First dates can either lead to a lifetime of sharing a Netflix account, or be a 30-minute time-suck where you just talk about the last two movies you’ve seen. You never know how things will go - but if you want to give yourself the best chance of having a good time, it’s important to pick the right place.
Here are 18 of your best options. All of these spots are relatively casual (so it won’t look like you’re trying too hard), but they’re also impressive enough to make it seem like you put some actual thought into the night. You can get a full meal at all of them, but they’re all perfect for either a 20-minute meet-and-greet or a three-hour date before you decide you’ve found someone to split rent with.
When you hear “soda fountain,” you might think of someplace your parents would take you after a seventh-grade orchestra concert. And while Spinning J in Humboldt Park is technically a soda fountain, it’s also a fun BYOB spot that makes great sandwiches with housemade bread, desserts like key lime hibiscus pie, and pizza on Friday nights. If your date isn’t charmed by sitting in a little booth and pouring rum into their milkshake, they’re clearly not the one.
Good Measure is permanently closed
You want to show that you put some effort into planning the night, but don’t want your date to know it’s the only thing you’ve been thinking about all week. Good Measure in River North is great for this - it feels like a dive bar, but is actually a restaurant with excellent food. There are dishes like Nashville hot duck livers and burrata with plum jam, and the loud punk music will keep your date from your hearing your shrill, nervous laughter.
The Delta is a laid-back place in Wicker Park with consistently delicious Southern small plates (like tamales and hush puppies), plus a secluded back patio. They don’t take reservations, so it’s a good idea to be prepared with a back-up plan. If it’s busy, just put your name in and grab a drink at Dorian’s down the street.
Cellar Door Provisions
You probably want the other person to think you’re cooler than you are, which is why your profile picture is of you wakeboarding, even though you were only upright for 0.6 seconds. Cellar Door Provisions in Logan Square is essentially the restaurant equivalent of the ideal dating profile - the small space is attractive, the seasonal food is delicious, and it has great taste in music. So unlike people who are “looking for the Jim to their Pam,” coming here never feels boring.
This is a dark and busy pub in Andersonville - so it might not scream romance at first, but all the activity is a good distraction to act as a buffer for any nerves-related awkwardness you might feel. Hopleaf has a long beer list and great sandwiches, like the duck reuben or the fantastic CB&J (cashew butter with fig jam). Grab a seat in the dining room, or order at the bar and hang out there all night.
If you want to show that you’re very low maintenance and really appreciate good food, go this Belizean spot in Marquette Park. Garifuna Flava has excellent chicken and oxtail stew, and an affordable drink list full of tropical cocktails. Plus, you can walk in anytime, so when you come back here every year for your anniversary, you won’t need to remember to book a reservation months ahead.
All Together Now
All Together Now is a cafe and market in West Town that’s great for talking over cheese, charcuterie, and a glass of some natural wine you’ve never heard of before. There’s not a ton of space here, but on weeknights you won’t have a hard time getting a seat at the bar or at one of the small tables. If after the meal you don’t want the conversation about each other’s childhood pets to end, you can always get a bottle of wine to go and introduce them to your dog.
90 Miles Cuban Cafe
First dates feel easier in the summertime. You don’t need to put six layers on, or take an Uber someplace that’s normally a five-minute walk from your house. You can just bring a bottle of wine to the beach, or relax on a charming patio. But if you went into winter single, you should take your date to 90 Miles in Logan Square. This BYOB restaurant has great Cuban food like empanadas and ropa vieja, and a heated patio that can help you both forget you each just spent an hour sitting in front of your SAD lamp before dinner.
Lula Cafe is a farm-to-table Logan Square staple with plenty of vegetarian-friendly entrees (like sweet potato gnudi or peanut satay noodles with tofu). And they serve an always-changing $45 tasting menu on Monday nights, which is great because 1) a lot of places are closed on Mondays and 2) Alinea isn’t a great place to ask somebody how they got into consulting.
You might want this date to be over after a round of drinks, but if your date passes the normal-person Turing test, you can eat a great meal at Pub Royale in Wicker Park. The British and Indian menu means you can drink a specialty Pimm’s Cup, and get dishes like butter chicken and gobi manchurian. Or, you can have exactly one turmeric daiquiri, and “remember” you have a really early morning tomorrow.
If you’re doing a tried-and-true “Chicago date at the Lincoln Park Zoo,” Riccardo Trattoria is where you can grab dinner afterward. It’s a busy, old-school Italian restaurant that’s right near the zoo, and has a long menu of great pasta. Drink a bottle of wine, and laugh about what you saw that koala do in front of those (now traumatized) kids on their school field trip.
Impress them with excellent food and go to Parachute in Avondale. This place is across-the-board fantastic, with delicious Korean dishes like smoked yuba ssam and spicy stir-fried rice cakes with pork. It’s also small and very popular, so don’t plan on walking in and getting a table. Make a reservation, and see how impressed they are when you confidently ask for extra sour cream butter to go with the baked potato bing bread.
Vincent in Andersonville is good for a first date that you want to feel a little fancy (without being stuffy), and kind-of intimate without being weird and quiet. Order burrata and the skate wing, and since Andersonville is one of those cute tree-lined neighborhoods, plan on an after-dinner walk. Grab a piece of pie from First Slice, or go to Simon’s and listen to live music.
If you want to go somewhere loud and sceney, hang out in the downstairs bar area of Bar Siena. It’s a fun spot with solid pizzas and pasta, and since the West Loop is like Disneyworld, it’s easy to keep the night going after dinner. You can go to a dark izakaya with great cocktails, or a loud patio where you can drink tequila out of frozen shot glasses. It’s like It’s A Small World, but with booze.
Dusek’s, the restaurant attached to Thalia Hall in Pilsen, is basically a full-service date night spot. For starters, this upscale tavern has great food, with small plates like shishito hush puppies, and a sourdough pretzel covered in shredded cheese. And after dinner, you have the rest of your night planned: head downstairs to Punch House for some excellent punch drinks, or go next door to Tack Room for cocktails and live piano music.