There are first dates. And second dates. And third dates. And then you reach a point when you stop keeping track because all you do is eat together. Congrats if you've made it that far. "Date night" can mean a lot of different things depending on whether you're just getting to know someone or know their every move. Either way, a good meal is always important. Here are our favorite spots for date night excellence.
We love a classic French brasserie, and they don't make 'em like Le Bouchon anymore. Nothing about Le Bouchon is overly sexy, eye-catching, or exciting, but that's why we love it. It's a typical Brasserie, which makes it the total package. Stick to the classics like french onion soup, steamed mussels, or steak frites, and it won't disappoint.
Parachute never ceases to impress us. The food is a mix of Korean and American creations that aren't exactly Korean, nor are they American. Just don't call it fusion, because that's a bad explanation too. The important thing is Parachute is always delicious, which will make for an exciting night out whether it's an early date or your usual date involves watching reruns on the couch.
Ruxbin is not for an early date - it's too risky. If the date's going poorly, you'll be stuck in a quiet space with a $65+ tasting menu. But those elements make it ideal for someone you already know well. Ruxbin is also BYOB, so bring that nice bottle of wine you've been saving for a relaxing and enjoyable dinner together.
You can count on Monteverde for excellent Italian food in an atmosphere that's always crowded. The pastas are some of the best we've ever had, so make sure your meal revolves around them. If you're looking to get some protein in the mix, get the ragu alla napoletana, which can only be described as nothing less than ridiculous (involving pasta, sausage, soppressata meatballs, and a large braised pork shank). You and your date are like two meatballs in a pod.
Whether you want to prove to someone you're interesting or are trying to keep things alive in your relationship, get a little exotic at La Sirena Clandestina. It's not a total stray into the weird, but the Brazilian and South American food here will at least keep things interesting. Pretend you're on vacation and try their classic caipirinha or pisco sour cocktails.
Stuffy French restaurant Maude is not. This is where you come to eat all of your French food favorites in a cool, modern space. If that's not enough, we once saw Patrick Kane on a date here, so if it's good enough for him, it's good enough for you.
Vincent is the perfect mix of action and romance in Andersonville. It's an American bistro with plenty of things on the menu for everyone to eat, but don't miss out on the various styles of mussels. Put it this way - Vincent is good for your love life.
No matter what kind of relationship, spontaneity is always a good thing. And since Avec doesn't take dinner reservations, it makes having no plans the best kind of plans. The minimal, sleek wood design makes Avec a cool place to hang, and the food is always excellent. Never pass an opportunity to order their focaccia or chorizo-stuffed bacon-wrapped dates.
Date night doesn't always have to revolve around a big formal dinner. Sometimes the focus of the night can be excellent cocktails with quality food in the supporting role. And that's exactly what you can expect at Scofflaw. They also serve warm chocolate chip cookies at midnight, and those can turn around any terrible date.
A traditional steakhouse is always a good time, but it can also be too forced for a date night. That's why you should check out Boeufhaus instead. It's the perfect ambience for date night: small but not cramped, dimly lit with low hanging lights, and music that's anything but boring.
Twinkly nights and a pretty patio are pretty much a slam dunk for any successful date night, and Ada Street delivers on it all. Sit outside and share small plates in a cute little courtyard if you can, but know that the inside offers a similarly pleasant experience.
La Scarola721 W. Grand Ave.
Dates don't have to be flashy and impressive. Sometimes it's best to put yourself and your date in a relaxing situation where you can loosen up, and La Scarola will put you in the mood to do just that. It's our favorite old-school Italian spot where you can settle in over a bunch of pasta and wine. And the key to any successful relationship is more wine.
Bavette's great for a decadent date night out as long as you don't have any plans for afterwards. The food here is traditional steakhouse, with an excellent "Le Boeuf" section plus a solid list of classic sides. But the ambiance is decidedly not traditional: a cool, dark space with big red booths and a retro feel. Prepare for all of the meat and butter to put you to sleep when dinner is done.
Whether you’re just starting to really get to know someone or you’ve known them for a while, it can never hurt to remind them that you know where the cool sh*t is. Head towards the borders of Ukrainian Village and Humboldt Park to find Marta hiding at the corner of Chicago and Western. There's a sense of coolness here, even if you're not very cool yourself.
Looking for a more traditional night out with appetizers, entrees, and a nice bottle of wine? Boka has been and continues to be a strong move. The place has been going strong for about a decade, and a recent revamp has kept it as great as ever. The food is very modern-American and creative, and you really can't go wrong ordering-wise.
A long-standing Infatuation favorite for a delicious and enjoyable Italian meal. Riccardo Trattoria has all the feels of a typical trattoria, meaning it's nice, but not too nice. It's all classic Italian food, and you should feel free to order anything on the menu. Altogether, it makes Riccardo a great date spot that doesn't feel like it's trying too hard. And we're all about not trying too hard at anything in life.
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