You just got a fantastic haircut (if you do say so yourself) and you know that no matter how many instructions and products you’re given to help “recreate it at home,” tomorrow it will probably look like you did it in the dark wearing giant Mickey Mouse gloves. So, you want to go someplace where people other than you, your phone’s camera, and your spider plant will be able to appreciate it. You need a spot that’s fun(maybe kind of a scene) and you want to eat something good, too. These 17 places should do the trick.
The Listening Room is a new bar and listening cafe in the Loop. What’s a listening cafe, you ask? According to their website, it’s “a clubby dining experience with a state-of-the-art audio experience.” It turns out the “listening” part really just means that the sound quality is really good, and it feels more like a lively cafe than a club. The menu has dishes like tender chicken thighs with crispy skin, mac and cheese that gets melted raclette poured over it tableside, and roasted carrots served with a fluffy coconut mousse and topped with peanuts. So come here when you want to eat good food, and pretend you’re in a music video.
If your hideous split ends are what have been holding you back from eating someplace with white tablecloths and servers in tuxedo jackets, you’re in luck. You will find all of these things at Adalina, a new upscale Italian restaurant in the Gold Coast. This spot walks the line between fancy and overly formal - both because of the friendly service, and because it’s busy and loud enough that you won’t feel like you’re eating in a library. Plus, the food is really good. The menu has dishes like gnocco fritto with prosciutto, whipped ricotta, and honey (a fantastic starter) - along with housemade pastas, and entrees like a tender bone-in veal parmigiana. Basically, it’s the kind of fancy place where you can show off your lack of split ends and crack a joke with the person making your tableside salad.
Mama Delia is from the same team as Beatnik in West Town, which, by the way, is also on this guide. And this Spanish spot in Wicker Park has a similar atmosphere - meaning loud music and ornate furniture, all of which make you feel like you might be an extra in a Wes Anderson movie. Come here to catch up with friends over cocktails and share dishes like conservas, tartare, or a cheese plate (in addition to styling tips).
Nothing says “I finally got a haircut from a licensed professional” more than going out for a martini and perfect bone-in ribeye from Bavette’s. For one thing, it’s the best steakhouse in the city. And you can eat inside in a dimly lit space that feels like a speakeasy, or get a table on their sidewalk patio. Either way, don’t leave without ordering the chocolate cream pie.
If you finally got that shag but are feeling a little uncertain, Osito’s Tap is an excellent option. This small bar is hidden on a side street along the busiest stretch of Little Village. The small bar never gets too busy, so probably won’t be filled with all your exes who aren’t ready for the bold new you - but that doesn’t mean it isn’t fun. 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 giving your stylist’s business card.
La Luna is a fun Mexican restaurant in Pilsen. Thanks to the colorful murals, fantastic hip-hop soundtrack, and occasional live music, this place feels like a party. It also doesn’t hurt that they have fantastic food (with dishes like enchiladas, flautas, and quesabirria), and Happy Hour from Tuesday-Thursday with $10 margaritas and $3 tacos. Those deals will be much appreciated after how much you just spent on color-safe shampoo and conditioner.
Rose Mary is a West Loop Croatian spot, and reservations are (very) hard to get. But because you’re an ENTJ who pre-books their appointment before leaving the salon, you can probably schedule dinner here after your next cut. And the fact that Rose Mary is very popular means you’ll be surrounded by lots of people who have the opportunity to admire your hair. Plus, the food is really good - with dishes like cevapi, delicious crni rizot topped with grilled squid, and some incredible pastas.
This brightly lit Spanish restaurant in Lincoln Park feels like a coffee shop, which makes sense, because they’re open all day for pastries and sandwiches. And while your hair looks great in natural light, it will be absolutely luminescent under the string lights in their back patio. It’s a lovely space to hang out - small (only about six tables), with Spanish music playing in the background. And it’s also the perfect place to eat pretty (and tasty) dishes like tiny pieces of french toast topped with foie gras and jam, a wonderful vegetable pisto with manchego and a duck egg, and tender Iberico pork with pickled snap peas. It’s BYOB, so grab a bottle of wine from The Big Apple grocery store across the street.
For delicious pasta in a space that’s busy - but not as crowded as Rose Mary - go to Testaccio in Humboldt Park. The menu is short: some hot and cold small plates, two Roman-style pizzas, a few entrees, and fantastic pastas like cacio e pepe and mezze maniche. It’s all great, the space is lovely, and it’s the perfect low-key place to flex your fresh fade.
Do you love Avec in the West Loop but don’t think that tiny restaurant fits enough people to see your bob? Check out Avec’s River North location. It’s about 56 times larger than the original Avec, has a longer menu full of Avec classics (like the chorizo-stuffed bacon-wrapped dates and taleggio flatbread), and also a lot more small and large plates, pastas, and pizza. Plus, you can almost always walk in and grab a seat at the giant oval bar in the middle of the restaurant - giving your haircut the 360 degree view it deserves.
You don’t go to Bandit for the food, which is hit-or-miss. You end up at this smallish spot in the West Loop because it feels like a house party - the kind you used to go to that used Apple Pucker as a mixer, and had a keg in the basement. Come here for drinks and bar snacks (like fried halloumi or pretzels with Merkts cheese) before giving your new look a Big Night Out in the neighborhood.
Much like your printed-out Pinterest board of celebrity haircuts, Bar Siena is on the bubble of being obnoxious, but the great food makes up for it. The space is always loud and crowded, with a huge bar dominating the first floor and a larger dining area upstairs that’s generally full of groups. You should get a pasta or pizza, like the pillowy gnocchi or the delicious prosciutto and fig pie - and if, after dinner, you want to give your great hair a second outing, head to Bar Siena’s enclosed takeout window (Bombobar) for dessert. It has great Italian donuts and gelato, and is always full of people, too.
From the guy wearing an earpiece at the elevator, to the twinkly-light-and-plant-filled space, to the dressed-up people, there’s no mistaking that Aba is a scene. There are also two busy, large bars, and a huge rooftop patio (complete with seasonal glass domes that will make sure to protect your hair from the elements). Most things on the Mediterranean menu are meant to be shared, so you can come here with friends and split six types of hummus, plus five varieties of kebabs.
You’re feeling it tonight, but not to the point that you want to have dinner in a borderline club. So check out Eleven Eleven, a West Loop bar that’s cool but relatively relaxed. They have a long wine list, and if you want, the bartenders will talk to you extensively about the selection. But there’s also a very good food menu, with options like cacio e pepe, and a burger with crispy kale that’s delicious, but will make you need to check your teeth before smiling at anyone.
This is the kind of place where you could stomp around like you had your own personal wind machine and no one would think twice about it. Beatnik is all about atmosphere, and letting you eat things like veal sweetbread kebabs in a jungle full of tropical plants while a DJ plays. It’s perfect for cocktails, small plates, and pretending you’re on a movie set. Unlike on a movie set, though, you won’t have someone constantly touching up your hair, so thankfully there is no actual tropical humidity.
The crowd at Parlor in the West Loop seems to be more interested in drinking than eating (but the wood-fired pizza is actually pretty good), so this place is actually one of the busiest spots in the neighborhood. It has two patios (one of which is enclosed and heated in the winter) and a very active bar area. So come here if you want a club-like atmosphere for your new hairstyle, but don’t feel like dealing with a bouncer wearing a suit and a well-honed glare.
This River North spot looks like a dive bar, but it has fantastic food, and usually feels like a party. This is the kind of spot you hit up spontaneously after a successful visit to the salon, when you have a great blowout but are still wearing sweatpants. Ideally you’ll also be pretty hungry, because everything from the Nashville hot fried duck livers to the sweet corn rigatoni is great.