Valentine’s Day Date Ideas for Chicagoland Couples

Try these 10 creative ideas for spending some romantic couple time around Chicago.

Sure, you love your significant other, but do you sometimes run out of things to talk about besides kids and schedules? Getting out of your typical routine does wonders for rekindling the romance of the pre-children days. Try these unusual and exciting activities together to re-spark the fun and remind yourselves why you got together in the first place. 

Spin some art

Watch the colors fly when you visit Spin Art Nation, a trendy new paint studio in Lincoln Park. Work together to create unique art by splattering paint on spinning canvases. Laughs and lasting memories are sure to be made. Plus, everyone looks especially cute dressed in protective suits and boots.

Add a dash of magic

Dress in your best cocktail attire and head to The Magic Parlor at the Palmer House Hotel for a magic show that will cast a spell on you. Third-generation magician Dennis Watkins reads minds, performs sleight of hand and baffles audiences with other impressive illusions in a private ballroom. Complimentary beer, wine and soda are served before the show. 

Staycation in the suburbs

Escape to the same estate that legendary crooner Frank Sinatra would retreat to after shows in Chicago, the Drake Oak Brook. Down the street from the Oakbrook Center, you’ll find this upscale hotel perfect for getting away from the hustle and bustle. 

Indulge in the Be My Valentine Brunch on Feb. 12, or Cupid’s Celebration Valentine’s Dinner or a private igloo dinner on Feb. 14. But, the best part is the Love at the Drake package, which includes a rose-filled suite, personalized Bellinis, chocolate covered strawberries, a couple’s massage, private limo experience through downtown Chicago, breakfast in bed and late checkout. Talk about the ultimate overnight!

Surround yourselves with wine

If you’re a couple of wine lovers, then take your wine outing up a few notches by visiting the new Chicago Winery, which opened in late 2022. It’s a gorgeous, contemporary setting for a wine tasting or tour. Partake in their Valentine’s dinner or head to Alpana, a chic bistro serving wine-inspired cuisine. Alpana’s staff is super knowledgeable about exquisite food and wine pairings. The braised short ribs and mushroom ravioli on their Valentine’s Day menu are to-die-for. Then, top it all off with a soak in red wine at AIRE Ancient Baths. Yes, submerge yourselves in a private bath of Spanish Ribera del Duero red wine and see where the rest of the night takes you!

Drink in views of the Windy City

Toast to your love for each other from CloudBar on the 94th floor of 360 CHICAGO, the former John Hancock building. Get hearts racing on TILT, the attraction that angles visitors over Michigan Avenue. Then, clink glasses while you take in gorgeous skyline views at CloudBar, where you can delight in drinks like the Heavenly Martini, which is topped with a puff of cloud. Beer aficionados will appreciate the Magnicity Pilsner brewed by the world’s first two Michelin star brewery, Moody Tongue. And if your Dry January is continuing through February, then Here Comes the Sunset is for you. Inspired by the Gold Coast neighborhood, this alcohol-free libation is just the perfect way to cap off your romantic night. 

Have a ball interacting with art and color

Opened in spring of 2022, Color Factory is an immersive art museum located on the bottom floor of Willis Tower. Pops of bright colors, playful sights, interesting sounds and sweet treats create a dazzlingly different date night. Draw your partner’s features and share sweet nothings across opposite sides of glass, jump in the ball pit, and feel a bit of nostalgia while eating Pop Rocks. Color Factory might be just the experience you need to feel head over heels again. 

 Trick Your senses with illusions

Museum of Illusions Chicago is one of almost 40 illusions museums globally. Located steps from Millennium Park, this small, engaging museum features exhibits that will have you saying “wow!” and “how?” Some illusions even make you the star of the show. Get your cameras ready because it’s sure to be a selfie-filled expedition. 

Dine on charcuterie

Libertyville is an adorable northern suburb with a new, swanky charcuterie restaurant, The Board Room. Opened in December with a high-end interior and cozy solarium, The Board Room is the perfect place for you and your sweetheart to canoodle over craft cocktails, curated charcuterie and delectable small plates. There are 3 seasonal charcuterie boxes to choose from, and the Moroccan Heirloom Carrot Salad is probably one of the most delicious salads ever made. From 8-11pm on February 11, The Voice contestant and Illinois native, Lauren Hall, will be there melting hearts. Work up your appetites by creating your own DIY wood sign project at the Board & Brush down the street beforehand. 

Sample a symphony of flavors and sounds 

The music and setting of a Chicago Symphony Orchestra concert are simply stunning. In December, Forte, a contemporary Mediterranean restaurant opened in the Symphony Center, serving delicious dishes to delight taste buds before or after shows, or even on days in-between. Dip warm, savory rosemary focaccia in whipped feta, then share bites of Ahi tuna in red curry cream sauce. Celebrate your love with cinnamon and clove muddled wine or spirit-free cocktails that aren’t missing an ounce of pizzazz. 

See a swoon-worthy show

Chicago Theatre Week, February 16 – 26, is a great way to snag tickets to shows like The Blue Man Group, Broadway in Chicago and Broadway in Bronzeville for as low as $15 or $30. If you’re looking for sultry performances on Valentine’s Day, check out sexy cabaret dinner show “LUMINAIRE” or laugh out loud at “Men Are From Mars, Women Are From Venus LIVE!”, a one-man standup comedy show with relatable bits about dating and marriage.


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Cortney Fries
Cortney Fries
An award-winning travel journalist, Cortney Fries (pronounced "freeze") has been writing about family travel for over a decade. She knows that parents planning trips are looking for all members to have fun and make lasting memories. Cortney believes that you should definitely try anything that makes you slightly nervous.
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