You're finally ready to settle down and find that special someone. And thanks to mom and grandma not-so-subtly signing you up for a bunch of dating subscriptions, you've been planning a lot of first dates as of late. First dates are important, though, 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 or third if you make it that far.
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 Shenanigans, 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 Hanggee-Uppe, but the two places have nothing in coming. This is more of a low-key neighborhood bar where you can grab classic cocktails and bond over the fact you both loved Tamagotchis as kids.
Kimski is the perfect combination of casual neighborhood tavern and slightly trendy hang. It’s attached to and owned by Maria’s Packaged Goods and Community Bar - which will show your date you know the good local spots - but the newer Kimski part has a more lively warehouse feel and serves fun Polish-Korean bar food, proof you also know the cool new spots.
You’re a busy person with a demanding job and your date is too. It’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. You’re going to Pearl Tavern, an oyster bar with a classic feel that’s nice enough for this situation but is also not too over-the-top.
On a first date, you never want to act like you take yourself too seriously. (Even if you’ve changed your outfit nine times already.) Suggest the casual but consistently enjoyable Bangers & Lace. There’s an extensive beer menu, great cocktails, and it feels like a casual Midwestern lodge where you can sit and hang. There are a few locations these days, but the Wicker Park location is our go-to spot. You’ll be golden thanks to a dark yet lively space where you can sit and talk, and your hair looks great - we promise.
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.
Take a chance and commit to the night being a good one by taking a date to Lost Lake, the Logan Square tiki bar. You might feel a little weird ordering a “Bunny’s Banana Daiquiri” or “A Lonely Island Lost In The Middle Of A Foggy Sea,” but rest assured that’s the move here. The full-blown tiki theme with bamboo chairs and floral wallpaper makes the whole atmosphere playful and kind of fun. And the sooner you accept the fact you’re drinking a cocktail out of a totem pole shaped glass with colorful crazy straws, the sooner you can relax and be yourself before awkwardness comes into play.
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 a bunch 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 an old-school tavern feel, but in a grown-up way, which makes it a great place to post up at the bar over interesting drinks like the “By The Fire” or “Fool’s Gold” that each contain at least six ingredients (half of which we’ve never heard of). But we do know the end result is great, and we also know this is an excellent place to get to know someone on any given night. A few basic food options like an antipasto or charcuterie board ensure you can hang for a while and order an extra drink.
Most of the bars in Lincoln Park involve copious amounts of Fireball shots and sticky floors thanks to spilling of said Fireball shots. But not Barrelhouse Flat. It’s a more grown-up place, with a lively vibe, good drinks, good food, and a more quiet lounge-like space upstairs. Both floors are good settings for a first date, so feel free to scope out the scene and decide which is best for you.
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, we have 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 shtick. 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.