How to Succeed Dating in Chicago in 2022 According To Dating Experts

Couple on a date night in Chicago by the river walk

Dating in Chicago is daunting, and it doesn't get any easier out in the suburbs. We're spoiled for choice here with so many singles but meeting new people and having successful dates can be really tough even post-pandemic.

The good news is that with a little effort on your part, finding a date in Chicago is easier than in most cities. You just might need to leave your neighborhood every once in a while to make it happen. Taking a bus to a bar doesn't exactly sound like the start of a great romance but you'd be surprised!

In this guide, we're going to give you some proven suggestions on where to meet Chicago singles, great date ideas, and some of our favorite date spots around Chicago that have been the location of some pretty incredible dates. First, let's set some expectations about what the dating scene is like:

The percentage of singles in Chicago by gender

What dating in Chicago is like right now

The dating scene in Chicago has always been pretty turbulent and the pandemic made things worse. There is a constant in-flow and eventual exit of singles into the city (often fellow mid-westerners that live here from 22-30 and then go back to Michigan or Iowa) but that's pretty typical of any big city. With so many big companies here like Walgreens, Caterpillar, Allstate, and AbbVie new people are constantly moving here for work (and then leaving to pursue next rung up the ladder).

There is also quite a bit of diversity here, especially for the midwest, which can make finding exactly what you're looking for attainable for most of us with some time and effort.

If you look at the total number of singles out there right now in Chicagoland it's pretty promising with nearly 500,000 single women and 455,000 single men accounting for nearly 35% of the total population. That's a LOT of singles out there.

Now, sadly having a lot of options doesn't mean that dating in Chicago is easy but it should be encouraging. There are options out there, you just need to be looking in the right places.

New course

Where to meet someone to date in Chicago

I'm going to be honest, it's impossible to make a list of the best places to find someone to date in Chicago that isn't 1,000 items long. The truth is that there are a lot of great options here and it's really going to depend on the type of person you're looking for and in what neighborhood.

Instead, I'm going to share a handful of great places that I've found that are easy to meet Chicago singles that are looking for something more than a single night of fun (we have a separate list of suggestions on where to find Chicago hookups). These are places that tend to have the following characteristics:

  • Lots of singles
  • Fun atmosphere
  • Easy to mix and mingle with new people
  • Quiet enough to actually have a conversation
  • Alcohol is a plus
  • Relatively inexpensive

In my experience, those six characteristics are pretty helpful when meeting other Chicago singles. Now, before we get into some specific recommendations let's talk about apps:

Why you should be using at least one app

If you're not on at least one app right now then you're really at a disadvantage these days. With all the social distancing that's happened over the past few years more and more people are using apps and a lot are ONLY using apps to meet people. Can you still find success without them? Sure, but it can be a real struggle if you have anything else going on in your life.

If you've struggled in the past you can check out our rankings of the best dating apps in Chicago to see what would be right for you. There are a lot of options and it can be really tough to understand which is the best option for you. If you're too lazy to read the full article generally speaking:

  • eHarmony (which you can try free) is the best option for relationships (they have a crazy track record)
  • AFF is best for more casual fun (unless you are crazy good looking)

After trying out over 100 different options we've got a pretty good idea of what's working. Check out our full rankings above for more info. Now, let's talk about some of our favorite spots around town.

Popular singles bar in Chicago

The Best Singles Bars in Chicago

Using the criteria above, we've put together our shortlist of the best bars in Chicago for singles. This is where both men and women can meet some cool people, have a good drink, and enjoy themselves.

This isn't a complete list of all the bars, just the ones worth trying first:

Give these a try. We tried to get different options from different neighborhoods but we've undoubtedly missed a bunch. If you have any suggestions leave them in the comments below.

Singles looking for a date in Chicago at Howl at the Moon

A few other great places to find a date in Chicago

Bars can be a great place to meet other singles but they certainly aren't for everyone. This is a big drinking town but you can still get great results outside of a bar (though that gets tougher in winter).

Here are a few more options that have worked really well and will allow you to bump into a lot of other people looking for dates. Go into it with an open mind and don't take things too seriously. Focus on having fun and spending time in these places as a regular part of your routine:

The Apps Dating Coaches Recommend Most For Dating in Chicago

If your dating life needs a boost, but you can’t seem to meet any more women when you go out, dating apps are the solution. Plenty of women prefer dating apps because it helps them filter out creeps and get to know some really good guys like you. So use at least one of the options below to meet lots of single women!

SiteOur ExperienceOur RatingFree Trial Link
Best For Relationships
Experience Highlights
Experience Highlights
  • Easily the best option for long-term relationships
  • 75% of all online marriages start here
  • 70% of users meet their spouse within a year
  • In-depth signup and matching process
9
Try eHarmony
Best For Casual Fun
Experience Highlights
Experience Highlights
  • The best way to meet women for casual relationships
  • Best results for regular guys
  • Over 60 million active members
  • Not good for long-term relationships
9
Try AFF For Free
Great If You're Handsome
Tinder Highlights
Tinder Highlights
  • Great if you're pretty good looking
  • Very popular, especially if you're 18-22
  • Really focused on photos
  • Becoming more of a dating than hookup app
8
Try Tinder

Couple at a Chicago speed dating event

What about speed dating in Chicago?

Speed dating has become more and more popular, especially during the pandemic when it could be done virtually. If you're busy and have a few extra bucks (it usually runs something like $20-$30 to attend) it can be a very effective way to meet 15-20 other singles in an hour or so.

The way it works is you show up and then a bunch of "mini-dates" where you talk to another single participant for 5-10 minutes. You see if there is any chemistry and then you make a list of the people you want to see again. If you both want to see each other again the organizer gives you the proper contact info.

Pretty easy right? There are a few big Chicago speed dating groups worth checking out if you're interested:

All of the suggestions above should be a great start to find someone interesting to date. Now, let's jump into how to have a great date!

A couple dancing on a first date

Our best date ideas in Chicago and why they work so well

Once you've met someone that you're interested in it's time to plan a date. A lot of people default to dinner or a movie and that's usually a big mistake! A dinner date between two people who don't really know each other often turns into some kind of pseudo interview where you are just blasting questions back and forth and nobody really enjoys it.

Instead, we have a few rules that all of our date ideas follow that you can also use to come up with some new ideas for yourself. A great date idea tends to be one that:

  • Has a fun and upbeat energy
  • Things are going on around you that you can talk about
  • Doesn't involve you sitting face-to-face for long periods of time
  • Has you both moving around a bit
  • Isn't too expensive
  • Doesn't last for hours and hours so you can cut it short if there isn't any chemistry
  • Allows both of you to feel comfortable
  • Has a little friendly competition

Course promo

I'm going to give you a handful of my best date ideas that work well around Chicago and then some very specific suggestions in the next section. These are dates that both people will enjoy as long as they have a good attitude about it going in:

  • Ice skating
  • Take a dance class together
  • Shoot some arrows at an archery range
  • Go to the driving range
  • Check out a street fair (we have tons)
  • Axe throwing
  • Escape room
  • Rollerskating
  • Take a walk with your dog somewhere fun (if you have one)
  • Painting class (preferably with booze)
  • Museum
  • Botanical garden

This is a very short list but you get the idea. All of these are somewhat active and fun and don't involve any great amount of skill. Set the expectations that you're just going to have fun and fool around.

The first date idea that we always recommend

The ideas above can be great first dates but we have a better idea. When people ask our team what the best first date in Chicago is we always tell them the same thing, meet up at a laid-back lounge or coffee shop and get to know each other a bit.

A full-blown date is a lot of pressure and isn't cheap. It takes time to plan and might involve you taking a bus around town to get there. Before you make that kind of investment you want to know that you and your interest have at least some level of compatibility. The last thing you want is to get stuck for hours on a date that you knew 10 minutes in wasn't going anywhere.

Instead, tell them that you're really busy but would love to meet up for a drink to get to know each other a bit. If things go well you can always extend the date into one of the activities above. If it doesn't, you haven't lost much. This also takes a lot of pressure off both of you so you can both relax and be yourselves.

A usual date night at the Drifter

Chicago's best date bars (especially for first dates)

When it comes to great date bars there are a lot of options around Chicago. We're blessed with a lot of options from high-end rooftops to grungy dive bars that are still a lot of fun. I'm going to give you a bit of a mix below but all of these have good drinks, are lively and interesting, and aren't too expensive. You don't want to be spending $20 per drink on a first date when you're not even sure if you like them yet.

Here are a handful of the best date bars around Chicago:

  • The Drifter in River North - 676-8 N Orleans St, Chicago, IL 60654
  • Zebra Lounge in Gold Coast  - 1220 N State Pkwy, Chicago, IL 60610
  • Logan Arcade in Logan Square - 2410 W Fullerton Ave, Chicago, IL 60647
  • Headquarters Beercade in Near North - 213 W Institute Pl, Chicago, IL 60610
  • Recess in West Loop - 838 W Kinzie St, Chicago, IL 60642
  • The Long Room in Lakeview - 1612 W Irving Park Rd, Chicago, IL 60613
  • Woodlawn Tap in Hyde Park - 1172 E 55th St, Chicago, IL 60615
  • M Lounge in South Loop - 1520 S Wabash Ave, Chicago, IL 60605

This is a good list to get you started There are a bunch of other options in different neighborhoods that will work so if you know a bar similar to these don't be afraid to try it.

Single woman

The date spots in Chicago that we love

Taking inspiration from our ideas above I'm going to share some of Chicago's best date spots. They are spots that we've seen a ton of people have great dates at and we're confident you can do the same.

Keep in mind that the time of year will make a difference with some of these (being outside for hours in January doesn't make for a great date) so you've been warned.

Tango Sur on a busy date night

The date night restaurants in Chicago that really stand out

When it comes to a date we tend to recommend avoiding a traditional dinner date for at least the first few dates. Dinner dates tend to be pretty boring and you're locked into a face-to-face conversation/interview for two hours. Even if you're a great conversationalist it can get a bit stale.

However, if you're in a long-term relationship or just want a date night restaurant to eat at before doing something more fun we've got some solid choices for you that won't break the bank. If you want more expensive places those are easy to find on your own!

These are restaurants that have both great food and an atmosphere with plenty going on for you two to talk about:

Map of Chicago's best dating ideas and spots

To make things even easier for you we've put all of our recommendations together into a simple map. You can use this to plan out your night and find the recommendations that are closest to you:

Join Our Newsletter

No Spam. Just Higher Dating Success.

Leave a Comment