CHIGuide

Where To Go On A Date Right Now In Chicago

You might need some help choosing a date spot in Chicago. So we put them all in one place for you.

Where To Go On A Date Right Now In Chicago   guide image

photo credit: Clayton Hauck

Scheduling date nights is crucial at any stage of a relationship. From that pivotal first outing with a friendly stranger to the 251st dinner with your soulmate, date spots should always feel just a little bit special. So whether you’re trying to impress a potential partner with a low-key bar or agreeing to give your joint Seamless account the night off, use this guide to find the perfect date spot to suit your needs in Chicago right now.

THE SPOTS

photo credit: Kim Kovacik

Bronzeville Winery review image
8.0

Bronzeville Winery

Between its fantastic funk and soul soundtrack, delicious food, and long wine list, Bronzeville Winery is an ideal date night spot. Plus, this American restaurant in Bronzeville has a great sidewalk patio, and we can't think of a better way to spend an evening than listening to Earth Wind & Fire with some caramelized watermelon with a glass of pinot grigio.


Obelix is located in a quieter part of River North where you can have an upscale date night in relative serenity. It's a French spot from the same team as Le Bouchon, and they have a fusion-y menu with creative dishes that actually taste good—like steak tartare with shio kombu and a surprisingly delicious foie gras taco. And while the dining room is filled with white tablecloths and looks a little like a Swiss chalet, it's not stuffy– the space is busy and upbeat thanks to friendly servers and an energetic hip hop soundtrack.


If you don’t want to commit to a full dinner (but still want the option) meet someone for drinks at Mother’s Ruin in Avondale. This casual cocktail bar has reasonably priced cocktails and tasty snacks like pimento cheese with fried saltines, wings, and a smoky eggplant dip. The food is way better than it needs to be, the cocktails are all $12, and the space is busy without feeling chaotic. Plus the kitchen is open until at least 2am just in case after the date ends you want to circle back and order a cheeseburger by yourself.


Aikana review image
7.7

Aikana Chicago

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Dinner at Aikana in the West loop might make you forget that we live in a city that necessitates owning a floor-length puffer coat. This upscale Latin American restaurant is filled with hanging basket lights and tropical plants, and the menu focuses on food from Central and South America. You’ll find dishes like lime-cured wagyu on top of a crispy rice cake, mote and chorizo mixed with an incredible poblano salsa, and the churrascaria, which includes your choice of meat, tubers, arepas, and a few other sides that are perfect for two people to share.


Union is a bar where you can get a fantastic dinner to go with your drinks. It’s the sister restaurant of Lardon (which is also on this guide). While Lardon is a salumeria specializing in meat and cheese boards, Union really wants to feed you. The dishes here all have little twists that make them stand out from the usual pub food suspects— like lightly breaded fried olives filled with mortadella, or juicy lamb and pistachio meatballs swimming in a caper salsa verde. To remind us that this is a bar, they have a long whiskey list, which they use to make a variety of creative Old Fashioneds.


Complex salsas, handmade corn and flour tortillas, and some of the best palomas in Chicago are just a few of the reasons why we like Con Todo as a date spot. This Mexican restaurant's bright space has an open kitchen, lots of tables for couples, and a large bar that’s responsible for making the aforementioned palomas. The menu has small plates like smoky tatemada with fresh chips, tacos, tortas (the “pamburgesa” is a fun hybrid of a spicy pambazo and a smashburger), and dinners like the tamal frito: a corn panisse with sweet roasted squash, savory mushrooms, and a rich pipian verde.


A bunch of new Italian restaurants have recently opened in Chicago, but Segnatore is the best for a casual date night. The Humboldt Park restaurant has the vibe of a European cafe, and is busy—filled with people laughing and probably pretending they’re on vacation. But the main reason we love this place is because of the excellent food. Every dish has some kind of creative twist that makes it interesting. The meatballs are filled with melted scamorza, offering the benefits of a Juicy Lucy without the risk of third-degree burns. Their “lasagna” is deconstructed into a pile of handmade garlic mafaldine, whipped ricotta, and a mushroom bolognese that would win in a steel cage death match against any meat version. We can’t promise that your date will be impressive, but your meal here definitely will be.


If you want to have a date in the parlor of the Clue mansion, head to Armitage Alehouse in Lincoln Park. It’s from the Bavette’s team, and has a 1920s jazz playlist, a dim dining room filled with old-timey artwork, fringed lampshades, fantastic service, and great food. The menu has dishes like steak tartare, lamb chops, plus a selection of incredible pot pies (like pheasant and foie gras). Between the prohibition-era soundtrack and windowless space, this place has the ability to suck you in and magically make you forget that the world is spinning outside.


The Lardon is a salumeria, so the menu is full of salumi, cheese, and various meats they cure in-house. Basically a bunch of fun, snack foods that are perfect for a casual date. Sit out on their patio, order a meat and cheese spread (which come with housemade accouterments like onion jam), some wine, and wave a cornichon around to emphasize a hilarious-yet-charmingly-relatable point you’re making.


photo credit: Kim Kovacik

Dear Margaret    review image
8.3

Dear Margaret

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If you’re looking for a leisurely spot where you can talk about your traumatic childhoods and/or plan a vacation together, book a table at Dear Margaret in Lincoln Park. This charming French-Canadian restaurant in Lincoln Park has wonderful dishes like foie gras terrine with fluffy milk bread, duck breast with lentils, and a friendly team who will leave you alone while you get to the bottom of why the 28 on your ACT disappointed your dad.


Alla Vita in the West Loop is always buzzing with staff, and everyone from couples to small groups. And the space is impressive— decorated with hanging plants and a very cool fabric wave ceiling. Plus, it’s roughly the size of Terminal 2 at O’Hare but with way better food. This Italian spot is from the same chef as Boka, and while the menu isn’t going to blow your mind with creativity (it’s mainly pizza, pasta, and a handful of entrees) it is delicious. The cacio e pepe ricotta dumplings can only be described as “sexy”, the pizza has a chewy crust, and the chicken parmesan stays crispy even while sitting in a rich tomato sauce.


This Vietnamese restaurant is perfect for a date where you are 100% confident eating in natural lighting. Sochi has garage-style windows that brighten up the large dining room, and the space is nice but won’t make you feel underdressed. Plus, the food is really good. There are options like a refreshing seared duck salad that’s delicious. There’s also a great bánh mì (which had an excellent ratio of pâté and pork loaf to crunchy bread), and bigger entrees like phở and cơm chiên. And after being BYOB for months, they now serve cocktails, wine, and beer.


Is hot pot a good date food? It depends on the spot, and when it comes to Qiao Lin, we’re going to say yes. For one thing, this restaurant in the 88 Marketplace building has tables designed for just two people. And the menu has suggested cooking times, which is not only helpful, but can help avoid potential arguments about how long you should leave the fish balls in the spicy broth (five minutes, by the way). Plus, you can order pots with either one, two, or three-way broth dividers, which is a really good way to gather intel about important topics like sharing, and three-ways.


Provaré is a bright Creole and Italian spot in West Town with an R&B playlist that will make you realize how much you enjoy ’90s Usher. It’s a fun spot—you’ll get complimentary shots of one of their house cocktails as soon as you sit down. The menu is short (just a few appetizers and mains), but really good. Standout dishes include cheesy spinach and artichoke dip filled with shrimp and crawfish, shrimp Hennessy scampi, and bone-in lamb chops with corn maque choux. Oh, and in case you didn’t read your date’s profile carefully, they have a couple of vegan options, too—like Impossible Meat bolognese and brussels sprouts topped with vegan parmesan.


The Duplex in Logan Square serves food from different chefs every six months, and (to us) feels more like a bar with great food than a restaurant. That’s partially because of the great music, long cocktail list, and literal bar which takes up half the (pretty large) restaurant. But also because of how you order the food: from a QR code at the table, and then you just close out your tab whenever you’re done. Right now they're serving food from a Latin American restaurant called Cacahuates, and Mediterranean from Kalista.



This is a new cocktail bar in Portage Park with great drinks and tasty food. Moonflower has creative options like the Seeing Green (matcha, condensed milk, soju, and vodka) along with classics like Manhattans. Plus, they have also have stuff like fries topped with bolognese, grilled cheese and tomato soup, and patty melts. The space is dimly lit and full of plants, which will give you talking points about all the pandemic houseplants that kept you company during quarantine.


This new cocktail bar in Humboldt Park is versatile. It has both a cute indoor and outdoor space. There’s a cozy wood-burning fireplace inside, and a large partially-covered heated patio. The menu is divided into “hi” (with strong, boozy cocktails) and “lo” (lower ABV options for when you don’t want to get accidentally drunk). Unlike a lot of Chicago bars, Hi-Lo is open seven days a week, and on Friday through Mondays it opens at 2pm. In the afternoon it feels like a coffee shop (but for booze—there is no coffee on the menu). At night the crowd is a little livelier, though you’ll still get the impression that it’s filled primarily with the kind of laid-back people who host game nights. Which is fine by us.


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