How to Navigate the Chicago Dating Scene
Being a Midwestern girl, I’ve visited The Windy City at least 50 times. With each visit, I fall in love with Chicago’s iconic skyline, bustling neighborhoods, culture, and cuisine all over again. Personally, I believe Chicago is the most romantic city in the U.S. Despite its romantic charm, Chicago is also one of the worst cities to be single in.
Chicago’s dating scene can leave even the most eligible singles feeling discouraged. A study by WalletHub shows that Chicago singles have a drastically lower chance of finding a partner than singles in other major cities. In other words, 89% of Americans have a better chance of meeting someone special than Chicagoans!
And according to the Illinois Department of Public Health, the marriage rate in Illinois has dropped by over half in the past 50 years. Unfortunately, that trend doesn’t seem to be slowing down. We can’t distill why Chicago’s dating scene has deteriorated to a single issue; really, it’s more complex than that.
As shown in a recent survey by TimeOut, only 22% of dates end in a serious relationship for men, and that percentage drops significantly for women. Women who responded to the survey said that 12% of all dates lead to a partnership, which is abysmally low.
But how are so many people in The Windy City searching for love, yet can’t seem to find it? As Luxury Chicago Matchmakers, our team at LUMA recognizes the major issues with the city’s dating scene and why singles can’t catch a break. We’ll share the typical challenges singles face in the Chicago dating scene and provide some strategies to overcome these challenges and find your perfect match.
Challenges of Dating in Chicago
Yes, we’ll teach you how to master dating in Chicago, but first, it’s crucial to understand why the dating scene is so challenging to begin with. Most cities face similar issues with dating, but Chicago has a few uniquely problematic aspects, like the intense winters, that make finding love even more unattainable.
Dynamic City Lifestyle
As quoted by the new station WGN9, Chicago is one of the most stressful cities for workers in the nation. With long commutes and a demanding work culture, most Chicagoans simply don’t have time to actively date. Balancing a grueling work schedule, time with family and friends, and staying on top of household chores means that dating falls by the wayside.
With all of these things tugging at your schedule and begging for more of your time, it’s easy to see why Chicago has such a tough dating scene. Really, who wants to go out on a first date right after a 12-hour shift?
Extreme Weather
Chicago’s winters are fantastically cruel with freezing temperatures, icy winds, and devastating snowdrifts all barraging the city. As one of the more northerly U.S. cities, Chicago winters are fairly long, too, which means that for the majority of the year, outdoor dates are out of the question. The colder months of winter also brings isolation as many people refuse to get out in the weather unless absolutely necessary.
Yearly dating slumps unfortunately spell disaster for couples who don’t already live together. Because Chicago singles hide out from the cold, it’s difficult to maintain any momentum in fresh relationships. So many summer romances fizzle out when the cold of winter sets in because they don’t have time to develop.
The Neighborhood Effect
Yes, Chicago has plenty of skyscrapers, but that doesn’t mean it’s immune to the sprawl most cities face. Chicago has a vast city layout with distinct neighborhoods, which can make it feel like you’re dating in a bubble. The impact of intense traffic and tight-knit communities means that dating someone outside your neighborhood is a real burden.
The inconvenience of having to commute to your love interest creates barriers and limits on who’s actually in the dating pool. Because it’s so difficult to travel for dating, tons of Chicagoans miss out on the larger, more diverse dating pool of the city’s greater area. But really, would you want to commute 2+ hours for a date that might go no where?
Choice Overload
As listed by Statistica, the Chicago metro area boasts the 3rd largest metro population in the country, and over 9 million residents call The Windy City home. With literally millions of singles to choose from, how can anyone make a lasting connection? The overwhelming amount of options in the dating pool leads to decision paralysis and dating fatigue.
Having too many potential matches can also make the dating scene more shallow. Why would you settle for someone with any minor flaw when you could just as easily meet someone new? This mindset makes it difficult to fully invest in any one person.
Mastering the Chicago Dating Scene
Dating in Chicago is undeniably difficult and comes with a unique set of challenges, but we’ve found ways to help singles thrive in the dating scene. You just need to make dating intentional instead of an afterthought, embrace Chicago’s culture and history, and dive into your community to find love.
Make Time to Date
Even though it’s hard, set aside dedicated time to go out on dates, attend singles events, and look for love. If you’re serious about getting serious with someone, you’ll have to set firm boundaries around how much time you’re willing to devote to work, family, and friends each week so that you actually have the bandwidth to date! Try blocking off a few hours per week on your calendar for dating, and be as committed to showing up in your dating life as you do in your career.
Explore Your Neighborhood
Part of the beauty of Chicago is unique, distinct character of each neighborhood. Chicagoans take real pride in their communities, and you can leverage that to find love. If you haven’t already, getting out and exploring your own community can be a great way to meet other singles. Something as simple as becoming a regular at your local coffee shop can lead to connections, and you can bet that most people you meet there will be locals, too!
Make New Friends
Making friends is a win-win: you’ll not only have someone new to hangout with, but you can also ask your friends if they know other singles. Friends and acquaintances are one of the best ways find love as you can pool your collective social circles to expand your dating pool. And if they’re a good friend, they can give you a good reference, too! People you meet through shared connections are also going to trust you early on as you’ve been “vetted” by the mutual friend.
Attend Singles Events
Dating in Chicago might be rough, but certain groups and organizations are trying to change that. Chicago has a vibrant culture around singles events, so if you haven’t tried one yet, it could be great way to find a partner! Jigsaw Dating hosts tons of events in Chicago, so check out there upcoming events page to find something that interests you. They host mixers fun mixers like ping-pong tournaments and singles happy hour, and they usually have a few events every month!
Get Involved in The Culture
Chicago was once considered the jazz capital of the world. Although the crown has since been stolen by NYC, Chicago still has a rich jazz, blues, and funk scene. Whether you love music or are just fascinated by Chicago’s history, exploring the city’s music scene can be a great way to meet other singles. Instead of going to the next huge concert at Wintrust Arena, check out local concerts, jazz nights, and small music festivals. Music is one of the best ice-breakers, and you’re sure to have something in common with everyone at these events!
Forget Trendy Venues
Although Chicago has some of the coolest nightclubs and exclusive bars in the nation, they really aren’t you best option for meeting other singles. Nightclubs are usually crowded, stuffy, and foster hookup culture. Instead, head to your local cocktail lounge, lowkey wine bar, or hidden gem bars for a cozier, more intimate way to date. These laidback, comfortable venues usually aren’t too packed, and they tend to attract people looking for a serious relationship.
Try a New Hobby
There’s no better place to find a new hobby than Chicago. You have nearly endless options for workshops and classes in just about every niche you can think of, like cooking, photography, painting, and pottery! Taking up a hobby is a wonderful tool for self-expansion, but it’s also a fantastic way to meet other singles who share your interests.
Get Active
Chicago’s fitness community is very close-knit and full of opportunities to meet new people. If you’re a healthy, active person, getting involved in a fitness group will help you work on your physique and potentially make lasting connections. Consider joining a gym, taking a workout class, or picking up an outdoor sport like running or biking to find a partner. Fitness groups are a great way to connect with other active singles because you’re sure to have something in common with everyone.
Find a Cause and Volunteer
Few things are more fulfilling than volunteering to support a cause you’re passionate about. A more selfish reason you should get active and give back to your community is because volunteering is one of the most meaningful ways to meet singles who share your values! Chicago has countless volunteering initiatives, from food banks to animal shelters, so choose which cause matters most to you, join a group, and help your community while making new connections.
Consider Luxury Matchmaking
If you’re tired of the stress, uncertainty, and burden of modern dating in Chicago, luxury Matchmaking offers an easier way to find love. Most Matchmaking firms are selective about who they take on as clients, meaning that you’ll only be matched with successful, discerning singles who want a long-term relationship. Luxury Matchmaking is, well, a luxury, and that’s reflected in the price, so if you’re working with a tight budget, consider joining a small local firm instead of a nationwide Matchmaker.
Ready For a Better Way to Date in Chicago?
Looking for love in The Windy City is undeniably difficult, but it doesn’t have to be so time-consuming and daunting. At LUMA, our professional Matchmakers are dedicated to getting to know you on a personal level to hand-select your most compatible matches. Our Matchmaking services are 100% confidential, exclusive, and designed to help you find real, lasting love, not just another casual fling.
LUMA is ready to make your dating life easier, stress-free, and meaningful. Complete your LUMA profile and schedule a call with our team today to start your LUMA Love Story.
