Dating in Chicago, Illinois (IL): Resource Guide for 2023

Interested in dating in Chicago, Illinois? This gorgeous, iconic major USA city was the birthplace for Walt Disney and a playground for Al Capone, the hot-shop gang leader that ruled Chicago through the early 1900s! The land of Chicago holds plenty of promise and adventure for hopeful singles looking to date and the story-rich streets and historical building provide an excellent environment to let love blossom.

In Chicago, you’re surrounded by everything you need for a first date all the way to the last. Over 5,195 restaurants, 20 neighborhood art centers, 250 theaters, and 580 parks and 26 beaches make the whole city ideal for adventure and exploration. It’s a city of bustling life, that much is a promise, so you’ll never be bored while hunting down a perfect partner in Chicago.

Best Chicago Dating Sites

For Singles: is the best for dating in Chicago Illinois

As the most notable dating site online, Match holds the standard for everyone else to follow. It’s the most successful dating site out there, resulting in the most marriages that happen from their services. Chicago singles fill out a large portion of the multi-million user base and there is tons of ways to discover, interact, and meet Chicago residents looking for love online. Unique features and a 100% match guarantee promises a match within 6 months, or an additional 6 months free!

The site is only available to those who purchase a membership, but the tiered payment plans are affordable and easy. Probably as cheap as any one speed dating event in a city like Chicago, notorious for it’s high-profile pricing. Purchase one, three, or six month memberships that include discounts or deals and unlocks the full dating potential of

For Professionals: Elite Singles

elitesingles review

If you’ve ever used a dating app before, you probably know the routine… and the common type of singles you’ll meet there. Not everyone is interested in just general, casual dating online – and that’s fine! For a professional who cares a lot about their career and educational history, you need a much more form-fitting platform to enjoy and explore. Elite Singles is host to thousands of Chicago-based online daters with college degrees and successful careers, looking for others who understand the importance of progression and can handle a busy schedule.

The site curates matches for you and sends you a batch daily. Choose from the batch, or wait 24 hours for a refresh. Each one is selected for your personals preferences, and the paid membership that is required is very affordable. If you’re a professional single 30+ in Chicago, this site is for you.

For Seniors over Age 50: OurTime

our time in Chicago Illinois

Finding love seems to get harder the older you get. For 50+ Chicago singles, you’re probably well aware of the tasking journey it takes to find real connections. It’s a big city full of youngsters, but OurTime is a special dating service online designed to bring seniors in Chicago together hassle-free. Email and write with other single seniors near you, and maybe even meet in person if you choose!

Paying for the OurTime membership is simple. Choose from 1-6 months worth of unlimited access and start chatting! Plenty of great partnerships with Chicago seniors are made right on the platform.

For Gay/Lesbian:

It’s no surprise that Match gets yet another shout-out here! For online dating in 2019, Match has been ranked #1 with gay men and their lesbian and bisexual population is growing daily. Elite Singles and Zoosk followed closely behind Match, providing inclusive safe dating spaces for gay men and women in Chicago. Finding a dating app with LGBTQ+ acceptance is vital to modern dating, so is a great, solid option to meet anyone.

For Hookups: Adult Friend Finder

So, not into a relationship, huh? A lot of busy Chicago partiers aren’t, either! We all want someone to admire and experience for a night in, and Adult Friend Finder was designed for just that. Chicago is full of frisky singles who don’t want to commit and just want an exciting night. Connect with someone on the site, meet up for a beer, and take them home that very night. Really, it’s that easy!

Best Dating Apps in Chicago

Dating in Chicago is great when done online, but even better if you go mobile with your matching. Using your phone to connect on-the-go is the best way to take advantage of the Chicago dating scene online, so give one of these two apps a try!


Get instant, unlimited access to over 40 millions members, tons of them right there in Chicago, in a few simple steps. This app is the top-rated on app stores for any device, and has the easiest sign-up experience ever. Plus, it’s basically free, unless you want additional add-on features to increase success. Swipe through potential matches, text back and forth, and start dating in Chicago from anywhere with just your cell.

Plenty of Fish

Like Zoosk, PoF has a massive membership count and tons of hits daily. With offered chat rooms, personals, and instant messaging, you can meet hundreds of Chicago singles at any hour of the day. Unique matching methods bring tons of different types of people you may enjoy right to your cellphone’s screen, and it’s quicker and easier than anything else out there.

Best Dating Bars for Singles in Chicago

Catching a drink during a night out on the town is one of the best ways, if not the #1, to snag a date in real life, or take someone you’ve met online for a first-time meet-up. Chicago city is full of bars, nightclubs, and exciting places where hopeful singles of all ages like to join together and hang out.

If you’re flying solo or with someone on your arm, one of these 3 bars is a great destination for a wonderful evening of flirting and romancing. Chicago is a crazy city, but take a breather and slow down with a hopeful partner to get to know the residents better!

Twisted Hippo

This brand-new bar on the Chicago dating scene is trendy, fabulous, affordable, and crazy popular in 2019! With bright hot pink and neon lime green, the bar stands out in a great way, and they provide excellent service with full menus and 14 beers on tap. Plus, there is no reason to bring extra money for tipping, because The Twisted Hippo includes fair wages for their servers and bartenders in the base price! Their all-inclusive motto is “what you see is what you get”, so you can easily plan ahead and budget.

King of Cups

Chicago’s own royalty themed bar King of Cups is a high-class, affordable way to spend a night in luxury. Plush seating, themed original cocktails like the Smerch’s Swizzle and tarot card readings every day. Catch live music and dancing on Saturdays, or go any day of the week to enjoy the mood-lit plush seating and delicious menus and fun partiers. This mystical lounge is a totally new experience to driving, so date like a royal every once in awhile at King of Cups.

Hyde Speakeasy

Not everyone will appreciate the specific mood of the Hyde Speakeasy bar, but if you want a truly Chicago experience and a flashback to the 20s, it’s a must-see at least once. Plus, so many fun singles hang-out at the crazy scene, you’ll find a few potential dates in no time! A full link of rules is posted, including funnily sarcastic quips about required behavior such as What happens in the Hyde,  stays in the Hyde. On Instagram, you can find their exclusive “password” to be granted access to their beer and full food menu – just like in the old Al Capone days of the gang wars!

Speed Dating in Chicago

The best way to tons of eligible singles quickly in a big city like Chicago without sifting through online dating services is to try out one of the speed dating groups! Introduce, flirt, get to know, and exchange numbers with plenty of people who interest you and see where it leads all at once. What’s to lose, right? Check out these speed dating clubs and events happening all around Chicago frequently:

Chicago Dating Events & Clubs

While speed dating is fun and a useful experience, it’s not everyone’s cup of tea, and that’s fine! Chicago has much more to offer in the romance department than just quick roulette dates, and there are dozens of ways to get involved with other singles all across the city. Try out one of these events or dating clubs in Chicago:

Dating Chat Rooms in Chicago

Don’t want to leave the house or spend time signing up for complicated dating apps? Got you covered, boss! Pop onto a free ‘n simple chatroom for Chicago locals looking for love at any hour of the day and chat easily with the other members signed on. Some safe ones to look at are:

Personals in Chicago

Still hungry for more options? It’s not quite as safe as dating apps or in-person connection, but looking up personal ads posted online can help you find exactly what you’re looking for easily, no registration or effort required. Chicago has plenty of sites with promising personals, but these seem to be the most scam-free out there:

Things to Know about Chicago Dating

Everything about Chicago is exciting. It’s busy and big, the best part of the tiny Illinois state, and attracts people from all over the world. From massive music venues to hundreds of theaters and live performances, renovated buildings from the 20s, and everything in between, Chicago is one of the must-visit cities in the US. This is especially true if you’re single and ready to mingle!

As diverse as it’s entertainment, Chicago locals come from everywhere and every shape, color, background, religion, or orientation. There is someone out there for everyone, but chances are, you’ll find them in Chicago.


2,707,120 people are proud to call Chicago home! In a city that is only 234 square miles big, that is a lot of people. It’s the third largest city in the US and has plenty of unique and culturally diverse residents. 2.1 million of these residents are adults, which proves Chicago is full of singles just like you.

  • White: 49.14%
  • Black or African American: 30.51%
  • Other race: 11.19%
  • Asian: 6.22%
  • Two or more races: 2.63%


Nearly 60% of Chicago locals state to be religious people. Over half of the residents have chosen a religion, and these 4 are the most common in the city:

  • 38.7% are Catholic
  • 13.9% are a Christian faith (Lutheran, Methodist, etc.)
  • 3.9% affiliated with Islam
  • 1.1% are Judaism


146,000 Chicago adults identify as somewhere on the homosexual spectrum, with over 10,000 of these people identifying as transgender. With several LGBTQ+ clubs and bars around, connecting with the huge homosexual population is really easy, and they are very welcoming and accepting of non-binary and otherwise non-cis identifying locals. Exploring LGBT Chicago can help you find the best places to search for other gay companions!

Wrap Up

Are you ready to hit the vivid Chicago streets and hop a few bars? Dating in Chicago is both an experience and a journey, but one that is well-enjoyed and memorable for life. Who knows – your soul mate could be lurking right around the next corner, or stuck in the infamously crazy Chicago traffic! Use these resources to end your single chapter and open the next.

chelsea king - chief editor of romancescams
Written by Chelsea King

Chelsea has been a direct victim of romance scams herself losing over $35,000 in a span of a year in 2015. She joined and took over operations of in 2015. She brings first-hand experience in studying romance scams, and also experience in vetting dating sites for legitimacy. Read more of Chelsea's articles.

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