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Home » 10 Romantic Things to Do in Chicago for Couples (By a Local)

10 Romantic Things to Do in Chicago for Couples (By a Local)

Neon lit entrance of Zanies Comedy Club

Are you and your partner planning a romantic getaway to Chicago? Look no further, as the Windy City has plenty of incredible experiences in store for couples. I’ve lived in Chicago for more than 12 years but I’m yet to run out of experiences to enjoy with my husband. Read on for the ten best things to do in Chicago for couples and create unforgettable memories in the Windy City.

From enchanting sunrises on the harbor to delightful comedy shows and captivating theater performances, Chicago offers a diverse range of activities perfect for two. Immerse yourselves in the city’s rich architectural history, indulge in delicious world cuisine (and the famous deep-dish pizza), and take romantic walks along Lake Michigan. You can also paddle along the picturesque Chicago River or enjoy a tranquil picnic in one of the city’s beautiful parks.

In Chicago, the possibilities for creating cherished moments with your partner are endless, ensuring that your time together is nothing short of extraordinary.

1. Watch drama at the Theatre

Ornate interiors of James M. Nederlander Theatre
Inside the James M. Nederlander Theatre in Chicago Theatre District

Chicago’s vibrant theatre scene makes it a must-visit destination for theater enthusiasts and couples looking for a memorable cultural experience. Nestled in the heart of downtown, the Theatre District boasts a collection of historic and contemporary theaters that showcase an array of captivating dramas, musicals, and thought-provoking performances.

From the iconic Chicago Theatre to the intimate venues of Steppenwolf and Goodman Theatre, the city offers a diverse range of productions to suit every taste. Immerse yourself in the magic of live theater as you witness talented actors bring stories to life on stage, surrounded by the electric atmosphere that permeates the district.

My personal favorite is Goodman where I’ve watched Chekov’s classics Uncle Vanya and The Cherry Orchard with my husband. Whether it’s a classic play or an avant-garde production, watching theater in Chicago is an immersive experience and one of the best things to do in Chicago for couples.

2. Share a laugh at a comedy show

Walls lined with old photographs of comics at Zanies Comedy Club
Walls showing the rich history of Zanies Comedy Club

The Windy City is easily the comedy capital of the Midwest. Chicago is renowned for its thriving comedy scene, making it an ideal destination for couples seeking a night filled with humor and entertainment. It is home to numerous comedy clubs and venues that showcase a diverse range of comedic styles, from stand-up to improv.

From world-famous venues like The Second City and iO Theater to hidden gems scattered across the city, there’s a comedy show for every taste. I’ve been to several comedy clubs in the city but there’s a special place in my heart for Zanies Comedy Club. It is such an intimate gathering where you can feel the energy of the artists and watch the rich history of the club staring back at you from the walls. They have very reasonable ticket prices for the kind of talent they bring along with a two-item minimum of food or drinks per person.

So grab your partner’s hand, get ready for a night of laughter, and let the comedians of Chicago entertain you with their comedic genius and infectious energy. It’s a guaranteed recipe for a memorable and laughter-filled date night!

3. Catch an indie movie or Film Festival

Steps leading inside the Gene Siskel Film Center
The sleek interiors of the Gene Siskel Film Center

For cinephile couples looking for a unique and captivating movie experience, Chicago offers a haven for independent film lovers. One must-visit destination is the Gene Siskel Film Center, a renowned hub for independent, international, and classic films. You might have heard a lot about the Art Institute of Chicago, but not many are familiar with this film center which is the public program of the School of the Art Institute of Chicago.

Nestled in the heart of the city, this intimate venue showcases a curated selection of thought-provoking movies from around the world. From powerful documentaries to avant-garde experimental films and everything in between, the Gene Siskel Film Center presents an eclectic range of cinematic gems that will spark meaningful conversations. This makes it one of the best things to do in Chicago for couples. I loved watching The Eight Mountains here and it’s now one of my all-time favorite movies.

Additionally, Chicago hosts several film festivals throughout the year, including the Chicago International Film Festival, Chicago South Asian Film Festival, and Chicago Underground Film Festival. These festivals celebrate the art of filmmaking by showcasing a diverse array of innovative and boundary-pushing works from across the globe.

Attending an indie movie screening at the Gene Siskel Film Center or immersing yourselves in the vibrant atmosphere of a film festival is a perfect way to discover hidden cinematic gems and appreciate the art of storytelling on the big screen together.

4. Enjoy a beautiful sunrise or sunset on the harbor

Silhouette of trees and person during sunrise at Belmont Harbor
Vivid colors of sunrise at Belmont Harbor

There are few sights in nature as gorgeous as sunrise and sunset. The city’s strategic location on the shores of Lake Michigan provides a stunning backdrop for nature’s daily spectacle.

Whether you choose to witness the vibrant colors of dawn breaking over the skyline or the golden hues of the sun sinking below the horizon, Chicago offers numerous spots to enjoy these magical moments.

Head to the lakefront and find a cozy spot on the sandy beaches, picturesque parks, or harbors like North Avenue Beach, Montrose Beach, or Belmont Harbor. As the sky transforms into a breathtaking canvas of colors, revel in the tranquility and beauty surrounding you.

While the lake is to the east, sunsets in Chicago can be equally fantastic too. The sun disappears into the city and on a gorgeous day leaves streaks of pink and purple. These in turn reflect from the lake and glass-covered high-rises in the east turning the entire sky into a celebration of colors.

5. Walk along Lake Michigan

Chicago skyline view from the lakefront
Chicago skyline view from the lakefront near Adler Planetarium

Walking along Lake Michigan in Chicago is a serene and romantic experience that will deepen your connection and leave you longing for more cherished moments in this captivating city.

Take your partner’s hand and embark on a long walk along the captivating shores of Lake Michigan in the heart of the city. There are several options to enjoy the public lakefront with stunning skyline views from Diversey Harbor in the north to Navy Pier and Adler Planetarium Skyline Walk in the south.

As you stroll along the picturesque lakefront, the city’s skyline provides a breathtaking backdrop to your intimate journey. Feel the cool breeze from the lake gently brushing against your skin as you listen to the rhythmic lapping of the waves.

6. Have a picnic in the park

Cherry blossoms near the lotus-petal sculpture by artist-singer Yoko Ono
Cherry blossoms near the lotus-petal sculpture by artist-singer Yoko Ono in Jackson Park

Escape the bustling city streets and indulge in a tranquil and romantic picnic in one of Chicago’s beautiful parks. Whether you choose the iconic Grant Park, the serene Lincoln Park, the picturesque Millennium Park, or the cherry-blossom-filled Jackson Park, you’re in for a delightful experience. Spread out a cozy blanket, unpack a basket filled with delicious treats, and savor the flavors while surrounded by nature’s beauty.

Handpick the ingredients from a neighboring grocery store. Or grab easy-to-eat sandwiches, wraps, and beverages from restaurants like Cubaneo, Kala Modern Greek, and Goddess and the Baker for a perfect outdoor meal.

Bask in the warm sunshine, listen to the cheerful chirping of birds, and feel the gentle breeze rustling through the trees. A picnic is a beautiful way to slow down on vacation and enjoy the summer weather as the locals do.

7. Kayak along the Chicago River

Green and yellow kayaks resting along the river banks
Paddle these eye-catching kayaks with your partner in downtown Chicago

Discover a unique way to explore Chicago’s vibrant urban landscape by embarking on a kayaking adventure along the Chicago River. You can stick to downtown like most tourists and paddle alongside architectural marvels, soaring skyscrapers, and the vibrant energy of the city.

Take in the breathtaking views of iconic landmarks such as the Willis Tower, the Wrigley Building, and the Tribune Tower with Urban Kayaks. Feel the urban pulse as you navigate the river’s bends and curves, passing under historic bridges and witnessing the bustling riverfront activity.

Or you can get off the beaten path and head to Wild Mile Chicago, the first-ever mile-long floating eco-park in the world. Book a 2-hour REI kayak tour to explore the Wild Mile with two departures each day from their Lincoln Park location.

As you paddle through this urban oasis, you’ll feel a sense of serenity and connection with nature and with each other, making it a truly unforgettable, romantic experience for couples seeking an adventurous date in the heart of the city.

8. Learn about the city’s architecture and history

Chicago skyline as seen from a cruise boat
View of Chicago Skyline as seen from the Lake at Mercury’s Urban Adventure Cruise

Known for its iconic skyline and rich architectural history, the Windy City offers a unique opportunity to explore its architectural wonders from the comfort of a cruise boat. Discovering the city’s resilient history and architecture is one of the best things to do in Chicago for couples. As you glide along the Chicago River, knowledgeable guides will unveil the stories behind the city’s renowned buildings, from historic landmarks to modern marvels.

Marvel at the magnificent structures designed by legendary architects like Frank Lloyd Wright, Ludwig Mies van der Rohe, and Jeanne Gang. Witness the interplay of glass, steel, and concrete that defines Chicago’s architectural landscape.

From the iconic Willis Tower to the sleek Aqua Tower, each building has a tale to tell. The architecture cruise not only educates but also allows you to appreciate the beauty and significance of these structures from a unique vantage point. So, sit back together, relax, and let the architectural wonders of Chicago unfold before your eyes as you embark on this extraordinary voyage of discovery.

9. Relish world cuisine (or deep-dish pizza)

Fish fry with a side of rice and salad
Sampling Kerala Cuisine at Thattu is one of the best things to do in Chicago for couples

Chicago is a culinary haven that extends far beyond its renowned deep-dish pizza. But let’s get the deep-dish pizzas out of the way first. It’s amusing how all of my friends and family visiting Chicago can’t wait to try the deep dish whereas I (and several locals) only ever share a slice of this rich pizza when we have visitors. But hey, no judgment here! While there are primarily three deep dish camps of Uno’s, Giordano’s, and Lou Malnati’s, locals usually head to places like Pequod’s and The Art of Pizza.

But romance doesn’t have to be cheesy like the deep dish. The city boasts a diverse and thriving food scene that embraces unique flavors from around the globe. From upscale fine dining establishments to casual eateries and food trucks, Chicago offers an abundance of world cuisines to satisfy your taste buds.

One of the best things to do in Chicago for couples is to embark on a gastronomic adventure as you explore the city’s neighborhoods, each offering its own culinary treasures. Indulge in flavorful Mexican tacos in Pilsen, savor aromatic South Asian dishes on Devon Avenue and elsewhere, delight in authentic dim sums in Chinatown, or sample mouthwatering Ethiopian dishes in Uptown. Whether you’re a fan of Thai, Korean, Greek, or Middle Eastern cuisine, Chicago has it all. So, set off on a self-guided food tour and discover the richness and diversity of world flavors that await you in the Windy City.

10. Raise a toast at a no-wifi book bar

For couples seeking a unique and cozy spot to unwind, Kibbitznest Books, Brews & Blarney is the perfect destination in Chicago. This charming, no-wifi book bar offers a nostalgic and intimate atmosphere where you can raise a toast to your love.

Leave behind the distractions of technology as you step into a space filled with shelves of thought-provoking books, inviting you to dive into captivating stories and engage in meaningful conversations.

Attend local events like storytelling, comedy shows, and liberal arts discussions hosted in this gem of a place. Check out their events calendar and grab a ticket for your travel dates. You can order some nosh or bring your own food as long as you’re mindful of the minimum spending requirements.

Sip on a carefully crafted cocktail or choose from a selection of craft beers while you and your partner bask in the warm ambiance of Kibbitznest. Toast to your relationship, to the joy of literature, and to the moments of togetherness shared in this cozy haven.


The city truly offers a treasure trove of experiences for couples looking to create unforgettable memories. From the captivating performances at the theater to the laughter-filled comedy shows, the city’s vibrant arts scene promises moments of entertainment and connection. Witnessing a breathtaking sunrise on the harbor or immersing yourselves in thought-provoking indie movies and film festivals adds a touch of magic to your time together.

Walking hand in hand along the beautiful shores of Lake Michigan and indulging in a romantic picnic in one of the city’s picturesque parks allows you to escape into a world of tranquility and romance. Embarking on a kayaking adventure along the Chicago River offers a unique perspective of the city’s architecture and natural beauty.

Exploring the city’s rich history and architectural wonders, while savoring the diverse world cuisine or relishing a deep-dish pizza, allows you to immerse yourselves in Chicago’s cultural tapestry. Finally, raising a toast to your love at a no-wifi book bar adds a touch of nostalgia and connection to your journey.

That’s my curated list of the best things to do in Chicago for couples. Aside from these, keep an eye out for seasonal Chicago events that align with your interests when planning your trip.

Whether you are a local or a visitor, I’d love to hear your favorite Chicago hangouts and experiences in the comments below!

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