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.
All restaurants featured on The Infatuation are selected by our editorial team. The Best Bars For A First Date In Chicago is presented by Monkey Shoulder. As a whisky that’s made for mixing, Monkey Shoulder believes that adult life - and dating - doesn’t have to be so uptight. Check out our full collection of laid-back dating guides here.
It would be easy to drive right by Osito’s Tap - this small bar is hidden on a side street along the busiest stretch of Little Village. But that also means this quiet little bar never gets too busy. It has shareable bar bites like tlayudas or wings tossed in a tasty mole, a great side patio, and is a perfect spot for drinking and laughing with someone you might (possibly) consider going on vacation with.
The Victor Bar
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. Instead of canceling your date, plan on going to The Victor Bar. Why? 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.
Recess in the West Loop is a theme bar, and the theme is basically “City Hall,” which means menus are made to look like municipal forms and cocktails have names like the “Alderman’s Choice.” And while government buildings and red tape aren’t what we’d normally consider romantic, we promise this place is fun. The outdoor space is huge (14,500 square feet), and includes tables situated inside repurposed shipping containers, giant games of things like Connect Four, and it even has an outpost of Bob’s Pizza. In conclusion, come here, play games, get drinks, order pizza, and get to know each other.
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 an enjoyable vibe, 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 wealthy people 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. 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, and Pizza Fried Chicken Ice Cream next door. 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.
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.
Grapes & Grains
As the name implies, the focus at this West Loop lounge is on wine and whiskey. Alongside a big list of those two things, Grapes & Grains has a lot of space and live music Thursday, Friday, and Saturday nights.
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 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.
While Hubbard Street in River North can be very busy, there are a couple of sleepers that are good for casual drinks. Like Celeste, the kind of cocktail bar where you can 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 upscale 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.) Its high ceilings, brick walls, and colorful murals make it a comfortable place to sit, and the long 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.
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 while drinking beer and playing 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.