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15 Romantic Ways To Spend Valentine’s Day In Chicago

Secret Chicago Secret Chicago

15 Romantic Ways To Spend Valentine’s Day In Chicago

Show them how much you care with an experience they won’t forget.

Valentine’s Day is quickly approaching which means it’s time to start planning the perfect night of romance. If the love between you and your other half has only flourished during one of the most restrained, anxiety-inducing years in recent history, congratulations. Of the nearly 8 billion people currently orbiting the sun, it sounds like you’ve found a keeper and that is reason to celebrate.

If there’s a new flame in your life then congratulations all the same, here’s to the future!

Chicago is full to the brim with heart-fluttering activities and there are many ways to celebrate your relationship this year despite restrictions and closures. Here are some of the most romantic ways to celebrate Valentine’s Day in Chicago.

1. Marvel At The Magic Of A Candlelit Concert

There are few things that pull at the heartstrings with more power than live music in its purest form. Add to that the tender flicker of one hundred candles and the charm of Salvage One’s reclaimed vintage venue and you have an unrivaled recipe for romance. The spellbinding Candlelight concert series returns to Chicago this February for five Candlelight: Romantic Valentine specials and they present the perfect night of romance.

Enjoy some of history’s greatest love songs played out masterfully in front of your eyes as the gentle flicker of flames dance around you and the strings soothe and swoon you. Worry not, the candles are fireproof, so the only sparks flying will be the metaphorical sparks between you and that special someone. These romantic concerts might not fall on actual Valentine’s Day, but they make the perfect gift.

2. Discover The Love Stories of Chicago

Image from Shuttershock

If you’re keen to go out and about despite the weather and your love for Chicago is bettered only by your love for your other half this might be the perfect date for you.

On this exclusive tour, you will visit the most romantic places in the city together with a professional local guide who will tell you about love stories hidden in the streets, buildings, and parks of the city whilst explaining the best places for dates and where to take the most romantic photos.

You will be surprised how many historical anecdotes exist within the makeup of the Windy City. From heartbreaking and tragic tales to hilarious and spicy sagas. The Guided Tour “Love Stories of Chicago” is a surefire way to have the romance resonating between you and your partner.

3. Cool Off At AIRE’s Ancient Baths

Image from Beaire.com

There is simply no better place in Chicago for some rest and relaxation than AIRE’s Ancient Baths and this Valentine’s day they are offering exclusive Endless Love Experiences For Two.

Located in a restored historic River West factory dating back to 1902, the baths are inspired by the traditional Roman, Greek, and Ottoman ancient experience of bathing. This preserved structure has been restored to its original splendor and you can now find optimum relaxation within the exposed brick, wooden beams, and industrial columns of the building.

The unique body and mind experience offers baths of different temperatures, relaxing massages, and couples experiences. It’s almost impossible for anything to go wrong at a place where all stress and pressure evaporates into thin air!

4. Fall In Love Surrounded By Fish

Image from Pexels

On the topic of aqua-related activities, Shedd aquarium has only just reopened and with a lack of tourists, it is a brilliant chance to enjoy the extraordinary exhibits without the usual crowds. There is something so soothing about aquariums and they have actually been proven to reduce stress and anxiety. Watching fish can lower blood pressure similar to meditation and consequently makes for a relaxed, no-fuss date.

Youn can also treat your other half to some romantic virtual encounters like the sea lion kiss, or a number of other Valentine’s Day gifts perfect for aquatic animal lovers.

5. Create A Masterpiece Together

Image from Shuttershock

Treat your date to a fun and stress-free painting party with this 1.5-hour virtual course and create something that’ll either impress or entertain your other half.

In this Paint with a Partner virtual experience an expert artist from Italy will guide you through the creation of a fun and creative painting. As a couple, together you will create one painting made of two canvases: each partner will paint on an individual canvas that will be the matching half to their partner’s painting.

You can use your own tools if you have them; otherwise, just order a paint kit and everything you need will be delivered straight to your home. It’s the perfect way to release your inner creativity on Valentine’s Day and you’ll create a material memory in the process.

6. Go Classic With Dinner & A Movie

Image from Unsplash

The age-old recipe for romance just doesn’t fail. A meal and movie night is always a winner and with cinemas reopening this February, there has never been a better time to go to the movies. Book tickets to a showing, watch that screen light up filling you both with excitement and snuggle up for a cinematic experience like days of old.

At AMC Theatres you can dine on delicious meals while watching the newest flicks. Secret Chicago readers can get tickets to the best theater experiences for an exclusive price by downloading the Fever app.

7. Enjoy A Personalized Poetry Show

If you aren’t too keen on heading out to the movies just yet this Live Love Odyssey Show might be the thing for you.

The Poetry Society has tried traveling back to the roaring 1920’s for Valentine’s Day. The Madame set the dial on the time machine to 1921, the year D.H. Lawrence released Women in Love, and Fitzgerald published The Beautiful and Damned. “What a romantic time…” we all thought to ourselves, “we are certain to find love!” Unfortunately, SOMEBODY poured whiskey in the time machine, sending us FORWARD 100 years instead of back!

Come and be transformed by this uniquely personalized Valentines Day Love Odyssey Live Show, featuring Puss N Boots, Velvet Envy, Tennessee Pink, Too Loose, the Madame, and many more!

8. Go Ice Skating In Maggie Daley Park

Image from Instagram / @maggie.daley.park

Ice-skating in Maggie Daley Park is one of Chicago’s most beloved winter-time activities but it can also offer a guaranteed night of romance for long-term couples and blossoming romances in equal measure. There is something extra special about gliding around the quarter-mile winding ribbon of ice with the city skyline in the backdrop and the stars above. Whether you’re showing off your skills or hysterically struggling to stay on your feet, you can be sure you and your special someone will be having fun.

9. Revel In A West Loop Winter Wonderland

Recess in Chicago’s West Loop is home to a 14,500-square-foot space that holds the title of Chicago’s largest patio and you can bet your bottom dollar there is always something fun happening down there. This February they have revamped their notorious patio and are hosting a cocktail-concocting candyland pop-up by the name of Sugar Rush.

Nestled within 30 shipping containers on a West Loop corner, Recess and its cozy amalgamation of bars, food stands, and cabana houses offer and an awe-inspiring setting whilst firepit tables and boozy hot chocolates present the perfect recipe for a unique and intimate Valentine’s evening.

Every ticket to Recess’s The Sugar Rush Pop-Up comes with a Sugar Rush specialty cocktail, a boozy Recess Peanut Butter Hot Chocolate, a Gourmet Rice Krispie treat, a Recess beanie hat, and a goodie bag of extra sweet treats. So you can rest assured you’ll stay toasty warm while getting a little bit tipsy in this snug sanctuary.

10. Head To The Rooftops

Of all the social spots and watering holes across Chicago, it’s up among the rooftops where the most romantic nights can be had. Though indoor dining is seeing a slow return, there are many winter wonderland setups up still going strong among the Chicago skyline.

A standout option is the Heated Winter Wonderland Rooftop And Holiday Cocktails at Joy District. Sparkling lights, comfortable patterned couches, and impeccable views of Chicago’s skyline guarantee a memorable night but the magic of vibrant murals and cascading greenery make Joy District’s rooftop a truly unique space.

Both Rooftop Ski Lodge and Rooftop Winter Igloos can also now be rented ensuring a safe and private space to drink beneath the Chicago stars and skyscrapers but you’ll have to be quick because tickets are going fast.

11. Take A Culinary Journey At West Loop’s Rooh

Image from Shuttershock

Another extraordinary outdoor experience can be had at Rooh in West Loop. The Indian restaurant prides itself on its progressive Indian cuisine offers an array of exquisite moderately-priced dishes merging exquisite regional flavors and modern gastronomic techniques.

The real magnum opus is a 4-course prix fixe Indian Culinary Journey that invites guests to experience local flavors and traditions from various regions of India. With a 17-foot heated hexadome tent you and your other half can snuggle up and take a trip to the far east to enjoy another culture and lifestyle while international travel is off the cards.

12. Share A Heart-Shaped Pizza

Image from Shuttershock

If you’re at that stage where you can happily tuck into some fast food without a care in the world these famous heart-shaped, deep dish pizzas are the perfect way to literally eat your heart out. You can find delicious heart-shaped pizzas at Lou Malnati’s, Giordano’s, My Pi Pizza, Eataly, and many other pizza restaurants in Chicago. Celebrate Valentine’s Day the Chicago way by slicing into cheesy heaven.

13. Hunt Down Chicago’s New Art Installations

Image from Unsplash

If there’s one thing to rival Chicago’s food scene it’s our eminent art scene. Acclaimed museums contain some of the most famous works of art on the planet whilst Chicago itself is full of art by sculptures, artists, and architects of worldwide fame. Whether you’ve been active throughout lockdown or found yourself confined to the couch a romantic stroll with your partner is great not only for mental health purposes but also to catch up away from your phones, laptops, and other screens.

A walk to the various different art installations in our great city makes for a wonderful Valentine’s Day plan that will have you both fervently sharing your thoughts and ideas.

You’re likely already familiar with works like Calder’s Flamingo and the Picasso Statue but you and your special somebody might not yet have heard of some of the new additions. Santiago Calatrava’s ‘The Constellation’, went up in Chicago in November whilst Olafur Eliasson’s ‘Atmospheric wave wall’ was installed at the start of 2021. Both provide breathtaking pieces of art that are well worth hunting down.

14. Peruse The Many Magnificent Murals Of Chicago

It might be that you and your other half are more interested in street art than sculptures and if so a scavenger hunt of Chicago’s best murals is another wonderful Valentine’s activity. Again, this is an activity that will have you lost for words but never lost for conversation.

The caliber of street art in Chicago is constantly astounding and the latest masterpieces to have gone up in Chicago over the past year are even more poignant than ever before. Murals we saw in 2020 fight for racial equality, celebrate different heritages, and honor the essential workers of our societies. They’ve now embedded themselves in the fabric of our city and offer an insightful, intimate, and interesting experience. Wrap up warm, research some of the backstories of the most famous murals, and take your pick from Chicago’s 20 Must-See Street Art Murals.

15. Enjor An Entertainment-Mixology Experience

We completely understand if heading outside isn’t appealing to you at the moment and one activity that will certainly make for a memorable Valentine’s Weekend is the Speakeasy Cocktails and Burlesque Experience.

This new entertainment-mixology experience delivers ten finely crafted cocktails to your door so you can sip away while watching electrifying performances. Decadence is delivered to your door so you can enter a world where tipsy temptation awaits. Featuring some of the top cirque, burlesque, illusion and theatrical performers in the world Speakeasy on Demand brings a naughty rendezvous to you and lets you and your partners imagination run wild.

Looking for more date ideas? Browse Valentine’s Day plans here.

[Featured image from Pexels]