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.
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photo credit: Kim Kovacik

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: Eric Wolfinger

Italian

Lakeshore East

$$$$Perfect For:Date NightSpecial OccasionsBirthdaysSee And Be SeenDrinking Good CocktailsDrinking Good Wine
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Not every romantic outing needs to be a “whole thing”—but when you are trying to make it a “whole thing,” check out Tre Dita in Lakeshore East. First off, this Italian restaurant from the chef behind hyped-up spots like LA’s Funke is in the St. Regis Hotel, so dining in a five-star hotel where a room costs $800 already makes a statement. But even if you don’t plan on booking a room, eating incredible housemade duck ragu pappardelle and drinking excellent Italian wine next to a gorgeous view of the river feels nothing short of luxurious.

photo credit: Kim Kovacik

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Anelya’s playful space with flower-shaped neon lamps and sparkly zakusky carts is perfect for a unique and exciting date night, whether it’s your first or you stopped counting years ago. And the food at this intimate Avondale spot is just as exciting. Don’t be surprised if, mid-conversation, you start reflecting on how the incredible trout roe tarts cram the essence of a lox bagel into a tiny pastry. Throw in some pours of boozy housemade piana vishnya, plus a very Shazammable European synthpop soundtrack, and you’ve got everything you need for a fun night.

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Provaré in West Town is a guaranteed great time regardless of why you’re here, date night is no different. Their Creole-Italian dishes—cheesy chicken parm, crispy fried lobster tails with spicy aioli, and spinach artichoke dip—are so rich and comforting you’d probably still leave in a good mood even if the date ends up being a bust. The Chicago-themed cocktails are also delicious, like the refreshing Hyde Park with tequila, pineapple juice, and midori. And since there’s always an excellent R&B and hip-hop throwback playlist, instead of asking your date for their MBTI, you can figure out what their favorite Ashanti-Ja Rule collab says about them.

When your ideal date night involves a few excellent pours of fermented grapes, head to Easy Does It in Logan Square. It’s unpretentious and casual, so even if you have no clue what "terroir" is, it’s still a fun place to drink and hang. They have a fantastic wine selection, with approachable descriptions like “It’s Clementime” or “Earth Jam.” Easy Does It has plenty of seating whether you’re a table and booth person, or would rather sip on orange wine while sinking into a comfy chair. Weekdays are a bit more relaxed with occasional live jazz, but if dancing is also part of your ideal date, come for a late-night weekend DJ set.

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Atta Girl is a bar and bistro that's good for charcuterie and wine for a first date, or getting the excellent burger with smoked tomato jam if you make it to round two. Their menu is vaguely French, and the dimly lit space makes everyone look exponentially more attractive whether they're sitting at the bar or snuggled up in a big leather booth. If your date is easily wooed by poultry in sexy lighting, their plate of half a smoked duck with a dollop of pâté sitting on fluffy fries can help.


The Meadowlark’s dark wooden interior and comfy leather couches are handy when your local dive’s sticky floors and “aged” keg of PBR don't exactly register as date-night material. All of the cocktails at this Logan Square bar are well-made and part of a themed menu (past themes have been birds and the Chicago World's Fair). Plus, they also have a short menu of tasty small plates like smoky grilled jerk chicken hearts or turkey empanadas made with bacon fat pastry. And it’s no surprise that the food is delicious since The Meadowlark comes from the same team behind Union, also on this list.


Between its catchy funk and soul soundtrack, delicious food, and long wine list, Bronzeville Winery is an ideal date night spot. This American restaurant also 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 good, creative dishes like the steak tartare with shio kombu and a surprisingly delicious foie gras taco. And while the dining room is filled with white tablecloths and looks like a Swiss chalet, it's not stuffy—the space is busy and upbeat thanks to friendly servers and an energetic hip-hop soundtrack.


Union is the neighboring sister restaurant of The Meadowlark (also on this guide), but while The Meadowlark is a cocktail bar with only a few small bites, Union really wants to feed you. The fantastic 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.

If you've ever wanted 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, great service, and fantastic 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, Armitage Alehouse has the ability to suck you in and magically make you forget that the world is spinning outside.


Alla Vita in the West Loop is always buzzing with staff, and everyone from couples to small groups. And the space—with hanging plants and a very cool fabric wave ceiling—is roughly the size of Terminal 2 at O’Hare but with way better food. The menu at this Italian spot isn’t going to blow your mind with creativity (it’s mainly pizza, pasta, and a handful of entrees), but 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 ideal for a date when 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. The seared duck salad and incredibly crispy egg rolls are excellent starters, while the phở and bone marrow fried rice are fantastic entree choices.


This Portage Park bar has great cocktails and tasty food. Moonflower has creative options like the Kiss & Tell (tequila, mezcal, and Korean soda) along with classics like Manhattans. Their menu also has stuff like pork dumplings and a double patty burger. The space is dimly lit and full of plants, which will give you an excuse to talk about how much you love Little Shop Of Horrors. And if you want a change of scenery without having to travel too far, head to their equally good basement speakeasy, Nightshade.

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