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The Most Romantic Date Ideas For Valentine's Day in Chicago
The Most Romantic Date Ideas For Valentine's Day in Chicago

The Most Romantic Date Ideas For Valentine's Day in Chicago

The most romantic restaurants and date ideas to celebrate Valentine's Day all February long in Chi-Town. 💘


Published January 13, 2023

Valentine's Day is around the corner, and thankfully the Windy City has all the ingredients you need to get the sparks flying with dazzling city lights, Michelin-starred restaurants, and dreamy waterfront spots to explore and admire. Whether you're looking for the perfect romantic restaurant, want to shake things up with comedy or a show, or want something a little more lowkey, our list of romantic date ideas has something for everyone.

Not feeling Valentine's Day this year? Check out this Bad Blood Break-Up Bar, where you can drink, sing, and dance along to Taylor classics. Valentine's Day is also a good excuse to gather the crew and treat yourselves to an epic group dinner. Or, go to a Galentine's Day Brunch Party at Gold Coast.

12 Romantic Ways to Spend Valentine's Day in Chicago

Learn to make Valentine's Cocktails

Learn to make Valentine's Cocktails

Join Gold Coast Social and its top mixologists for a special Valentine's Day-themed experience. The spot will be decked out in Valentine's Day decor, and you'll get to create two different cocktails. When you've finished, enjoy sipping them together with Valentine's Day-themed flatbread.

Where: 7 W Division St, Chicago, IL
For more information on Love at First Sip Cocktail Class.

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location_on Gold Coast Social, CHI

Love At First Sip Cocktail Class

$55
  • event 2023-01-26
book

Join Gold Coast Social and its top mixologists for a special Valentine's Day-themed experience. The spot will be decked out in Valentine's Day decor, and you'll get to create two different cocktails. When you've finished, enjoy sipping them together with Valentine's Day-themed flatbread.

Where: 7 W Division St, Chicago, IL
For more information on Love at First Sip Cocktail Class.

See a Live Show at a Hidden Speakeasy

See a Live Show at a Hidden Speakeasy

Few things feel sexier than slipping into a hidden speakeasy. Bordel is a cocktail bar and cabaret inspired by the sultry energy of Paris’ Pigalle and Montmartre. You and your date will make your way through the hidden door and up the leopard print stairs and find yourselves inside a plush candlelit lounge complete with pink velvet sofas and curtains, tasseled chandeliers, and ornate bronze sconces.

Enjoy surprising cocktails along with nightly entertainment that includes a premier cast of jazz musicians, burlesque performers, flamenco artists, magicians, cabaret dancers, and DJ performances.

Where: 1721 W Division St., Chicago, IL
For more information on Bordel and Chicago Speakeasies.

Few things feel sexier than slipping into a hidden speakeasy. Bordel is a cocktail bar and cabaret inspired by the sultry energy of Paris’ Pigalle and Montmartre. You and your date will make your way through the hidden door and up the leopard print stairs and find yourselves inside a plush candlelit lounge complete with pink velvet sofas and curtains, tasseled chandeliers, and ornate bronze sconces.

Enjoy surprising cocktails along with nightly entertainment that includes a premier cast of jazz musicians, burlesque performers, flamenco artists, magicians, cabaret dancers, and DJ performances.

Where: 1721 W Division St., Chicago, IL
For more information on Bordel and Chicago Speakeasies.

Share Fondue by the Fire at Geja’s Cafe

Share Fondue by the Fire at Geja’s Cafe

There are romantic dinners, and then there’s dining at Geja's. One of Chicago's most romantic restaurants is serving up a Valentine's Day Special that includes an appetizer of Swiss Gruyere cheese fondue with assorted breads, vegetables, and fruits for dipping, and an entree of Beef Tenderloin, Australian Lobster Tail, and Gulf Shrimp. Top it all off with Geja’s Belgian Chocolate fondue flamed tableside and served with marshmallows for roasting.

Where: 340 W Armitage Ave., Chicago IL 60614
For more information on Geja's Cafe.

There are romantic dinners, and then there’s dining at Geja's. One of Chicago's most romantic restaurants is serving up a Valentine's Day Special that includes an appetizer of Swiss Gruyere cheese fondue with assorted breads, vegetables, and fruits for dipping, and an entree of Beef Tenderloin, Australian Lobster Tail, and Gulf Shrimp. Top it all off with Geja’s Belgian Chocolate fondue flamed tableside and served with marshmallows for roasting.

Where: 340 W Armitage Ave., Chicago IL 60614
For more information on Geja's Cafe.

Laugh the Night Away at a Stand-Up Comedy Show

Laugh the Night Away at a Stand-Up Comedy Show

Who said romance has to be boring? Laugh off any date night jitters at a fun comedy show featuring today's biggest names. On February 14, Laugh Factory will host a Valentine's special, and the world-famous stage will be transformed to reflect the holiday of love. These local comedians will deliver something for every taste and style of comedy, and many of the greats have come through the city!

Where: Laugh Factory: 3175 N Broadway, Chicago, IL 60657
For more information on Stand Up Comedy Tickets.

location_on Laugh Factory, CHI

Stand Up Comedy Tickets

From$20 $15 25% off
  • event 2022-06-01
book

Who said romance has to be boring? Laugh off any date night jitters at a fun comedy show featuring today's biggest names. On February 14, Laugh Factory will host a Valentine's special, and the world-famous stage will be transformed to reflect the holiday of love. These local comedians will deliver something for every taste and style of comedy, and many of the greats have come through the city!

Where: Laugh Factory: 3175 N Broadway, Chicago, IL 60657
For more information on Stand Up Comedy Tickets.

Sip Champagne at 3 Arts Club Cafe

Sip Champagne at 3 Arts Club Cafe

This posh restaurant is inside the Restoration Hardware store, but don’t let that fool you into thinking this place doesn’t ooze romance. The stunning interior is located in the atrium and is surrounded by glowy lights and glass, creating the perfect moody ambiance for a romantic date night. Choose a bottle from their lengthy wine list, and you’re on your way to having an unforgettable evening. 

Where: 1300 N Dearborn St., Chicago, IL
For more information on 3 Arts Club Cafe.

This posh restaurant is inside the Restoration Hardware store, but don’t let that fool you into thinking this place doesn’t ooze romance. The stunning interior is located in the atrium and is surrounded by glowy lights and glass, creating the perfect moody ambiance for a romantic date night. Choose a bottle from their lengthy wine list, and you’re on your way to having an unforgettable evening. 

Where: 1300 N Dearborn St., Chicago, IL
For more information on 3 Arts Club Cafe.

Explore a Museum or Gallery Together

Explore a Museum or Gallery Together

There's something so charming about wandering through a museum, exploring art, and learning something new together. The Art Institute is a classic and offers world-class art, plus some dreamy spots like the Tiffany window. Head to Adler Planetarium and look to the stars to see if you and your date are meant to be, or explore the various art galleries of River North.

P.S. See our list of free and discounted museum days here.

Where: Various locations.

There's something so charming about wandering through a museum, exploring art, and learning something new together. The Art Institute is a classic and offers world-class art, plus some dreamy spots like the Tiffany window. Head to Adler Planetarium and look to the stars to see if you and your date are meant to be, or explore the various art galleries of River North.

P.S. See our list of free and discounted museum days here.

Where: Various locations.

Take a Cooking & Cocktails Class Together

Take a Cooking & Cocktails Class Together

If you want something a little more interactive than just dinner, try taking a cooking class together, where you can learn a new skill and enjoy delicious food. Cozy up with your date at the Fairmont Lodge’s Cooking & Cocktail Classes. From 6:00 pm to 8:00 pm, learn how to make popular dishes and cocktails from Fairmont Chicago’s team of talented chefs and local mixologists. Each class will center around how to make favorites, including an inspired cocktail (with a recipe included so you can make it at home), fresh pappardelle pasta, and a celebratory cheese and charcuterie board.

Where: 200 N Columbus Dr, Chicago, IL
For more information on Cooking & Cocktails Classes.

If you want something a little more interactive than just dinner, try taking a cooking class together, where you can learn a new skill and enjoy delicious food. Cozy up with your date at the Fairmont Lodge’s Cooking & Cocktail Classes. From 6:00 pm to 8:00 pm, learn how to make popular dishes and cocktails from Fairmont Chicago’s team of talented chefs and local mixologists. Each class will center around how to make favorites, including an inspired cocktail (with a recipe included so you can make it at home), fresh pappardelle pasta, and a celebratory cheese and charcuterie board.

Where: 200 N Columbus Dr, Chicago, IL
For more information on Cooking & Cocktails Classes.

Share a Heart Shaped Pizza

Share a Heart Shaped Pizza

If you want to avoid the dinner crowds, but still want to share a romantic evening together, there's always the forever favorite heart-shaped pizza. Plan a night in and queue up a classic rom-com or your favorite romantic film, light some candles, and bust out some wine or bubbly to enjoy with your festive pizza. Order Valentine's Dinner for Two from Sfera, offering appetizers, salads, a heart-shaped Sfincione, two cannoli, and cocktail bases to mix up your own drinks at home. Or, surprise your partner with their favorite pizza in the shape of a heart from Robert's (you can even get an ice cream heart pizza!).

Other restaurants offering a heart-shaped pizza (both in-person and for delivery) include Bartoli's, Lou Malnati's, Giordano's, Eataly, Homeslice, and Dimo's.

Where: Various locations.

If you want to avoid the dinner crowds, but still want to share a romantic evening together, there's always the forever favorite heart-shaped pizza. Plan a night in and queue up a classic rom-com or your favorite romantic film, light some candles, and bust out some wine or bubbly to enjoy with your festive pizza. Order Valentine's Dinner for Two from Sfera, offering appetizers, salads, a heart-shaped Sfincione, two cannoli, and cocktail bases to mix up your own drinks at home. Or, surprise your partner with their favorite pizza in the shape of a heart from Robert's (you can even get an ice cream heart pizza!).

Other restaurants offering a heart-shaped pizza (both in-person and for delivery) include Bartoli's, Lou Malnati's, Giordano's, Eataly, Homeslice, and Dimo's.

Where: Various locations.

Experience a Fancy Tasting Menu

Experience a Fancy Tasting Menu

Esmé is a fine dining restaurant founded by a husband and wife pair of culinary experts and located in Lincoln Park. Featuring artfully crafted dishes, this special spot will offer a Valentine's Day tasting menu that showcases luxurious dishes and ingredients like white truffles, burnt onion consommé, white sweet potato ice cream, osetra caviar return, and more. At Bar Esmé (located within the same space), diners can select a four-course menu for $150.00 per person. Menu items include Duck Ravioli, Monk Fish a la Normandie, Wagyu Au Poivre, and more.

P.S. As if the indulgent menu and husband and wife duo aspect weren't enough, Esmé translates to "beloved" in French, putting this date night spot off the charts in the romance category.

Where: 2200 N. Clark St, Chicago, IL
For more information on Esmé and bar Esmé.

Esmé is a fine dining restaurant founded by a husband and wife pair of culinary experts and located in Lincoln Park. Featuring artfully crafted dishes, this special spot will offer a Valentine's Day tasting menu that showcases luxurious dishes and ingredients like white truffles, burnt onion consommé, white sweet potato ice cream, osetra caviar return, and more. At Bar Esmé (located within the same space), diners can select a four-course menu for $150.00 per person. Menu items include Duck Ravioli, Monk Fish a la Normandie, Wagyu Au Poivre, and more.

P.S. As if the indulgent menu and husband and wife duo aspect weren't enough, Esmé translates to "beloved" in French, putting this date night spot off the charts in the romance category.

Where: 2200 N. Clark St, Chicago, IL
For more information on Esmé and bar Esmé.

Go for a Wine Tasting at Uvae Kitchen & Wine Bar

Go for a Wine Tasting at Uvae Kitchen & Wine Bar

Spend an afternoon sipping wines at Uvae Kitchen & Wine Bar in Andersonville. Uvae will offer a Valentine’s-themed wine tasting featuring “Sweetheart Wines” at the adjacent Fromagerie & Tasting Room on Saturday, February 11, at 3 pm. Guests will explore the holiday's history with four 4-ounce wine pours, plus small bites like Duck Pâté and a cheese plate.

For a grander Valentine's Day experience, Uvae will offer a 5-course Valentine’s Day Wine Pairing Dinner that will include Oysters three ways, Lobster Bisque, King Salmon, and a Petite Filet. Dessert will feature a white chocolate Soufflé with white chocolate, strawberry crème anglaise, biscoff, and meringue.

Where: 5553 N. Clark St. Chicago, IL
For more information on Uvae.

Spend an afternoon sipping wines at Uvae Kitchen & Wine Bar in Andersonville. Uvae will offer a Valentine’s-themed wine tasting featuring “Sweetheart Wines” at the adjacent Fromagerie & Tasting Room on Saturday, February 11, at 3 pm. Guests will explore the holiday's history with four 4-ounce wine pours, plus small bites like Duck Pâté and a cheese plate.

For a grander Valentine's Day experience, Uvae will offer a 5-course Valentine’s Day Wine Pairing Dinner that will include Oysters three ways, Lobster Bisque, King Salmon, and a Petite Filet. Dessert will feature a white chocolate Soufflé with white chocolate, strawberry crème anglaise, biscoff, and meringue.

Where: 5553 N. Clark St. Chicago, IL
For more information on Uvae.

Take a Pizza Making Class and Sip Wine

Take a Pizza Making Class and Sip Wine

Spend a romantic evening making handmade Neopolitan pizzas and sipping on your choice of beer and wine at this DIY Pizza and sip class at Millennium Hall. Choose from a number of toppings, sauces, meats, and cheeses, and then make a selection from the open bar while you enjoy some quality conversation and one-on-one time. When the pizza is ready, you can choose to take it home or indulge together at the restaurant.

Where: Millennium Hall: 11 N Michigan Ave, Chicago, IL 60602
For more information on DIY Pizza and Sip.

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location_on Millennium Hall, CHI

DIY Pizza and Sip

$55
  • event 2022-11-01
book

Spend a romantic evening making handmade Neopolitan pizzas and sipping on your choice of beer and wine at this DIY Pizza and sip class at Millennium Hall. Choose from a number of toppings, sauces, meats, and cheeses, and then make a selection from the open bar while you enjoy some quality conversation and one-on-one time. When the pizza is ready, you can choose to take it home or indulge together at the restaurant.

Where: Millennium Hall: 11 N Michigan Ave, Chicago, IL 60602
For more information on DIY Pizza and Sip.

Attend a Beauty and the Beast Cocktail Experience

Attend a Beauty and the Beast Cocktail Experience

Is anything more romantic than a literal fairytale love story? Gift your Valentine tickets to this immersive cocktail experience that's an escape room, a theater show, and an adventure all blended into one. Based on the Jeanne-Marie Leprince de Beaumont fairytale, guests are invited to come along on a 90-minute journey and step into the enchanted and cursed world of Beauty & The Beast. Dress up in your most elegant Victorian-inspired costumes and enjoy crafting two bespoke-themed cocktails, solving riddles and challenges, and more!

Where: Esmerelda's Lounge: 2539 W Division St., Chicago, Illinois 60622
For more information on Beauty and the Beast Cocktail Experience.

location_on Esmerelda's Lounge, CHI

Beauty And The Beast Cocktail Experience

$45
  • event 2022-09-07
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Is anything more romantic than a literal fairytale love story? Gift your Valentine tickets to this immersive cocktail experience that's an escape room, a theater show, and an adventure all blended into one. Based on the Jeanne-Marie Leprince de Beaumont fairytale, guests are invited to come along on a 90-minute journey and step into the enchanted and cursed world of Beauty & The Beast. Dress up in your most elegant Victorian-inspired costumes and enjoy crafting two bespoke-themed cocktails, solving riddles and challenges, and more!

Where: Esmerelda's Lounge: 2539 W Division St., Chicago, Illinois 60622
For more information on Beauty and the Beast Cocktail Experience.

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