You’re finally ready to settle down and find that special someone. And from the number of dating apps you’ve downloaded recently, it’s clear that you mean business. First dates are important, so consider going somewhere other than your local corner bar where the bartender knows your name. Maybe you want a wine bar, maybe you want funky cocktails, or maybe you want the option to order food in case things are going well.
So rather than ask your friends who have been in relationships for years, check out our list of bars that are great for a first date. Or second date, or third, if you make it that far.
Complaining about modern dating is 96% of modern dating. It makes us all feel better to pretend that our awkward meetups are the fault of The Algorithm, and that dating hasn’t always been terrible. But whether you and your date met on an app or in the basement of your synagogue, you can pretend you’re back in the ’50s at The Pink Squirrel. The booths are small and romantic, the drinks are time-tested, and there are two lanes of duckpin bowling - a flirty, low-stakes version of bowling where you don’t have to put on someone else’s shoes.
Best Intentions is a great first date bar because it’s more versatile than tearaway pants. Take your pick: do you want the date to have a sort-of divey feel, or are you looking for an outdoor tiki-style hang? Foodwise, are you thinking a $5 cheeseburger or some calf liver pate? Because they’ve got all of these, along with a long list of booze that’ll satisfy your date even if they only drink fancy mezcals. And in case you’re looking to show off your hand-eye coordination, they have Big Buck Hunter too.
Because you have the hubris of Jeremy Renner releasing a lifestyle app and a rock album in the same year, you scheduled a haircut and first date within hours of each other. It was a bad haircut (all the styling products in the world can’t help), and now you’re freaking out about your weird face shape. Instead of canceling on your date, plan on going to The Victor Bar. Not because it’s filled with asymmetrical people who’ll make you look good by comparison, but because it’s just really dark. More importantly, the space is intimate and the cocktails are great. Next time, though, give yourself a few buffer days after your appointment.
We’re big proponents of Pub Royale in general because it’s great for so many occasions, and that includes a first date. The funky Indian-English pub has quirky decorations, quality drinks, and great food. That means you can chat it up over beers or one of their many variations of Pimm’s Cup drinks, and transition into food if it seems like a good idea. Pub Royale is still a bar, though, not a restaurant, which helps keep things casual while you feel each other out.
Gold Coast bars usually mean old rich guys in The Viagra Triangle or a bunch of drunk twenty-somethings staggering around Division Street. And while there are nights when it’s appropriate to spin the wheel at She-nannigans, a first date is not one of them. Turn your attention instead to Sparrow, where there’s no food but it’s a great spot for a first meeting over drinks. It’s next to The Hangge-Uppe, but the two places have nothing in common. This is more of a low-key neighborhood bar where you can grab classic cocktails and bond over the fact that you both loved Tamagotchis as kids.
Rose’s is a little dingey, cash only, and there’s a pool table that’s mostly in the way. Despite all that, it’s one of our favorite spots to meet someone for a first date. It’s centrally located for people living on the north side, and drinks are cheap enough that you can stick around for hours without making a hundred trips to the ATM. There are a few couches that make it feel like a basement, but your date will almost certainly go much better than your junior prom afterparty did. Plus, there are free pretzels and the jukebox is loaded with hits - if you can’t manufacture some romance out of all of that, good luck.
Maria’s is the perfect combination of casual neighborhood tavern and trendy hangout. There’s a homey wood-paneled bar on one side, a bigger, industrial-looking bar on the other, Kimski attached to the back serving delicious Korean-Polish bar snacks, and a great soundtrack every night of the week. Plus, since it’s also a store, you can easily grab a six-pack to go, if you decide to continue the date at your place or theirs.
The Long Room is an excellent place for a first date because it’s an excellent place to have a conversation in general. True to its name, there’s a super-long bar here, but also comfy booths and a secluded patio out back. They have a solid list of craft beers and the kitchen is open until 1am on the weekend - but if the conversation’s really flowing and you’re here until close, head across the street to Diner Grill, which is open 24/7.
Going on a first date can be hard on the nerves, but know that you’re in good company at Guthrie’s, because most of the people here on any given night are also on first dates. There are plenty of safety nets if the conversation starts to drag, like a wall of board games and a stack of delivery menus you can use to come together and strategize the BYOF situation. Break out Parcheesi, order some pad thai, and remember to be a good, active listener.
Ipsento 606 lives a double life, like Batman or your friend’s dad who had a secret family. By day, it’s a coffee shop filled with laptops and pour-overs, but at night it’s a dimly lit cocktail bar with an eclectic draft list, wine, and cocktails. Since it’s somewhere in between the two, it’s a great spot to go if you or your date don’t drink. They’re only open until 9pm most nights, so grab a seat by the window overlooking the park, sip on a coffee cocktail, and end the night with a romantic walk along the 606.
Woodlawn Tap (or “Jimmy’s,” depending on how often you go) has been around since the ’50s, and it’s the type of place you should head to if the shared experience of taking down a pitcher of light beer sounds more romantic to you and your date than a couple of $15 craft cocktails. There aren’t any frills - so be prepared to bring your A-game, along with cash - but we’d be willing to bet that more first dates here end up in marriage than any other place on our list.
You’re a busy person with a demanding job and your date is, too. That’s probably why you’re both single, which means you owe it to yourself to make this meetup happen. But the fact that you live on opposite sides of the city is making things difficult, so you want to grab drinks close to both of your offices in the Loop. Go to Game Room, on the second floor of the Chicago Athletic Association. There are lots of things to do while you get to know each other, like bocce, shuffleboard, foosball, and pool, and they also have a not-too-pricey-for-the-neighborhood food menu.
You’re feeling optimistic because a close mutual friend set you up with someone and swears you’ll be soulmates like a real life Allie and Noah from The Notebook. You’re excited and consider a full-blown romantic meal: maybe fondue? Please, no fondue. Instead, go to Scofflaw, where you can sit and talk over quality cocktails, particularly the gin-focused ones, and maybe even good food. And if you make it to midnight, the free, freshly baked chocolate chip cookies will make you both fall in love - at least with the cookies, maybe not each other quite yet.
Taking a date to a tiki bar might feel like a big swing at first, especially if you’ve only ever seen the massive line snaking out of Lost Lake on the weekends. But it’s much more manageable during the week, and the playful atmosphere can be a great choice for a date with someone you’re meeting for the first time. The drinks are delicious, with names like “Salty in all the Right Places (Theme for a Nude Beach),” and once you realize that you’re drinking a cocktail out of a shell with colorful crazy straws and banana dolphins, you can relax and be yourself without the typical awkwardness of a first date.
Your date said River North would be an ideal neighborhood for drinks and you haven’t been out there since that time you blacked out at Social 25. Fear not. While Hubbard Street is full of places where you definitely don’t want to be, there are a couple sleepers that are good for casual drinks. Hit up Celeste, the kind of sleek, dark, and sexy cocktail bar where everyone is well dressed but you can still sit and have a real conversation instead of standing around pounding Bud Lights. Leave that for another time, even if that time is as soon as this date ends.
Billy Sunday has a grown-up tavern feel, which makes it a great place to post up at the bar and order drinks made by bartenders who know what they’re doing. No matter what you order you can be sure the end result will be great, which means you can direct your focus on getting to know your date. A small menu of bar snacks like artichoke dip and brandade ensure you can hang for a while and order an extra drink or two.
Arbella is a cocktail spot next to Tanta (and owned by the same people) that has a similar type of worldly appeal. Its high ceilings, brick walls, and colorful murals make it a comfortable place to sit, and the cocktail list reads like a map of the world in alcohol form. Maybe try something you’ve never had before, like a PB&J cocktail - just like the bar itself, it’s the ideal level of interesting and fun that will trick someone you’ve never met before into thinking you’re actually cool.
Activities are fun for a first date. But rather than half-assing it with a trip to the Lincoln Park Zoo or going all-out with indoor skydiving, there’s another option: alcohol and video games. Bond over childhood memories while you drink beer and play Donkey Kong at Emporium.
You matched on Tinder after similar interests including baseball, romantic comedies, and wine. Take advantage of your (highly coincidental) shared interest at Webster’s Wine Bar, where there’s an extensive selection of wines by the glass. If things are trending in the right direction, order a bottle and enjoy it with small snacks like bacon-wrapped dates or venison tartare.
Feeling comfortable is the key to any successful first date. And if that’s your priority, head to Lone Wolf in the West Loop. It’s simply a quality bar without any schtick. There are always people there, so it’s not too quiet, but rarely is it a full-on party where you’ll need to fight for space. Stay calm. You got this.