DEC 2023

Explore love's journey with Chicago's top romantic experiences for couples.

Welcome to the heart of romance in the Midwest! 

If you're scouring the web for things to do for couples in Chicago, you've hit the jackpot. 

Whether it's your first date or your hundredth, Chicago's vibrant streets are bustling with opportunities for love and adventure. 

From the cozy corners of quaint cafes to the thrilling heights of skyscrapers, this city is a treasure trove of romantic experiences. 

So, grab your partner's hand, and let's dive into the ultimate guide to creating unforgettable memories in the Windy City!

Restaurant Row on Randolph Street

Couple holding hands at a romantic dinner.

Savor love and cuisine on Randolph Street – Chicago's top dining destination! Representational image.

Whether you’re looking for a casual dinner date or an elegant rendezvous with your significant other, you can’t go wrong with Restaurant Row.

From the cozy Italian ambiance of Avec to the sophisticated flair of Girl & the Goat, this stretch of the West Loop offers a smorgasbord of dining options. 

Whether seeking famous Chicago foods or overseas fare, you’ll find what you’re looking for here.

As you’ll be competing with numerous other couples in Chicago, book your table in advance, especially during weekends. 

And check for dress codes, which vary from casual to smart casual.

End your evening with a romantic stroll down Randolph amidst the twinkling lights and vibrant energy of our city.

Fox in a Box Escape Rooms (that’s us!)

Couple enjoying a romantic and challenging adventure inside our escape room.

Unlock love and adventure in our escape rooms!

Yearning for a thrilling adventure with your better half? At Fox in a Box Chicago, we offer a unique blend of excitement and teamwork that’s perfect for a romantic experience. 

Our escape rooms, like The Bank and Zodiac, are must-try group activities for adults

As you navigate through puzzles and challenges, you'll find common energies and feel the excitement of taking on problems together - a key step to deepening a relationship. 

And once the game ends, expect a little memento from your game master.

Located in the Dearborn Galleria, we’re the best escape room in Chicago, and an outing with us will leave you and your partner with lasting memories. 

Website: Visit our home page

Location: Plan your route via Google Maps

Phone: (312) 878-7899

AIRE Ancient Baths

Couple enjoying a relaxing spa massage in Chicago.

Rejuvenate with your loved one at Aire Ancient Baths! Representational image.

Imagine soaking with your cutie pie in thermal baths, feeling the stress melt away, and connecting in a serene, candle-lit atmosphere.

Located in a beautifully restored 1902 factory in River West, AIRE is a distinct medley of history and wellness

The original exposed brick, wooden beams, and industrial columns of the building form an intimate setting where you can immerse yourself in traditional Roman, Greek, and Ottoman bathing experiences.

Aire also offers various massages and rituals for relaxation and rejuvenation. 

With special offerings like the 'Escape Together' or 'Love Connection' which offer truly unique experiences, AIRE is one of the most preferred Chicago indoor activities for couples. 

Especially during these stressful times, a visit to Aire Ancient Baths is a memorable way to celebrate your relationship. 

Website: Visit their website

Location: Plan your route via Google Maps

Phone: (312) 312-9610

Chicago Murder Mystery Tour by Magnifico Tours

Deserted backstreet in Chicago setting the perfect mystery scene.

Investigate the mysteries of the Windy City as a team!

Are you and your partner fascinated by Chicago's storied past and unsolved mysteries?

Check out the Murder Mystery Tour by Magnifico Tours.

The brainchild of Northwestern alum André Baronov-Torres, this tour combines the thrill of a detective game with exploring Chicago's historic Gold Coast and is perfect for couples who love a dash of mystery.

You'll journey through iconic sites, gaining exclusive access and uncovering secrets and stories that range from Al Capone to the Playboy Mansion. 

The entire experience lasts 2 hours, and multiple tours are available daily, promising an unforgettable experience. 

Whether you're a true-crime aficionado or just craving a unique date, this interactive and engaging tour will bring a new dimension to your romantic escapades in Chicago.

Website: Visit their website

Phone: (872) 310-7645

Ice skating in Maggie Daley Park

Ice skating for couples at Maggie Daley Park.

Discover romance on the ice at Maggie Daley Park! Representational image.

Gliding through Alpine trees and “mountains” (the climbing wall), ice skating at Maggie Daley Park is not just a winter activity; it's a magical experience for couples in Chicago. 

Enjoy stunning views of the city skyline as you skate along the winding trail.

Open from November to March, it’s a must-visit destination for a whimsical winter date - that’s part of the reason it’s a Midwestern attraction.

Not a seasoned skater? Don’t worry - You’re not alone!

In fact, some say that holding on to your partner amidst the wintry wonderland all around adds to the romantic allure.

Skate rentals are available on-site. And you can warm up afterward with a hot chocolate from the nearby Park Cafe.

Website: Visit their website

Location: Plan your route via Google Maps

Phone: (312) 552-3000

Signature Dinner Cruise on Lake Michigan

Enjoy the cruise on Lake Michigan, with stunning views of the Chicago skyline at night.

Experience romance under the stars on the Signature Dinner Cruise.

Step aboard a remarkable evening with the Signature Dinner Cruise on Lake Michigan.

With spacious decks for strolling and cozy tables for intimate dining, they pull out all the stops to make it a meaningful experience.

It's more than just a meal or a cruise; it's one of the top attractions for young adults in Chicago.

Gaze at the city lights twinkling in the water and have meaningful conversations - or just enjoy each other’s company. 

And take a selfie or two to capture memories of your experience.

Website: Visit their website

Check out a farmers' market

Fresh produce at a farmers' market in Chicago.

Discover fresh delights together as you stroll through our city’s farmers markets.

Transform a typical lazy Sunday morning into a meaningful bonding experience at a farmers' market in Chicago. 

It's a simple yet rewarding outing that requires minimal planning, offers a chance to complete your grocery shopping, and supports local farmers and the community. 

Share moments of discovery and delight amidst the colors and scents of fresh produce, artisanal foods, and handmade crafts.

Wondering which one to choose?

There are numerous options for you to choose from, including:

  • Logan Square Farmers Market: A community-centric spot where you can meander among local artisans and enjoy fresh, seasonal goodies.

  • Maxwell Street Market: Dive into a lively and colorful atmosphere, perfect for couples who enjoy exploring diverse cultures and tasting unique street foods.

  • Daley Plaza City Market: Nestled in the city's heart, it’s a romantic destination for those who appreciate urban charm mixed with fresh, local produce.

  • Green City Market: Ideal for health-conscious couples, offering a range of organic and sustainable goods in a serene environment.

Meet up for coffee

Couple enjoying a cozy coffee date in a quaint Chicago cafe.

Discover Chicago's cozy cafes together!

Cafes have been a beloved meeting spot for people in love for decades.

They’re more than just a caffeine fix; they offer a blend of warmth, conversation, and connection - making them a way to destination on Valentine’s Day in Chicago.

And Chicago's cafes provide intimate settings ideal for nurturing romance, whether over a latte, a pastry, or amidst the shelves of a book cafe, each spot has its own charm. 

Top Chicago cafes for your next date

  • Volumes Bookcafe: A haven for book and coffee lovers, this cafe offers a quiet, literary atmosphere for deep conversations and shared interests.

  • Pierrot Gourmet: This European-style cafe is perfect for those seeking a touch of sophistication with their coffee, offering delicious pastries in an elegant setting.

  • Geja's Cafe: Known for its cozy ambiance, it's a great place to enjoy a warm beverage and intimate conversations in a romantic setting.

  • Ludlow Charlingtons Coffee Shop: A family-owned place founded during the 2020 pandemic, this cafe is known for its community spirit and efforts in supporting local dog shelters.

The Bean

The reflective Cloud Gate sculpture, known as The Bean

Would make for terrific couple selfies, don’t you think? #thebean #couples #chicago

We know. 

Checking out The Bean doesn't sound like much of an activity for lovebirds in Chicago…But hear us out. 

Anish Kapoor’s famous sculpture is the perfect spot for an impromptu, spontaneous meet-up with your significant other. 

Maybe a quick rendezvous during your lunch break, especially if your office is nearby, or a sudden decision to meet up and enjoy the city vibe.

Selfies at The Bean are a fun, modern twist to your usual date photos and great for social media-enthusiastic couples. 

Sharing a laugh while trying to get the perfect angle can be a surprisingly intimate experience.

Want to extend the date? Many downtown Chicago attractions, like Lurie Garden in Millennium Park and The Chicago Cultural Center, are within walking distance.

Website: Visit its website

Location: Plan your route via Google Maps

Drink in the Chicago skyline over cocktails at Cindy’s

A panoramic view of the Chicago skyline at Cindy's.

A toast to love above the Windy City's skyline. Representational image.

Imagine clinking glasses with your partner amidst a refreshing breeze while gazing at our city’s many wonders, including Millennium Park and The Bean. 

To top that up, Cindy's offers a selection of carefully crafted cocktails and a menu highlighting fresh, local ingredients - ideal for a sophisticated yet relaxed evening.

For those who love sharing their moments, the stunning views provide the perfect backdrop for selfies.

So, if you’re planning a romantic evening that combines good drinks, great views, and even better company, Cindy’s is your go-to spot.

Website: Visit their website

Location: Plan your route via Google Maps

Phone: (312) 792-7502

Browse the titles at the Last Chapter Book Shop