Several family members and close friends of mine have been to Chicago, and I was always super jealous of their trips. They’ve been to Wrigley Field, Lollapalooza, Millennium Park, Navy Pier, Stephanie Izard and Rick Bayless’ restaurants, comedy shows, breweries — the list is forever long. I can tell it’s an amazing city just by the stories I hear. As a single myself, I can also tell by their stories that Chicago can be an amazing place to find a date or find love.
According to BestPlaces.net, more than 35% of the 2.7 million people in Chicago are single, and our experts are here offering 10 ways to help them get out there and meet new people.
Chicago Dating Sites
Online dating came about in the 1990s, and it was a taboo thing because people weren’t used to meeting that way. They’d usually met through friends, family, and co-workers, through personal ads in the newspaper, or while out and about. Today, though, online dating is the number one way for singles to come together because it’s easy, quick, and works wonderfully. Below are some of our top choices for Chicago singles.
Best Singles Site
For the best overall online dating experience, it’s got to be Match. You’ve probably heard that Match is responsible for the most romantic connections of any dating site around, and it’s for good reason. It’s the most established, having been founded in 1995, it’s one of the largest with 30 million members, and it has all the features you need to find a match, including filters that allow you to search by location (e.g., city and even mile range).
- Relationships: Friends, Dates, and Relationships
- Match System: Browse by zip, age, appearance, more
- Our Experts Say: Match has facilitated the most dates and relationships of any dating site, and its large audience and high success rate make it our top review. Our Review »
- Browse Free: View Photos Now
Over 50 & Senior Site
Most of us are looking for someone who’s at a similar place in life, and our go-to recommendation for mature singles who feel this way is OurTime. The site is dedicated to men and women who are at least 50 years old and who want friendship, dates, or a relationship. OurTime has one of the simplest signup, browsing, and messaging processes as well, so you can still pick up on it even if you’re not the most tech-savvy person.
- Relationships: Dates and Relationships
- Match System: Search by profiles by zip and more
- Our Experts Say: OurTime is well-known in the over-50 dating crowd, particularly because it has a ton of helpful search features and an easy layout. Our Review »
- Browse Free: View Photos Now
For Black Men & Women Only
As you can tell by the name, BlackPeopleMeet is a dating site meant for black and biracial singles, and it’s a popular one at that. More than 1.4 million people visit the site every month, and new members can create a profile, add photos, search for and receive matches, and communicate (sending virtual winks, liking members, adding people to their Favorite list, etc.) without having to pay anything.
- Relationships: Deep Relationships or Just Casual Dates
- Match System: Search by location, age, more
- Our Experts Say: BlackPeopleMeet.com is the one of the largest and most popular dating sites for black and biracial singles, and the site is used by more than 5 million people a month. Our Review »
- Browse Free: View Photos Now
Hookup & Sex Site
It’s no secret that some people just want to hook up, and that’s why Adult Friend Finder was created. At 77 million members and growing, this is the largest online sex and swingers community, and the site will show you how many people in your area are logged in at the same time. Once someone catches your eye, you can get to know each other via email, video, audio, and group forums, among other things.
- Relationships: Hookups Only
- Match System: Search by location, interest, more
- Our Experts Say: Make no mistake: this site isn't about making friends, it's about finding hookups and casual encounters. No adult site has a larger or more active user base of those seeking discreet fun. Our Review »
- Browse Free: View Photos Now
Popular Dating Apps
Mobile apps have totally transformed the way people date — instead of being stuck at home in front of a desktop, they can now look for compatible dates and partners anywhere in the world. A big thing with dating apps is location-based matching, so Chicago singles can narrow down the options (it’s a big city, after all) to even the exact neighborhood they prefer.
Match.com
- Relationships: Fun Dates, Serious Relationships
- Match System: Browse by location, age, interest, and more
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About the App:
Available via the App Store and Google Play, Match is a fantastic app for dates and relationships. With a user base of 30 million singles, Match is where you’ll have a high chance of success. It’s free to download, create a profile, search for date prospects, and receive compatible matches based on personalized preferences. Free members can also chat with select members and send unlimited likes.
- Browse Free: View Photos Now
eharmony
- Relationships: Long-Term Relationships, Marriages
- Match System: Get daily match suggestions
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About the App:
Responsible for 4% of marriages in the U.S., eharmony is among our top picks for relationship-minded heterosexual singles. To become a member, add the app to your phone (iOS or Android) and then take its 29 Dimensions® of Compatibility Matching Quiz. It’s absolutely free to do both these things — as well as receive matches and communicate during other special events.
- Browse Free: View Photos Now
OurTime.com
- Relationships: Dating and Relationships
- Match System: Search by age as well as zip, gender, more
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About the App:
Made just for single seniors, OurTime is one of the most well-known niche dating apps. It’s a fun and straightforward app with simple swiping features. Once two people swipe right on each other, they can communicate. For more match options, visit the ConnectMe and I’m Interested pages.
- Browse Free: View Photos Now
Chicago Singles Bars
Sometimes there’s nothing better than locking eyes with someone across a room and feeling the instant chemistry, and that’s what bars are best for. Plus, if you have your friends around, starting that conversation shouldn’t be as nerve-wracking. We kept our list of the best singles bars in Chicago to 10 to be concise, but, to be honest, we could’ve kept going and going because there were so many good choices.
Slippery Slope
"It's a party every night in Logan Square," says Slippery Slope. From draft beer to cocktails in bottles and "cheap hooch," you won't run out of libations, But perhaps what people love most about the bar is the skee ball and its cabin-themed dance floor for rocking out to DJs and live bands. Fun Fact: Andre the Giant, of "The Princess Bride" fame, was a famous patron of Slippery Slope.
The Berkshire Room
You'll find more than just straightforward gin and tonics at the Berkshire Room. This bar provides what it calls "Dealer's Choice," barrel-finished, and craft cocktails — like a 23-year-old Pappy Van Winkle bourbon and a Double Entendre that showcases the flavors of cognac, rye, gingembre, and masala. But the Berkshire Room is far from pretentious. You can also get wines by the bottle and glass, beers on tap, and snacks and desserts such as mixed nuts and salted caramels.
Headquarters Beercade
Awesome drinks? Check! Delicious food? Check! Fun games? Check! Headquarters Beercade has practically everything you could need. It doesn't matter if you're a fan of pinball, Pac Man, Galaga, Mortal Kombat, or pinball — you'll feel at home here. HQ Beercade's motto is, "Don't grow up. It's a trap," so whatever you do, don't take yourself too seriously when you're at this bar.
Innjoy
With two locations, one in Wicker Park and one in Logan Square, Innjoy offers "double the fun." The casual dining and entertainment venue is open seven days a week: Sunday 11 a.m. to 2 a.m., Monday through Friday 5 p.m. to 2 a.m., and Saturday 11 a.m. to 3 a.m. So you can pretty much get your food and drink on anytime. Innjoy says it's a genuine Chicago hangout spot that locals and visitors will both appreciate.
Punch House
"Strong, weak, bitter, sour, and sweet," Punch House hits all the right notes. Thrillist named Punch House one of the 33 Best New Bars in America, and Chicago Magazine calls its space "cozy" and "bohemian" and its drinks "quaffable originals alongside classics." Punch House also hosts numerous events throughout the year like punch making classes and Valentine's Day celebrations for singles and couples alike.
Nick's Beer Garden
When it was founded in 1977, Nick's Beer Garden was at the intersection of Halsted and Armitage, and it moved to Wicker Park in 1994. But the bar has always been a Chicago favorite. Nick's has some of the latest nights around (open until 4 a.m. Sunday through Friday and 5 a.m. Saturday) and offers pool, shuffleboard, a jukebox, and weekly karaoke dance parties. In terms of drinks, there are beers in bottles and cans and on draft specials such as a $7 Chicago Handshake (Old Style Tallboy and Malört Shot) and $1-off well cocktails.
Chicago Speed Dating
Speed dating events are great alternatives for people who don’t really like online dating or going to bars and clubs. It can also be a great tool for people who do like those things to add to their dating tool belt. Everything is organized for you — just show up to the location and tell your dates a little about yourself. And not all events are formal sit-downs. Some include icebreaker games and forms of entertainment to make everyone feel more comfortable.
Chicago Singles Events
Singles events are somewhat different than speed dating events in that anything goes — it could be a cooking class, a basketball game, a happy hour, a cruise, or a live show. Whatever your interest, you’re sure to find one that meets your needs. The one thing all of these events have in common, though, is everyone is single and looking!
Chicago Singles Clubs
Do your Saturdays consist of dancing the night away until 2 a.m. (or later)? Do you wish you could meet someone while doing that? Well, that’s what these singles clubs are for! Sometimes no words need to be said between two people — the music just takes over and they connect. No matter if your genre is pop, rock, reggae, techno, funk, disco, or anything else, Chicago has a club for you.
Chicago Chat Rooms
Perhaps one of the biggest pros of using a chat room to come together with other singles is that it often provides themed rooms (such as politics, sports, entertainment, religion, sex, or just what’s happening that day). Getting that banter going with someone should be a cinch because you know you already have a least one thing in common with them.
Chicago Personals
Personals sites are pretty comparable to dating sites — you’re basically placing an online ad about your personality, life goals, hobbies, and what you desire in someone else. We’re fans of the five personals sites below for many reasons — not only are they free and not only do they have large user bases, but they also have pages just for singles living in Chicago.
Take Part in Community Activities
A fun and meaningful way to meet singles is to get involved in the Chicago community if you aren’t already. Volunteering allows you to make a difference with others who want to do the same. For example, there’s Open Books, Howard Area Community Center, Big Brothers Big Sisters of Metropolitan Chicago, and the Night Ministry. Or search for “Chicago volunteer” on Google to see what you find.
Volunteering is a fantastic opportunity to do something nice for Chicago while also getting to know other philanthropic people.
What about taking an adult class with people who also want to learn something new? We’ve seen all kinds of options, including Botanical Drawing at the Chicago Botanic Garden, Intro to Swing through Big City Swing, and Beginning Italian via Casa Italia.
If You're Religious or Spiritual, Attend Worship Services
Religion or spirituality are common qualifiers singles don’t want to budge on, and it makes sense, especially if they’re commitment-minded. They want someone who’s on the same page and can spend their life and raise children with. Chicago is a city rich with religious and spiritual opportunities. Some of the top suggestions we’ve seen are the Zen Buddhist Temple, the Unity Church in Chicago, ISKCON Chicago, and the Sivananda Yoga Vedanta Center. But you should definitely do some research of your own to see which place is the best fit for you.
Chicago Singles, Get Ready to Mingle!
Chicago is definitely on my bucket list of cities to visit, and I can’t wait to one day share my own stories with my family and friends (or rub my Chicago stories in their faces, however you want to put it). If you’re a single in Chicago, you should know how lucky you are to live in such an awesome place. There’s always something to do and someone to meet, and we’ve showcased some of the best ways to do so in this article. Good luck!
Photo sources: heislerhospitality.com, danblackman.com, chicagoreader.com, zagat.com, towntalk.co.uk, chicagonow.com, bbbschgo.org
