How to Spend Valentine’s Day 2026 in Chicago

On the Magnificent Mile, Labriola puts a literal spin on the adage about the way to a person’s heart being through their stomach. On Feb. 12^th, they’ll have a heart-shaped pizza-making night ($65/person) that includes a welcome cocktail, spritzes and wine, appetizers, and tiramisu.

By Dave Lifton (@daveeatschicago)

Labriola’s pies are thin-crust, so deep-dish lovers should consider the similar event at the spot where it was invented. Pizzeria Uno and Due’s class ($158/couple, several timeslots from Feb. 12^th-14^th) comes with an appetizer, salad, champagne and another drink, and dessert. 

Another Chicago institution, Garrett Popcorn Shops, has unveiled a new flavor—white chocolate strawberry—available at all of its shops through Valentine’s Day.  You can get it in a tin with pink stripes and choose from one of three Valentine’s-themed lid decals. 

If those heart-shaped boxes of assorted chocolates at the drugstore seem too overdone, go to Lakeview’s Windy City Sweets. There, you’ll find more than 1,200 sweets, including chocolate-covered fruits, nuts, and pretzels; handmade fudge, gummi candies; plus gift baskets and customizable tins. 

Fulton Market’s Lyra is offering a special four-course tasting menu ($129/person) on Valentine’s Day that spotlights its modern approach to Greek cuisine. Enjoy dishes like charred octopus, spanakopitakia, halloumi souvlaki, zucchini and eggplant, wild Alaskan halibut, and lamb chops, with dark chocolate tart or portokalopita for dessert. Wine with each course is available for $49/person. 

Make your commitment to your partner permanent on Feb. 11^th at Estelle’s in Wicker Park. That night, they’ll have a tattoo artist on-site inking customers for $50. The vibe gets a little sweeter three nights later, when they’ll have a Valentine’s Day card-making station. 

Inspired by contemporary Spanish flavors, West Town’s Mama Delia’s Valentine’s Day dinner ($45/person) is designed for sharing with your loved one. Start by choosing two of five tapas, move onto one of four entreés, and finish with flan or churros with chocolate sauce. The dinner is offered Feb. 12^th-14^th. 

Enjoy a romantic dinner on the water with City Cruises’ Valentine’s Premier Plus Dinner Cruise on the Chicago River. The Silver Package ($237/person) comes with a single rose and a champagne toast, and the Gold and Silver Packages add more drinks and a half-dozen roses. 

Or you can see Chicago from the air thanks to Fly Heli’s helicopter tour ($215/person). The 16-mile trek soars over all the major downtown sites, and kicks off with a champagne toast. 

Budding mixologists can head to Industry Ales in the Loop and take a cocktail class ($50/person, $90/couple). Over the course of the two hours, you’ll learn to make three drinks, then create your own in a competition with the other attendees for the chance to win a prize. A 10 oz. beer and small bites are included, and those wishing to dine at the restaurant will receive 10% off the bill. 

At Beverly’s Wild Blossom Meadery & Winery, the Valentine’s Winemaking Experience and Dinner on Feb. 14^th ($159/person, $175 as the event gets closer) begins with you and your partner creating a customized blend of wine from the winery’s selections that you’ll be able to take home. That’s followed by a dinner paired with meads for extra sweetness. To add a bit of whimsy, there’s also a grape-stomping contest. 

It’s not quite that fancy at Central Park Bar. On Feb. 14^th, the Avondale watering hole has a half-price happy hour from 4 – 7 PM, followed by “Lover’s Karaoke Night.” They’ve created the Avondale Kisses cocktail, which includes strawberry and chocolate liqueurs, and will have complimentary Valentine’s candy all night. 

For a staycation, consider the historic Palmer House Hilton. Their Couples Retreat Package ($226) is an overnight stay, complete with two glasses of champagne, two heart-shaped brownies (the hotel is where the treat was invented), and 30% off all spa services. 

In Lakeview, the Fred Astaire Dance Studio has a pair of classes. Feb. 12^th is Sip & Dance ($50/person), which takes place at Bottles Up. You’ll learn to waltz, tango, and rumba with a wine pairing selected for each dance. At Astaire’s studio the next day, Tango & Chocolate ($75/couple) combines those two, and adds champagne. 

From Feb. 12^th-14^th. Coquette’s prix fixe dinner ($60/person) consists of four courses of French cuisine. Plates at the West Loop bistro include bouillabaisse, red-wine braised short rib, citrus-cured salmon, foie gras, escargot, and roasted butternut squash. 

The Chicago Candle Co. in Pilsen lets you take an old wine bottle (either bring your own or choose from their selection) and convert it into a soy candle. For $60/person, you’ll learn how to cut the bottle—safely!—into the proper shape and pour the wax, which comes in cocktail scents like Barrel-Aged Bourbon, Irish Coffee Stout, or Pumpkin Buttered Rum. Feb. 14^th is sold out, but there are limited spaces on Feb. 13^th and 15^th.

Lastly, in addition to all the other attractions at Navy Pier that can make for a memorable Valentine’s Day, they’ll have their famous fireworks show starting at 9 PM.