JAN 2023

Destinations in the Windy City that’ll make your Valentine go “Awww”.

Looking for the best things to do on Valentine’s Day in Chicago?

Wondering how to sweep your Valentine off their feet this year?

Searching for the best events and activities to take your special someone to, on perhaps the most important Tuesday this February?

We got you!

Celebrating Valentine’s Day 2023 in Chicago

With its rich culture, great food, and diverse entertainment options, The Windy City is a great place to celebrate the patron saint of love - St. Valentine.

Whether you're looking for a thrilling adventure (such as an escape room?), a relaxing activity (like a spa day), or even an offbeat experience (like a spot of urban exploration)...

We've got some great options for you to celebrate Valentine's Day with your significant other in Chicago.

Attend a candlelight concert at Cafe Brauer


The image is taken from their global website (

Want a quintessentially romantic experience for Valentine's Day in Chicago?

Attend a candlelight concert!

Part of a global event, Candlelight Concerts in Chicago is a series of unique musical events that take place amidst hundreds of flickering candles.

On Valentine's Day, they have a performance scheduled at the historic Café Brauer.

From all-time classics like Tchaikovsky's Rome & Juliet to modern favorites like Guns N’ Roses' Sweet Child O’ Mine and the theme from 1970's Love Story - the program draws from various genres of music.

A truly moving tribute to the sacrifice of Saint Valentine.

Date & Time: Tuesday, February 14th, at 6:30 PM and 8:45 PM (two 65-minute long sessions)

Website: Visit their Chicago website

Location: Check address/Plan route (for Café Brauer, the location) on Google Maps

Team up for an escape room adventure at Fox in a Box


Discussing their next move…

Looking for a thrilling Valentine’s Day adventure in Chicago that’ll have your special someone saying “WOW!”?

Head for the Dearborn Station, where you'll find Chicago's premier escape room - us.

As you enter our facility, you and your significant other will be briefed on your mission.

Next, you'll be led into a specially set-up room where the adventure takes place.

As the clock starts ticking, look for clues on how to proceed. Work as a team to solve puzzles, break codes, find secret panels, and open special locks to find clues.

Can you get to the final clue and accomplish your mission before you're out of time?

You have four exciting escape room missions, based on diverse themes, to choose from.

Ready to test who's the bigger Sherlock this February 14th?

Nearby places for a post-experience dinner

Website: Visit the home page

Location: Check address/Plan route on Google Maps


Phone: (312) 878-7899

Go skating


Suit up, and go for a glide on the ice!

Ready for a Valentine’s Day activity that’ll prove a good workout while giving you two plenty of opportunities to have memorable moments outdoors?

Head to a rink, suit up, and go ice skating!

Breathe in the crisp February air as you try to conquer the course.

Watch for the twists and turns, and keep up with your partner.

Whether you’re barely managing to stay up straight, or you’re gracefully gliding across the rink, skating can be an awesome activity to share with your Valentine in Chicago!

Tip: Most venues offer skate rentals, so there’s no need to carry your own.

Where to go ice skating on Valentine’s Day in Chicago

Enjoy a romantic dinner


Will you actually hold hands?

Want to make February 14th in Chicago an occasion you’ll really…relish? Enjoy a romantic dinner with your partner!

And you certainly have a lot of options to choose from!

Sitting in Chicago, we HAVE to mention enjoying deep-dish pizzas at one of the numerous pizza joints dotting the city.

If you're looking for a more upscale culinary experience, head for one of the renowned steakhouses.

Prefer to have a spectacular city view as the backdrop? Several rooftop restaurants fit the bill.

Whatever your desired cuisine - American, Continental, Mediterranean, or Asian - and other preferences, you're sure to find a Chicago restaurant that's right for you!

A few Chicago restaurants that you can look at for Valentine’s Day dinner

  • Lou Malnati's on State has a tradition of offering special heart-shaped pizzas to mark the day.

  • Geja’s Cafe is famous for its food-wine pairings…need we say more?

  • Boka will be offering a ‘specially crafted 7-course tasting menu’ on the occasion.

  • Cité offers spectacular views of the lakefront in addition to exquisite French-inspired dishes.

  • And finally, Komo (known for its Japanese cuisine) has a 'decadent 4 course menu' lined up for the day.

Dine in the dark

Looking for a unique twist on the classic romantic dinner? Try this on for size - dining in the dark!

And no, we're not kidding!

This is a singular Chicago event where you're blindfolded before being served a full three-course meal (paired with wine)!

They don't even reveal the menu in advance. While you can make a basic choice amongst vegan food, seafood dishes, and meat-based cuisine, the rest is kept under wraps till you take the first bite.

Ready to experience culinary mastery as you've never experienced before?

Website: Visit the website

Location: Check address/Plan route (for Hubbard Inn, the location) on Google Maps

Take in breathtaking views of the city


Gazing at the Chicago skyline with your significant other, especially at nighttime, is a perfect way to take in the beauty of our city while enjoying time as a couple.

The sheer diversity of architecture spread out all over Chicago, lit up by thousands upon thousands of sparkling lights, are sure to prove the perfect backdrop for an intimate, romantic moment.

The best ways to behold Chicago’s skyline with your Valentine

  • Skydeck in the Sears (a.k.a. Willis) Tower offers sweeping views of the city and beyond from inside clear glass observation boxes.

  • 360 Chicago in the former John Hancock Tower affords you dazzling views of the city looming over the gleaming waters of Lake Michigan.

  • The Centennial Wheel at the Navy Pier is another way to take in the Chicago panorama.

  • Finally, you can book a couple's helicopter ride over Chicago.

Have a spa day at AIRE Ancient Baths


The image is taken from their website (

Want to mark Valentine’s Day by sharing a relaxing and rejuvenating experience with your significant other?

Book a spa day at AIRE Ancient Baths!

Spend quality time in each other's company as you share refreshing massages and exfoliating facials.

Soak in the goodness in a sauna or a thermal pool, inspired by ancient traditions from Rome and Greece.

AIRE has a special Valentine's Day package that should leave you feeling refreshed and connected with each other.

Celebrate your love with a luxurious spa day at AIRE Ancient Baths!

Website: Visit the website

Location: Check address/Plan route on Google Maps

Inquiry form: Visit their contact page

Phone: (312) 312-9610


They make everything better, don’t they?

Want a uniquely adorable experience on February 14th?

Head to Cuddle Bunny with your special person.

Bond with one another over a shared love of cute and fluffy creatures.

Pet the lovable rabbits, get a picture taken with them, and even get to feed them.

If you want to keep Valentine's Day low-key, a visit to Cuddle Bunnies is just what you're looking for!

Website: Visit the website

Location: Check address/Plan route on Google Maps

Inquiry form: Scroll down their home page

Phone: (773) 687-9253

Have a cozy dinner inside a rooftop igloo at The Godfrey


The image is taken from their website (

Looking for a Valentine’s Day dinner where you can get a little cozier than at a typical restaurant/cafe?

Book a rooftop igloo at The Godfrey!

Imagine yourself snuggling up against your special someone, even as you watch the snow fall all around you.

Nope, this isn’t a scene from a survival movie - it’s the rooftop igloo dining experience you can expect at the Godfrey Hotel!

Sip on a relaxing cocktail and bite into gourmet creations while soaking in each other’s company.

Rooftop dining is a great way to celebrate the festival of love in Chicago!

Website: Visit the website

Location: Check address/Plan route on Google Maps

Inquiry form: Visit the contact page


Phone: (312) 374-1830

Attend a class


Discover a mutual interest!

Few experiences will bring you together as trying something new as a couple.

Which is what makes attending a class such a good way of enjoying the Valentine’s Day spirit.

Share in the joy of picking up a new skill, or learning a new subject. Support one another through the ups and downs as you try to navigate your class.

Even the discovery of a mutual interest will be a moment you’ll remember fondly for years.

Some classes you can sign up for

Catch a show