Great Chicago Dating Tips to Make a Powerful Impression | Part 1

Updated: May 27

If you can navigate the tough commutes and the cold winter, the dating scene in Chicago can be a great time. Here's a handy guide to find just some of the awesome spots that Chicago has to offer.


Finding the Right Neighborhood for Dating in Chicago

Chicago is not necessarily a city you’d associate with romance. But Chicago has plenty to offer for fun and exciting date nights. And in this post, we’ll cover what you need to know, from finding the right neighborhood to braving the cold winter temperatures to best places to try.

Let’s start off with neighborhoods. Check out a text exchange that WBEZ listener Liz Meenan shared between her and a potential date, it may give you a laugh:

Potential date: Where do you live?

Liz: I'm over in Logan.

Potential Date: I'm in Uptown. This is never going to work.

And alas, this prophecy came true; Meenan and this person never met up. Chicago daters prefer not to stray far from their neighborhoods for romance, or to date someone who lives along a different CTA line. And as a matter of fact, this is backed up by data! According to OkCupid, Chicago daters send more messages to people who live closer to them, as well as along the nearest CTA ‘L’ line.

a mirrored art installation in a cosy central plaza

Although it’s easier to date with others who live near you in Chicago, one Chicago couple told WBEZ a story of overcoming the inter-neighborhood odds - Chris and Elizabeth Biddle. When the two first met, at a burlesque show, Chris was living near the lake in Edgewater and Elizabeth was living on the border of Norridge, on the far Northwest side. To visit Elizabeth, Chris would make the two-hour trip from the Red Line to the Blue Line to the Harlem Stop to the bus. And while they laugh about it now, it certainly was no picnic. Chris and Elizabeth say that the distance introduced difficulty and caused arguments early in their relationship, which ultimately stopped after Elizabeth moved further into the city. Chris and Elizabeth are now married and live together in Edgewater. "It takes 30 second to go from one room to another," Elizabeth says.

The TL;DR? If you are looking to date in Chicago, it’s easiest to stay local. And if you are willing to travel further, more power to you! But just know that it could be an obstacle you’ll have to overcome early on.

Mastering the Dating Scene During Chicago Winters

Indeed, it seems like winter is always coming in Chicago. While summer months of Chicago feature absolutely glorious weather, they are often short lived, forcing residents to find ways to deal with dating in the cold. Comically, when WBEZ asked people about their Chicago dating experiences, the phrase "cuffing season" was used multiple times. Tecarra Carmack, 29, is originally from North Carolina and learned the phrase when she arrived in Chicago. Cuffing, she explains, is when, "in the winter months you have your main boo, but in the summer months you have multiple boos."

While the phrase "cuffing season" is only a few years old, the concept is certainly not. Daters in their 30s and 40s had other names for it, among them: "nesting," "harvest season," "catching a boyfriend or girlfriend" or, "a warm stone in the bed." But all of these phrases get at the same idea: a tendency to find a partner to keep you warm in the winter and then have some fun when spring arrives and you’re looking for a fling.

And sure enough, there’s some data to show that this is actually a real trend. An analysis of Facebook relationship statuses showed that yearly peaks for break-ups occur in May-June, when “cuffing season” has already come to an end.

a cityscape with a semi frozen river

Chicago's wintry weather also tends to expedite how quickly people stay over at each other's houses. For example, Leyla Royale and her now-boyfriend Nicholas Spence went on their first official date on Valentine's Day, 2014 - a bold move! That date turned into a surprise overnight stay when his car got stuck in the snow outside of her Logan Square apartment. This phenomenon of "snowpocalypse sleepovers," was mentioned by other daters WBEZ spoke with as well.

Unsurprisingly, people are far more reluctant to go on dates in the winter. And when you’re dealing with sub-zero temperatures, who could blame them? So just bear this in mind if you’re planning on dating in Chicago - make the most of those warm, summer months!

Best Spots to Visit on Dates

Now that you’ve mastered the basics, you’re ready to explore some of the best spots to actually go on your dates! Let’s start off with some creative ideas:

  • Sneak into Chicago’s most secret bars: Impress your date from the start by going to one of Chicago's hidden speakeasies. From secret cocktail lounges to a subterranean Japanese izakaya, check out all the best places Chicago has to offer. Even if you don't hit it off, at least you'll have an adventure getting into these swanky spots.

  • Hit up a free museum day at the best Chicago museums: A free museum visit is the perfect, low-stakes activity: if your date isn't into it (or they're way too into you), you have an easy way to head out. But honestly, you won't even want to leave the best Chicago institutions. If you're willing to plan out in advance, you can take in masterpieces at the Art Institute or gaze at tropical fish while strolling through Shedd Aquarium—all without spending a dime.

  • See a free movie screening in the park: Seeing a movie on a first date sounds like a good idea, until you realize you're just sitting silently next to a stranger (at least for the time being) for the next two hours. Instead of crazy high prices and awkward movie theater silence, why not check out Chicago Park District's annual “Movies in the Parks” series, which offers free entertainment from Rogers Park to Hegewisch.

  • Get your minigolf on: Minigolf is ripe with light competition and ample opportunity for flirty banter. The mini golf course at the Diversey Driving Range, situated right in Lincoln Park near Belmont Harbor, is an awesome first date spot. The course is suited for golfers of all ages and skill levels, with plenty of bridges and waterfalls for a fun date.

  • Take a stroll through the Lincoln Park Zoo: A classic date activity in Chicago, taking a walk through the Lincoln Park Zoo is a great way to get to know someone. Visit the 1,200 animals, from apes to zebras, at one of the few free zoos left in the entire country. And if you’re feeling good, cap off your trip to the Lion House with a coffee at Café Brauer or drinks at the J. Parker.

  • The Delta: You can’t go wrong with The Delta in Wicker Park, especially when you get a seat on their awesome back patio. It’s a casual, laid-back place with good cocktails, some of which even come in larger “vases,” in case you find out you have a mutual love of drinks made with mezcal and watermelon juice. And the short menu of Southern small plates won’t trap you into a long dinner if you discover that your taste in drinks is the only thing you have in common.

  • Forbidden Root Restaurant and Brewery: This West Town brewpub is in a remodeled old theater, which will give you something to make small talk about. It doesn’t have a very bar-y atmosphere - there are steampunk light fixtures and hidden TVs that only come out when a Chicago sports team is in the playoffs. The food and beer are both solid - there are bar snacks like fried giardiniera and chili popcorn, and the burger is fantastic - and you can even ask for a quick tour of the brewery in the back.

  • Little Bad Wolf: This Andersonville bar’s expansion has made it a great, comfortable date spot. There’s indie music playing at just the right volume, it’s busy (but not unpleasantly so), and you can eat one of the best cheeseburgers in Chicago, along with other things like tacos and bao.

  • Centennial Crafted Beer & Eatery: This is the perfect place to meet up if you’re both in River North. Centennial is a low-key spot with a great craft beer selection and interesting bar food. Many of the dishes have an Indian twist, and the space looks like the hull of an old ship - pretty neat!

  • The Press Room: The West Loop is a busy neighborhood, but you wouldn’t know it if you went to visit The Press Room. It’s a wine bar in the basement of a building on a secluded side street, and it’s rarely crowded. They have a great selection of wines, really good cocktails, and a short small plates menu (with things like chicken liver mousse) that goes well with both. So it’s an easy place to hang all night.

The Bottom Line

As you can see, if you know how to navigate the dating scene in Chicago, it can be a great time. Be wary of tough commutes, plan ahead for a cold winter, and check out some of the awesome spots that Chicago has to offer. And in the next post, we’ll cover what you need to know for a fun night out on the town.

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