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The interior of Parachute restaurant in Chicago, with a long communal table in the middle and seating to each side, one of the city’s best restaurants for a first date.

The Best Restaurants in Chicago for Valentine’s Day

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Valentine’s Day, one of the most romantic days of the year. But the search for a V-Day-worthy restaurant? Not so romantic. When you’re trying to find the right restaurant ambiance (maybe you’re going for super casual or super chic), or the right cuisine (maybe your date likes seafood, or maybe they hate it), things can get stressful very quickly. So to make planning for your big romantic day a little less hectic, here are our picks for the best Valentine’s Day restaurants in Chicago. These 12 eateries will not only impress on February 14th, but on date-night any day of the year.

Find the perfect foodie to dine with on Valentine’s Day, or any other day, on Bumble.

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Parachute

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Husband-and-wife team Johnny Clark and Beverly Kim have been filling seats at this Avondale restaurant ever since they opened doors in 2014 — and that following has only grown in the wake of 2019’s James Beard Awards, when they took home gold for Best Chef: Great Lakes. As such, be sure to book ahead — then be sure to try it all, from baked potato bing bread and smoked yuba ssam to nam prik pao tuna and gochujang cuttlefish. The kitchen’s Asian-American approach extends to the dessert menu, too, with choices like malted matcha tiramisu or Koreapolitan ice cream (a medley of black sesame, yuzu, and red bean).

Courtesy of Parachute

Lost Lake

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When the temperatures drop, there’s nowhere better to be than at Lost Lake. The acclaimed bar, said to be one of the best in the country, will happily transport you to a world of sunshine and tiki cocktails. Take your date on a mini-vacation and sit under a a roof of lauhala as you sip on a rum cocktail, their specialty. Explore tiki cocktails from the early 1940s, like the Fogcutter, or try a more modern interpretation, like the Salty in All the Right Places (with rhum agricole, overproof Jamaican rum, papaya, coconut, lime, salt, and absinthe). And to balance out the drinks, split the grilled chicken wings or green chili dip — or better yet, two po’ boys.

Courtesy of Lost Lake

Young American

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This Logan Square newcomer, has already made a name for itself with its playful menus. The newest transformation at Young American now includes a Filipino food focus, with dishes like the Filipino pimento cheese and the “Not Cacio e Pepe,” made with spicy ramen noodles from Sun Noodle, shiitake stock brewer’s yeast, and chili crisp. The other menu standouts that got all of Chicago talking, though, are the cocktails. Order a spirits-free one, like the pineapple shrub, or, if you’re feeling adventurous, add a CBD tincture to it.

John Stoffer

Old Pueblo Cantina

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Valentine’s Day dates just feel easier in the company of tacos, margaritas, and Latin-inspired music — and bonus points are in order if the spot is brand new. Enter Old Pueblo Cantina, the recently opened restaurant from Ballyhoo Hospitality, the same entertainment aces behind Gemini and Coda di Volpe. Start at the bar with a round of agave-based anything, then head to your table for tastes of queso fundido, red snapper tacos, and chicken tinga enchiladas — followed, of course, by an order of churros y chocolate. Insider tip: Visit again on Mondays, when margaritas are just $5 and are served alongside live tunes from a mariachi band. 

Kira Anderson

Look good with a booking at this always-abuzz restaurant, which continues to be one of the most talked-about tables in town — even several years post-opening. Credit that interest to low-key vibes and heightened fare from chef Jason Vincent, who serves a menu of Midwestern dishes in bold, unexpected ways (from uni shooters and chili salt onion rings to Jonah crab salad and pecan-smoked ribs). Chill out between courses with vinyl-spun sounds from Frank Ocean and Talking Heads and peruse the wine list, a collection of 100-plus offbeat bottles that span the globe. Let sommelier Josh Perlman guide you through pairings, and don’t forget dessert — cajeta ice cream and triple chocolate crostata are standing by. 

Courtesy of Giant

Cafe Robey

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Situated smack-dab in the middle of Wicker Park’s bustling six corners, this neighborhood beacon is easy to find. Once inside, expect to feel the same super-hip energy of the area, thanks to industrial-chic design, an open kitchen, and a score of cool tunes (from Camera Obscura to Harry Nilsson). Chef Kevin McCallister serves a seasonally rotating menu of crowd-pleasing plates that are dialed up just so — a wagyu burger on brioche, short rib pasta, and a sunflower “butter” beet salad, to name a few. Consider them the perfect preamble for dessert, when a maple caramel apple crisp helps to top off a delectable Valentine’s Day dinner.

Adrian Gaut

Spiaggia

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For a V-Day date that is bound to impress, head to this fine dining fixture, where modern Italian cooking, serious service, and epic Mag Mile views have been drawing city dwellers and visitors alike for more than 35 years. The tasting menu is one of the town’s best — though a la carte orders are also top-notch — and (bonus) easier to share. Try the truffle gnocchi, veal tagliatelle, and striped bass, and be sure to request wine pairings from sommelier Rachael Lowe — the list here (700 labels strong) is award-winning. 

Courtesy of Spiaggia

avec Restaurant

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Consider your cool factor heightened upon entry to this lively, industry-beloved restaurant and bar — one of the first spots from the One Off Hospitality team (Blackbird, Big Star, The Publican). Mediterranean-inspired shared plates run the show here and are built for a variety of tastes and appetites: case in point with options like chorizo-stuffed dates, roasted whole fish, and “deluxe” focaccia with taleggio cheese, ricotta, and truffle oil. Match them up with a couple of glasses from their natural-driven wine list, which shines a light on grapes from Greece, Spain, and Portugal.

John Phillip

Cindy's

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For epic city views, energetic crowds, and impressive plates, make a visit to this Mag Mile rooftop, located in the Chicago Athletic Association. Book in advance to bypass a perennial line to the popular post-work spot, which boasts panoramic vistas of some of Chicago’s best sights, from the Jay Pritzker Pavilion and Navy Pier to Lake Michigan and The Bean. Marvel at all of it with a cocktail in hand from beverage director Scotty LoBianco, then settle in for a landslide of chef Christian Ragano’s large format dishes, from pine nut-topped burrata and scallop crudo to mushroom risotto and tenderloin for two. 

Nick Gerber

Mercat a la Planxa

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Sweeping views of Grant Park, bright interiors, and upbeat music welcome guests at this South Loop restaurant, located in the historic Blackstone Hotel. Catalan-inspired cuisine and cocktails are the specialty here, so kick things off with a round of Spanish-style gin and tonics and tapas — namely favorites like bacon-wrapped dates, Iberico ham croquetas, and patatas bravas. Paella portions are sizable (i.e. ripe for sharing). Opt for the Parellada version, with shrimp, clams, sausage, and chicken. A lot of food, yes — but the requisite fuel for the flamenco dancing you’ll crave after two hours spent here. 

Courtesy of Mercat a la Planxa

Virtue Restaurant

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Few restaurants have exploded onto the scene so quickly as Virtue has; the South Side restaurant has racked up awards since its opening a year ago. Virtue exemplifies comfort food at its best and unpretentious service, perfect for setting the mood for a warm and inviting first date. Order the cornbread and mac and cheese to start, then dig into the “large rations,” like the shrimp with grits or the beef short ribs.

Courtesy of Virtue

The Promontory

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Equal parts restaurant and performance space, this Hyde Park hangout boasts all the makings of Valentine’s Day success. Grab tickets to any of the venue’s upcoming acts (from concerts and dance parties to live lit and stand-up), and check out the chef’s counter beforehand. It’s here where the show truly starts, thanks to a brick hearth that readies orders like roasted brussel sprouts, sirloin with roasted broccolini and potatoes, and pork shoulder with smoked mustard sauce. Pair them up with any of the bar’s seasonal sippers, from an apple chia G&T to hot buttered whiskey.  

Find the perfect foodie to dine with on Valentine’s Day, or any other day, on Bumble.

Clayton Hauck for The Promontory
This advertising content was produced in collaboration between Vox Creative and our sponsor, without involvement from Vox Media editorial staff.

Parachute

Husband-and-wife team Johnny Clark and Beverly Kim have been filling seats at this Avondale restaurant ever since they opened doors in 2014 — and that following has only grown in the wake of 2019’s James Beard Awards, when they took home gold for Best Chef: Great Lakes. As such, be sure to book ahead — then be sure to try it all, from baked potato bing bread and smoked yuba ssam to nam prik pao tuna and gochujang cuttlefish. The kitchen’s Asian-American approach extends to the dessert menu, too, with choices like malted matcha tiramisu or Koreapolitan ice cream (a medley of black sesame, yuzu, and red bean).

Courtesy of Parachute

Lost Lake

When the temperatures drop, there’s nowhere better to be than at Lost Lake. The acclaimed bar, said to be one of the best in the country, will happily transport you to a world of sunshine and tiki cocktails. Take your date on a mini-vacation and sit under a a roof of lauhala as you sip on a rum cocktail, their specialty. Explore tiki cocktails from the early 1940s, like the Fogcutter, or try a more modern interpretation, like the Salty in All the Right Places (with rhum agricole, overproof Jamaican rum, papaya, coconut, lime, salt, and absinthe). And to balance out the drinks, split the grilled chicken wings or green chili dip — or better yet, two po’ boys.

Courtesy of Lost Lake

Young American

This Logan Square newcomer, has already made a name for itself with its playful menus. The newest transformation at Young American now includes a Filipino food focus, with dishes like the Filipino pimento cheese and the “Not Cacio e Pepe,” made with spicy ramen noodles from Sun Noodle, shiitake stock brewer’s yeast, and chili crisp. The other menu standouts that got all of Chicago talking, though, are the cocktails. Order a spirits-free one, like the pineapple shrub, or, if you’re feeling adventurous, add a CBD tincture to it.

John Stoffer

Old Pueblo Cantina

Valentine’s Day dates just feel easier in the company of tacos, margaritas, and Latin-inspired music — and bonus points are in order if the spot is brand new. Enter Old Pueblo Cantina, the recently opened restaurant from Ballyhoo Hospitality, the same entertainment aces behind Gemini and Coda di Volpe. Start at the bar with a round of agave-based anything, then head to your table for tastes of queso fundido, red snapper tacos, and chicken tinga enchiladas — followed, of course, by an order of churros y chocolate. Insider tip: Visit again on Mondays, when margaritas are just $5 and are served alongside live tunes from a mariachi band. 

Kira Anderson

Giant

Look good with a booking at this always-abuzz restaurant, which continues to be one of the most talked-about tables in town — even several years post-opening. Credit that interest to low-key vibes and heightened fare from chef Jason Vincent, who serves a menu of Midwestern dishes in bold, unexpected ways (from uni shooters and chili salt onion rings to Jonah crab salad and pecan-smoked ribs). Chill out between courses with vinyl-spun sounds from Frank Ocean and Talking Heads and peruse the wine list, a collection of 100-plus offbeat bottles that span the globe. Let sommelier Josh Perlman guide you through pairings, and don’t forget dessert — cajeta ice cream and triple chocolate crostata are standing by. 

Courtesy of Giant

Cafe Robey

Situated smack-dab in the middle of Wicker Park’s bustling six corners, this neighborhood beacon is easy to find. Once inside, expect to feel the same super-hip energy of the area, thanks to industrial-chic design, an open kitchen, and a score of cool tunes (from Camera Obscura to Harry Nilsson). Chef Kevin McCallister serves a seasonally rotating menu of crowd-pleasing plates that are dialed up just so — a wagyu burger on brioche, short rib pasta, and a sunflower “butter” beet salad, to name a few. Consider them the perfect preamble for dessert, when a maple caramel apple crisp helps to top off a delectable Valentine’s Day dinner.

Adrian Gaut

Spiaggia

For a V-Day date that is bound to impress, head to this fine dining fixture, where modern Italian cooking, serious service, and epic Mag Mile views have been drawing city dwellers and visitors alike for more than 35 years. The tasting menu is one of the town’s best — though a la carte orders are also top-notch — and (bonus) easier to share. Try the truffle gnocchi, veal tagliatelle, and striped bass, and be sure to request wine pairings from sommelier Rachael Lowe — the list here (700 labels strong) is award-winning. 

Courtesy of Spiaggia

avec Restaurant

Consider your cool factor heightened upon entry to this lively, industry-beloved restaurant and bar — one of the first spots from the One Off Hospitality team (Blackbird, Big Star, The Publican). Mediterranean-inspired shared plates run the show here and are built for a variety of tastes and appetites: case in point with options like chorizo-stuffed dates, roasted whole fish, and “deluxe” focaccia with taleggio cheese, ricotta, and truffle oil. Match them up with a couple of glasses from their natural-driven wine list, which shines a light on grapes from Greece, Spain, and Portugal.

John Phillip

Cindy's

For epic city views, energetic crowds, and impressive plates, make a visit to this Mag Mile rooftop, located in the Chicago Athletic Association. Book in advance to bypass a perennial line to the popular post-work spot, which boasts panoramic vistas of some of Chicago’s best sights, from the Jay Pritzker Pavilion and Navy Pier to Lake Michigan and The Bean. Marvel at all of it with a cocktail in hand from beverage director Scotty LoBianco, then settle in for a landslide of chef Christian Ragano’s large format dishes, from pine nut-topped burrata and scallop crudo to mushroom risotto and tenderloin for two. 

Nick Gerber

Mercat a la Planxa

Sweeping views of Grant Park, bright interiors, and upbeat music welcome guests at this South Loop restaurant, located in the historic Blackstone Hotel. Catalan-inspired cuisine and cocktails are the specialty here, so kick things off with a round of Spanish-style gin and tonics and tapas — namely favorites like bacon-wrapped dates, Iberico ham croquetas, and patatas bravas. Paella portions are sizable (i.e. ripe for sharing). Opt for the Parellada version, with shrimp, clams, sausage, and chicken. A lot of food, yes — but the requisite fuel for the flamenco dancing you’ll crave after two hours spent here. 

Courtesy of Mercat a la Planxa

Virtue Restaurant

Few restaurants have exploded onto the scene so quickly as Virtue has; the South Side restaurant has racked up awards since its opening a year ago. Virtue exemplifies comfort food at its best and unpretentious service, perfect for setting the mood for a warm and inviting first date. Order the cornbread and mac and cheese to start, then dig into the “large rations,” like the shrimp with grits or the beef short ribs.

Courtesy of Virtue

The Promontory

Equal parts restaurant and performance space, this Hyde Park hangout boasts all the makings of Valentine’s Day success. Grab tickets to any of the venue’s upcoming acts (from concerts and dance parties to live lit and stand-up), and check out the chef’s counter beforehand. It’s here where the show truly starts, thanks to a brick hearth that readies orders like roasted brussel sprouts, sirloin with roasted broccolini and potatoes, and pork shoulder with smoked mustard sauce. Pair them up with any of the bar’s seasonal sippers, from an apple chia G&T to hot buttered whiskey.  

Find the perfect foodie to dine with on Valentine’s Day, or any other day, on Bumble.

Clayton Hauck for The Promontory

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