The season of love is right around the corner and now is the time to plan the perfect Valentine’s Day celebration. Here’s 10 of the best spots to drink, dine, and relax in Chicago this holiday.
Photo/Josh Ohms – Navy Pier
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Staff Writer
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January 28, 2026
Valentine’s Day is almost here and there’s a good chance you’re finalizing your day-of plans here in Chicago.
Whether you’re looking for a romantic dinner destination, a low-key cocktail spot, or the perfect date night experience, there’s plenty going on in the Windy City.
Here’s your guide to the best things to do this Valentine’s Day in Chicago.
Valentine’s Day Dinner for two at Art Smith’s Reunion
Photo/Art Smith’s Reunion via Facebook
Celebrate Valentine’s Day with a romantic prix fixe dinner for two at Art Smith’s Reunion on Saturday, February 14. The all-inclusive menu features a full five courses: Crab Cakes, Steak Frites, Herbed Scallops, a “Love Goddess” cake and sparkler, plus a chocolate martini.
Heart-shaped sushi at Sunda
Sunda New Asian is opening its doors to guests this Valentine’s, offering a host of à la carte specials including heart-shaped sushi! Other specials include Lobster Lo Mein, oysters with caviar, and a decadent ube pie.
Valentine’s Day specials at Olio e Più
Photo/Olio e Più
Beloved River North trattoria Olio e Più is debuting several limited-time dishes this Valentine’s Day, in addition to it’s à la carte menu. Specials include beef tartare with housemade giardiniera, burratta with basil pesto, and beef filets with fig and gorgonzola.
Valentine’s Day couple’s dinner at The Grillroom
Photo/The Grillroom Chophouse and Wine Bar
Enjoy a $150 four-course prix fixe dinner for two at The Grillroom Chophouse and Wine Bar this Valentine’s Day. Guests can choose from a Mini Charcuterie Board, Wedge Salad, Filet Mignon, Lamb Chops, Red Velvet Cake, and other chef-curated selections. Add a wine pairing for just $25.
Prix Fixe steak dinner at Perry’s Steakhouse
Source/Perry’s
Perry’s Steakhouse is offering an indulgent 3-course prix fixe Valentine’s dinner starting at just $79 per person. Specials include lobster bisque, prime ribeye, Perry’s Famous Pork Chop, New York strip, white chocolate cheesecake, and more.
Lover’s Karaoke Night at Central Park Bar
Source/Central Park Bar
Enjoy a fun night out this Valentine’s Day at Avondale’s Central Park Bar. Start the evening off with a half-price happy hour from 4-7 p.m., followed by karaoke until 11 p.m. Drink specials include the “Avondale Kisses” cocktail with strawberry and chocolate liqueurs.
Estelle’s Tattoo Night and Valentine’s Day Bash
Photo/Estelle’s
Chicagoans can get a permanent symbol of love at Estelle’s tattoo night. Artists from local Rocket Tattoo will be on site Wednesday, February 11, from 9 p.m. til 3 a.m. with tattoos starting at just $50. Guests will also enjoy special craft cocktails like the Spritzy Spritz with apricot liqueur and sparkling wine. On February 14, come by to dance and drink all night long with Estelle’s Valentine’s Day Bash.
Valentine’s Day Celebration at The Getaway
Photo/The Getaway
The Getaway in Lincoln Square is where cozy ambiance meets fun late night energy this Valentine’s Day. The favorite local cocktail lounge is offering $9 beer and shot combos and $14 cheese boards on February 14, plus a fun-filled DJ dance party and DIY craft making all night long.
Valentine’s Day Happy Hour & Late-Night DJ Set at aliveOne
Photo/aliveOne
aliveOne in Lincoln Park is the place to be for relaxed vibes and bargain drinks this Valentine’s Day. The neighborhood bar is offering a half-price happy hour from 4-6 p.m. with cocktail specials galore. As the night rolls on, guests will enjoy a late-night DJ set from 10 p.m. – 2 a.m.
Valentine’s Fireworks and Tunnel of Love at Navy Pier
Source/Navy Pier
Navy Pier is your one-stop destination this Valentine’s Day for unforgettable events. This year, visitors will take in a special Valentine’s firework show on February 14. Be sure to stop by the Tunnel of Love for some amazing photo ops, or take a ride on the Centennial Wheel.