Chicago is the perfect place to spend Valentine’s Day. The city offers the ideal mix of big-city romance and cozy winter vibes, whether you’re looking for a laid-back activity (like a cooking class for two) or an over-the-top adventure (perhaps a luxe dinner cruise along the river).

Start planning your only-in-Chicago Valentine’s Day and treat your sweetheart ― or yourself! ― to something special this year. And with Valentine’s Day falling on a Saturday, you have the perfect excuse to turn your date night into a full-blown romantic weekend.

Here are some of our favorite ideas for things to do for Valentine’s Day 2026 in Chicago.

Romantic ideas for Valentine’s Day in Chicago

Whether you’re looking for a low-key night out or an over-the-top celebration, Chicago has plenty of ways to lean into the romance this Valentine’s Day. Here are some of the best ways to feel the love in Chicago:

  • Romantic restaurants: Grab a table at a swanky Michelin-starred spot, a tiny French bistro, or an upscale steakhouse for a classic candlelit dinner.
  • Unique events: Catch a waterfront fireworks show, discounted theatre tickets, a floral showcase, and so much more.
  • Fancy hotels: Reserve a room for the weekend with special holiday packages offering perks like complimentary champagne and late check-out.
  • Unforgettable experiences: Make a grand gesture by booking a helicopter tour for two, a relaxing spa day, or a stunning dinner cruise along the lakefront skyline.

Valentine’s Day restaurants

It’s not Valentine’s Day without a romantic candlelit dinner. Enjoy a night out with your sweetheart at these top Chicago restaurants for Valentine’s Day, ranging from Michelin-star winners to homey neighborhood favorites.

  • Feld: Impress your date with reservations at Feld, Chicago’s newest Michelin-starred restaurant.
  • Le Bouchon: This tiny bistro in Bucktown serves authentic French cuisine with the perfect cozy vibes.
  • Chemistry: The cuisine, cocktails, and presentation are all top-tier at this Hyde Park steakhouse.
  • Adalina: In the swanky Gold Coast area, Adalina offers a refined atmosphere and upscale Italian cuisine.
  • La Grande Boucherie: Transport your sweetheart to Paris at this stunning downtown brasserie, known for its jaw-dropping interior.

  • Esmé: Indulge in an artistic tasting menu at this award-winning Lincoln Park spot.

Explore more: Check out our guide to top spots for a romantic Valentine’s Day dinner in Chicago.

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Romantic hotels in Chicago

Kimpton Gray

Valentine’s Day falls on a Saturday in 2026, which is the perfect excuse for a long weekend getaway. Check out these Chicago hotels offering special Valentine’s Day packages, featuring complimentary champagne, chocolates, and more — the perfect way to surprise the one you love.

  • Sophy Hotel Hyde Park: The SO-Suite experience features a suite inspired by the neighborhood’s rich history, along with complimentary parking and a credit for the elegant in-house restaurant.
  • The Gwen: The Skyline Sweethearts package includes a bottle of bubbles, rose petal turndown service, late check-out, and more.
  • The Drake: This historic lakefront hotel is offering A Toast to Love, which includes handcrafted martinis at the opulent Coq d’Or bar.
  • LondonHouse Chicago: Enjoy a relaxing weekend with the Spa Stay package, featuring a credit toward your choice of indulgent spa services.
  • Nobu Hotel: Take advantage of discounted room prices this winter and enjoy elegantly appointed rooms and the sweeping views at the rooftop bar.

  • Palmer House: Celebrate your love with the Couples Retreat Package, featuring complimentary champagne, heart-shaped brownies, and access to the indoor pool and stunning lobby bar.

Explore more hotel options in Chicago for your Valentine’s Day retreat.

Unique Valentine’s Day activities

City Experiences dinner cruise on the Chicago River

Make it a Valentine’s Day to remember with an only-in-Chicago activity or event. Set sail on a scenic dinner cruise, grab tickets to a live performance, or admire the view from one of the world’s highest observation decks.

Events and happenings

@choosechicagoFeel the love on Valentine’s Day with a free special themed fireworks display at Navy Pier! ❤️🎆 📍 Navy Pier 📅 Friday, 2/14 at 9pm Launching from Lake Stage in Polk Bros Park♬ original sound – Choose Chicago

Unique activities

  • Winemaking Dinner: This hands-on winemaking experience includes dinner, a wine and mead tasting, and the opportunity to create your own custom blend to bring home.
  • City Cruises Chicago: Set sail on a breathtaking dinner cruise, featuring live music, plated dinner, and stunning panoramic views of the city at night.
  • Get a Grip Trapeze: Get your heart pumping and learn the thrilling art of flying trapeze at these indoor classes for beginners.

Skyline views

  • Fly Heli Chicago: Make it an unforgettable evening with a Valentine’s Day helicopter tour of Chicago. Choose from private and group flights.
  • 360 CHICAGO: Hover more than 1,030 feet in the air during the TILT ride at 360 CHICAGO. Calm your post-TILT nerves with a drink at CloudBar, with soaring lakefront vistas.
  • Skydeck Chicago: Another great activity for adventurous couples: an elevator will whisk you 103 floors up the iconic Willis Tower, where you can dare to stand on The Ledge, a glass floor balcony with breathtaking city views.

Outdoor adventures

  • Skating Ribbon at Maggie Daley Park: Snag a reservation, rent skates (or BYO), and take a spin around this scenic ice rink with unbeatable views of the park and downtown.
  • Rooftop curling at The Gwen: Try your hand at iceless curling on the rooftop terrace of the Gwen Hotel, with fire pits and warm seasonal cocktails.

Speakeasies and cocktail bars

Inside Three Dots and a Dash
Three Dots and a Dash
  • The Drifter: Catch tantalizing burlesque performances and delicious craft cocktails at this intimate underground speakeasy.
  • Nobody’s Darling: This acclaimed LGBTQ+ friendly lounge has an outstanding cocktail and mocktail program.
  • Three Dots and a Dash: Find the hidden alleyway entrance and descend into a tropical speakeasy, known for over-the-top tropical cocktails.
  • Meadowlark: This cocktail bar inspired by vintage Chicago features a warm, dimly lit space with a curated menu of bar snacks and creative cocktails.
  • Cantina Rosa: This new cocktail bar in Hyde Park offers a sophisticated ambiance and a drink menu inspired by Mexican heritage.
  • The Aviary: From the team behind globally acclaimed Alinea, The Aviary offers a tasting menu of customized avant-garde cocktails.
  • Nine Bar: Tucked away behind a beloved Chinatown restaurant, this buzzy speakeasy serves modern takes on classic drinks and dishes.

Explore more: Find more ways to get cozy in Chicago this winter for Valentine’s Day and beyond.

Spas, saunas, and beyond

AIRE Ancient Baths

Spend your weekend indulging in some self-care or a wellness retreat for two. Get toasty in a waterfront sauna, gently float in candlelit baths, or splurge on a relaxing couples massage

  • AIRE Ancient Baths: Submerge yourself in relaxation at this spectacular bath house, housed in a restored 1900s factory. Enjoy saltwater baths, scented steam rooms, and specialty massages.
  • Kiln Floating Sauna: This unique Nordic-inspired experience allows you to both sauna and cold plunge with breathtaking skyline views.
  • Chuan Spa at The Langham: Treat yourself and your date to a day pass at this luxe hotel spa, featuring aromatherapy showers, heated loungers, a lap pool, and more.
  • Piva Beer Spa: This unique hops-focused spa includes steam rooms, saunas, and beer soaks for solo spa-goers and couples.
  • The Peninsula Spa: The luxury spa at this five-star hotel on The Magnificent Mile offers an array of relaxing private treatments like aromatherapy massage, full-body scrubs, and more.
  • The Four Seasons Hotel Chicago Spa: Choose from top-of-the-line facials and body treatments, or opt for the exclusive night spa experience that’s perfect for couples.

Explore more: Make it a self care Valentine’s Day weekend with more spas and wellness activities.

Rooftop bars with a view

IO Godfrey

What’s more romantic than a glass of champagne with stunning skyline views? These all-season rooftops are decked out for winter, making them the perfect spot for a special-occasion date night.

  • I|O Godfrey: The year-round rooftop bar atop The Godfrey Hotel has launched its ultra-festive winter space featuring its popular heated igloos.
  • The Kennedy: Cozy up by a fire pit while soaking in the panoramic views of the city skyline. Or order bottle service from your private covered igloo.
  • VU Rooftop Bar: This unique South Loop space boasts a one-of-a-kind perspective of the city skyline.
  • Offshore: The largest rooftop bar in the world offers stunning views of the surrounding water and cityscape.

Explore more: Find the best winter rooftop bars all around Chicago.

Shows, concerts, and burlesque

Chicago’s stages are offering a bit of everything for your Valentine’s Day date, whether you love comedy, drag, burlesque, or beyond. See what’s playing for Valentine’s Day weekend (and check Chicago Theatre Week to score discounted tickets from Feb. 5 – 15).

  • The Second City: Make a date with this iconic comedy club, where hilarious sketches and improv always make for a laugh-filled evening.
  • The Magic Parlour: This jaw-dropping show, featuring third-generation magician Dennis Watkins, will make a spellbinding date night.
  • Broadway in Chicago: Catch the latest Broadway hits and exciting premieres at Chicago’s historic downtown theatres. On Valentine’s weekend, The Outsiders will be playing at the Cadillac Palace Theatre.
  • Bordel: This moody Wicker Park speakeasy features live entertainment all weekend long, from flamenco to burlesque.

Explore more: Check out more events and shows with our events calendar.