner Circle provides a platform that aligns with your intentions.

Why Inner Circle is great:

  • It’s for more serious singles
  • It gets you out of the app and into the world
  • It’s still very user friendly

Why we don’t consider it the best dating site in Chicago:

  • You have to pay in order for it to be worth it
  • Confusing payment structure for chatting

What people think of Inner Circle

David Field - TrustPilot

App is working fine

I came back to edit this review. They accepted my profile, finally and it seems to be working but I will leave it at 4 stars because of what others said about fake profiles and the deleted Google review. I might change it to 5 if I have a different experience than others.



#10 -  heybaby (iOS) is for parents or those who want children

Heybaby iOS features

heybaby was designed for parents or those who want to have kids in the near future. As you’d probably assume, the user base consists mainly of people older than their mid-20s. That’s not a bad thing though - this setup allows you to get through a lot of “meh” matches and only be presented with those that actually would work. The signup process isn’t mundane either; in fact, the entire process is a lot of fun!

Why heybaby is great:

  • It’s unique to those who have or want children
  • It’s a fun sign-up process
  • It’s serious enough to find a lifelong partner
  • It’s one of the best dating sites in Chicago for single parents

What we don’t like about it:

  • It’s only on iOS
  • There isn’t a massive amount of users

What people think of heybaby

Zyngaf116 - App Store

Easy to Use

My first impression of the app was the choice of colors/graphics. It has an inviting feel (red is the color of love) so that captured my attention right away. I didn’t feel bombarded with questions from the beginning like some other apps,. The questions were fun, quick, and simple due to the preloaded answers without the need to think of something clever on my own.

The app was simple to use up until I had to upload pics, I went back to change one, however the app made me upload all the pics again. It would be helpful to have an option to edit just one pic. Other than that, the app was smooth and seamless to navigate. I was just confused on the number system for potential matches. I feel like the explanation was vague and I was still left wondering what it means? The higher the number, the better the match? The verification process was also simple and straightforward and a nice touch for me to feel safe from cat-fishers. Overall, Heybaby was the fastest profile creation I’ve done on a dating app.

I would recommend my single friends to this app who are serious daters. It definitely seems like a place to connect with individuals who have or want kids or at least open to the kid/future conversations.


#10 - LOLO (Android; iOS) is one of the BEST dating apps in Chicago

XO screenshots

LOLO isn’t your typical dating app. Yes, you find matches. Yes, you talk with them in-app. And yes, there are likes/dislikes or swipe right/swipe left; but there’s one big thing that makes all of these features WAY more interesting. LOLO uses games as a way to allow the conversation to flow much, much more freely. Tired of texting without any substance? Texting without knowing what to talk about? LOLO allows for this “awkwardness” to be completely surpassed - you can now talk about the game you two are playing (and how you’re whooping them, hopefully).

By incorporating interactive games, LOLO transforms the dating experience into a fun, engaging journey, where you get to know someone through playful competition and shared interests. It's a fresh take on breaking the ice, as these games provide a natural topic of conversation, taking the pressure off those initial awkward chats. Additionally, the way you play can reveal a lot about your personality and sense of humor, giving both of you a deeper insight into each other's character. With LOLO, you're not just looking at a profile; you're actively engaging in a shared activity, making the connection feel more organic and enjoyable. So if you're someone who loves a bit of friendly competition and wants to skip the small talk, LOLO might just be your perfect match-making playground.

Why LOLO is great:

  • The game feature makes it unique
  • You have fun with your match right from the get-go
  • There’s a blind-game option (you play a game and talk with a person before seeing their profile)

What we don’t like about it

  • It can be very casual, removing some good tension
  • Competitiveness can get in the way

What people think of LOLO

Official Meshay - Google Play

Good idea to play games to take the pressure off of starting a conversation. The distance feature isn't great as matches in games can be across the country. Messages from different people can wind up in separate games which is distracting. It doesn't always load correctly, so I have to close the app completely and reopen it. That's a minor inconvenience though. The push notifications don't open the app for some reason. I mean, it's cute though. Lol



A long-term couple in a park

The Best Dating Sites in Chicago for Long-Term Relationships

Knowing what you’re looking for can help you find the perfect dating app. To help you out, we’re going to spotlight some of our favorite dating apps for people looking for long-term relationships. Here are two of our favorites:

eHarmony is the best Chicago dating site to find a relationship

eHarmony is one of the most well-known dating sites on the market because it’s been around since 2000. The site has such a good reputation because it has helped over 600,000 people in America alone find love and get married, making it the perfect place for people to find long-term relationships.

eHarmony’s success is likely due to the detailed questionnaire about users’ preferences in a partner, interests and lifestyle that everyone must complete when they sign up. eHarmony uses people’s answers to match them with users based on their compatibility. This makes it easier to find common ground and start chatting.

Bumble lets women take control of their dating lives

Bumble has become increasingly more popular among women in Chicago who are looking to settle down. The appeal of the app is that women must make the first move within 24 hours of matching. Otherwise, the match disappears. This allows women to control who can message them and encourages them to actually reach out and start a conversation rather than just having matches remain stagnant.


Waiting for a hookup date she met online

The Best Hookup Sites in Chicago

We know that not all singles are looking for something serious on dating apps, so we’re also going to spotlight some great casual dating apps. Here are two of our favorite Chicago hookup sites:

AFF is one of the best casual dating sites in Chicago

AFF is the opposite of eHarmony, though it's just as effective. Instead of helping people find true love, it helps people find hookups. As it’s advertised as a hookup site, there’s no confusion about what people are looking for on there. This takes away the need for that awkward conversation about your intentions.

With over 60 million users on the site, we’re sure you won’t struggle to find a single hottie in your area. You can match with people by location or filter your searches further based on things like age, body type, or other preferences.

Tinder has quickly become the best free hookup site in Chicago. Although it’s not advertised as such, it’s what most people use the app for. This is because Tinder is so easy to use that it makes matching with people feel like a game. Though keep in mind that the app is also very focused on looks, so people are usually just looking for someone hot to hook up with.


Meeting new people on a free dating app

The Best Free Dating Sites in Chicago

Have you ever heard the saying, “You get what you pay for?” Well, it’s true, especially when it comes to dating apps. Free dating apps and sites are fun to use but they typically don’t offer the same results that paid ones do.

Paid memberships give you access to features that can help improve your chances of finding true love or a really good hookup. We know plenty of singles, ourselves included, that have had much better luck after paying for a dating membership, so it’s definitely an investment in your future.

If you’re not ready to pay for a membership just yet, take advantage of a free trial or app instead. This lets you test the waters so you can figure out what you like or don’t like in a dating app. Just don’t expect crazy results with the free versions.

Here are three of the best free dating sites in Chicago:

  • OkCupid
  • Hinge
  • Tinder

All three apps are free and easy to use and you can pay for additional features to help you find more success.

Safety & Precautions: Avoiding Online Scams in Chicago Dating Apps

In the digital quest for love, users of Chicago dating apps must be vigilant against romance scams, also known as catfishing. The FBI has outlined several tips to help avoid falling victim to these scams:

Advice Description
Be Prudent with Personal Information Limit what you share online to prevent scammers from using personal details against you.
Verify Identities Use online searches to check if names, photos, or details have been used elsewhere or in scams.
Proceed with Caution Move slowly and ask questions to avoid being swept up in false narratives.
Stay Connected to Your Network Beware of attempts to isolate you from friends and family.
Never Send Money Do not send money or share financial information with someone you haven't met in person.
Meet Safely and Publicly Arrange meetings in public spaces and inform someone of your plans.

By understanding and implementing these safety measures, individuals can better navigate the complex and sometimes perilous landscape of online dating. Always prioritize personal safety and emotional well-being, remaining vigilant against the sophisticated tactics of online scammers.

FAQ about Chicago Dating Apps and Sites

Tinder may be popular, but when it comes to effectiveness at finding a date, eHarmony beats them all.

Yes, Tinder is popular. But if you want to hook up, AFF is a better option. For relationships, eHarmony is much better.

How do I meet singles in Chicago?

Using dating apps like eHarmony, AFF, and Zoosk are fantastic ways to meet Chicago singles.

Is dating easy in Chicago?

The easiest way to find a date in Chicago is by using high-quality dating apps like eHarmony, AFF, and Zoosk.

In Chicago, popular dating apps include Tinder, Bumble, Hinge, and OkCupid, each offering different experiences and catering to various preferences.

How Can I Choose the Best Dating App for My Needs in Chicago?

Consider your dating goals, whether you're seeking casual encounters or serious relationships, and check out user reviews to determine which app aligns with your preferences in Chicago.

Are There Chicago-specific Dating Apps or Features?

Some dating apps offer location-specific features that cater to Chicago's unique urban landscape and cultural scene, enhancing the local dating experience.

What Safety Precautions Should I Take When Using Dating Apps in Chicago?

Always meet in public places, inform a friend or family member about your date plans, and trust your instincts when interacting with matches.

What Are Some Great First Date Ideas in Chicago?

Chicago offers diverse date options like exploring Millennium Park, enjoying the city's vibrant food scene, visiting museums, or taking a walk along the Lakefront Trail.

How Do I Navigate Dating in Such a Diverse City as Chicago?

Be open to meeting people from different backgrounds, show interest in learning about their experiences, and embrace the diverse dating opportunities Chicago offers.

Is Online Dating in Chicago Effective for Finding Long-term Relationships?

Many people in Chicago successfully find long-term relationships through dating apps, especially those apps designed for more serious connections.

How Should I Present Myself on a Dating App Profile in Chicago?

Use recent and clear photos, write an honest and engaging bio, and highlight your interests and what you love about living in Chicago.

How Can I Balance Online and Real-Life Dating in Chicago?

Stay active on dating apps but also take advantage of Chicago's social events, clubs, and activities to meet people in person.

What Are the Differences Between Free and Paid Dating Apps in Chicago?

Free dating apps are accessible to a broader audience but might include more casual users. Paid apps often provide more advanced features and attract users more serious about dating.

How Should I Respond to Ghosting on Chicago Dating Apps?

Understand that ghosting is a part of online dating, don't take it personally, and focus on matches who show genuine interest and communication.

Are There Etiquette Tips Specific to Dating in Chicago?

Respect the city's diversity, be clear about your dating intentions, and consider the local norms and preferences of Chicagoans.

What's the Best Way to Transition from Online Chat to an Actual Date in Chicago?

After establishing mutual interest, suggest a public meeting place that reflects shared interests, and choose a relaxed activity for your first date.

Can I Find Both Casual and Serious Relationships on Chicago Dating Apps?

Yes, Chicago's dynamic dating scene caters to a variety of relationship goals, from casual encounters to serious partnerships, depending on the app you use.


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Contributing Authors:

Tom Senkus

For more than two decades, Tom has dated extensively and studied behavioral psychology as a way of understanding the complexities of human nature until he became an expert. After traveling as a touring musician and living in more than 15 countries, Tom has cross-referenced his experience in seduction, dating, and interpersonal dynamics with the ever-changing landscape of 21st-century dating. His work as a writer has appeared in 500+ publications (digital and print). Tom is also the author of several books (available on Amazon). In his free time, you can find Tom recording music and cooking the best Cincinnati-style chili you’ve ever had.

Sam Bradshaw

One of the founding members of Modern Love Systems, Sam has been coaching his friends to better dating success since he was in his teenage years. After graduating from university he began working with other men struggling with their dating lives eventually founding Modern Love Systems to help even more guys. With over a decade of professional experience, Sam is the mastermind behind our systematic approach to dating online.

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