Valentine's day events in Chicago in December

Valentine’s Day 2026 Celebrations In Chicago

Chicago will certainly host a memorable Valentine's Day celebration in 2026! The city is brimming with romantic activities and festivities this year for friends, couples, and families. There is something to enjoy for everyone, including special discount offers, live music events, and romantic dinners. Chicago has everything you need for a great night out with friends or a romantic evening out with your special someone. You may find something to fit your interests thanks to the city's thriving nightlife, bustling shopping areas, and availability of good eating. So on this Valentine's Day, don't pass up the chance to celebrate love in the Windy City!

Things To Do On Valentine’s Day 2026 In Chicago

Celebrate Valentine's Day 2026 in Chicago with enchanting experiences for couples. Enjoy a leisurely lakeside stroll, indulge in a gourmet brunch, and pamper yourselves with a spa day. As the sun sets, savor a romantic dinner cruise along the Chicago River amidst dazzling city lights. For cultural enthusiasts, explore art museums or attend a live performance. Chicago's vibrant energy makes Valentine's Day a memorable and romantic occasion for couples to cherish.

1) 2026 Chicago Winter Tequila Tasting Festival 

The 2026 Chicago Winter Tequila Tasting Festival takes over King’s on February 14th for an exclusive Valentine’s Day celebration of agave spirits. Featuring a curated selection of over 20 premium tequilas and mezcals, the event allows guests to sample craft expressions and learn from brand ambassadors in a high-energy setting with live DJ music. VIP attendees enjoy elite perks including early entry, a food buffet, and exclusive access to top-shelf bottles valued at $80 or more. With a strict 299-person capacity and proceeds from extra tasting cups benefiting the Bear Necessities Pediatric Cancer Foundation, it offers an intimate, philanthropic, and flavor-packed experience for connoisseurs and newcomers alike.

2) Tipsy Cupid Sip & Sail Valentine's Day Yacht Cruise

Make this Valentine’s Day a double-header with two premier Chicago events. Start your afternoon at King’s in Lincoln Park for the 2026 Winter Tequila Tasting Festival, where you can sample over 20 premium spirits and enjoy VIP perks like top-shelf pours and a buffet. Once the tasting wraps up, head over to Burnham Harbor to board the Tipsy Cupid Sip & Sail Yacht Cruise. This three-level party on the Anita Dee II features heated indoor dance floors, a romantic skyline backdrop, and live sets from Power 92’s DJ Nehpets. Whether you’re bonding over agave treasures or dancing under the stars, these back-to-back experiences offer the ultimate spirited celebration of love and city vibes.

3) Cupid’s Castaway Karaoke

Turn Valentine’s Day into an epic Chicago marathon with four distinct celebrations. Kick off the festivities at King’s in Lincoln Park for the Winter Tequila Tasting Festival, featuring over 20 premium agave spirits and VIP perks. As the afternoon winds down, head to Trader Todd’s in Lakeview for Cupid’s Castaway Karaoke, where you can sip tropical rum drinks and belt out love songs in a tiki-lit paradise starting at 5:00 PM. From there, take a short trip to Theater on the Lake for the 3rd Annual All 80's Prom to dance to live hits by Tributosaurus and snap retro prom photos. Finally, cap off the night at Burnham Harbor by boarding the Tipsy Cupid Sip & Sail Yacht Cruise at 10:30 PM, where three levels of music and sweeping skyline views provide the ultimate romantic finale on Lake Michigan.

4) 3rd Annual All 80's Prom

Make this Valentine’s Day a high-energy "triple threat" across Chicago. Start your afternoon at King’s in Lincoln Park for the 2026 Winter Tequila Tasting Festival, featuring over 20 craft spirits and VIP top-shelf pours. As the sun sets, head just a few minutes east to Theater on the Lake for the 3rd Annual All 80's Prom, where the band Tributosaurus will be rocking decade-defining hits and a professional photographer will capture your retro prom glory. Finally, keep the romance and rhythm alive by heading south to Burnham Harbor to board the Tipsy Cupid Sip & Sail Yacht Cruise. With three levels of music, heated dance floors, and breathtaking views of the Chicago skyline, this midnight sail on the Anita Dee II is the perfect finale to an unforgettable holiday in the city.

5) RATIO: Rosé Lounge

While the RATIO: Rosé Lounge serves as a stylish "Month of Love" wrap-up on February 21st, Valentine’s Day (February 14th) in Chicago offers a packed four-event marathon. Start with the Winter Tequila Tasting Festival at King’s for premium agave flights, then head to Trader Todd’s for tropical Cupid’s Castaway Karaoke. Keep the energy high at the 3rd Annual All 80's Prom at Theater on the Lake for live music and retro photos, before finishing the night aboard the Tipsy Cupid Sip & Sail Yacht Cruise for a moonlight party on Lake Michigan. One week later, you can keep the vibe alive at Bodega Taqueria y Tequila for the intimate RATIO: Rosé Lounge speakeasy party.

Best Places To Go On Valentine's Day In Chicago

Sprinkles of love spread in the air on Valentine’s Day in Chicago. It is when all the cheeks blush with beautiful celebrations around the city. Take your loved one to gorgeous parties, cruises, workshops, restaurants, or a cozy movie night; the choice is yours!
Chicago has some fantastic venues that hosted Valentine's Day events & parties last year; find them below:

• 2136 W Chicago Ave
• Lakefront Trails
• 3414 W Foster Ave
• 11946 S Halsted St
• Duet Dance Studio
• The Promontory
• Get in the Kitchen
• Ballroom Dance Chicago West Loop
• Ballroom College
• Vault Gallerie
• Ballroom Dance Chicago Lakeview
• Davenport's Piano Bar and Cabaret
• The Newport Theater
• Miki's Park
• Fleet Feet Old Town

Where Should I Go On Valentine's Day In Chicago

As February approaches, everyone looks for the perfect way to celebrate Valentine’s Day in Chicago. Don’t break your sweat because the city has the ideal romantic ways to celebrate love with your beloved at the best restaurants, events, and attractions in the Chicago.
Here is a list of some marvelous venues in Chicago for the best Valentine’s Day events and parties of last year:

• The Shops: Valentines Day Edition - VEND / ATTEND was hosted at Water Tower Place.
• Crazy in Love:Y2K Valentines Day Candle Making workshop was hosted at 2711 W 51st St.
• Valentines Day Pop Up Event was hosted at 5709 W Irving Park Rd.
• LOVERS & FRIENDS: The Pre Valentines Day + Super Bowl Weekend Kickoff Party was hosted at Flash Dance Club.
• Teenage Bottlerocket Valentines Day Special with Raging Nathans and Won't Stay Dead at Reggies was hosted at Reggies.
• Valentines Day Party was hosted at 4339 W 18th Pl.
• Valentines Day Show With The Kantors, Friday James, and Michelle McCarthy was hosted at Golden Dagger.
• Valentines Day Mixer was hosted at Private Venue.
• Dee Alexander Quartet - Valentines Day at the Jazz Showcase was hosted at Jazz Showcase.
• A Lovely Night above the Lights Valentine's Day Dinner and Aquarian Gala was hosted at Willis Tower.
• VALENTINE'S DAY CELEBRATION AT ALHAMBRA PALACE CHICAGO was hosted at 1240 W Randolph Street.
• A Bougie Elegance Valentine’s Day Popup was hosted at Bethany Union Church of Chicago.
• Ian Maksin at Artifact Events in Chicago. VALENTINE'S DAY CONCERT was hosted at Artifact Events.
• Noche De Risas Comedy Show @ Headquarters Chicago - Valentines Day Edition was hosted at Headquarters Chicago.
• Fleet Feet Old Town Pre- Valentine's Day Demo Run with ASICS was hosted at Fleet Feet Old Town.