32 Things to Do in Chicago for Couples

Things to Do in Chicago for Couples

Chicago, the Windy City, is renowned for its stunning architecture, rich cultural history, and vibrant culinary scene. For couples seeking to explore the city’s offerings, there’s an abundance of activities that cater to all interests and tastes. Whether you’re planning a romantic getaway, celebrating an anniversary, or just looking for a fun date idea, Chicago provides the perfect backdrop for unforgettable moments. This guide will highlight the best things to do in Chicago for couples, from relaxing strolls in beautiful parks to thrilling adventures and cultural experiences. Read on to discover how you can make the most of your time together in this dynamic city.

Things to Do in Chicago for Couples

  1. Stroll Through Millennium Park

Millennium Park is an iconic destination in Chicago, perfect for a romantic stroll. The park spans 24.5 acres and offers various attractions. Millennium Park is a must-visit for couples. The park is home to the famous Cloud Gate sculpture, commonly known as “The Bean.” This large, reflective sculpture is a great spot for taking memorable photos together. The serene Lurie Garden offers a peaceful retreat where you can walk hand-in-hand through beautiful landscapes.

During the summer, the Jay Pritzker Pavilion hosts free concerts and outdoor movies, making for a perfect evening date under the stars. Winter brings a charming ice skating rink to the park, providing a delightful experience for couples who enjoy winter activities. With its art installations, green spaces, and cultural events, Millennium Park is a versatile destination for couples looking to enjoy Chicago’s urban beauty.

  1. Enjoy a River Cruise

Exploring Chicago’s architecture from the water is a unique and romantic experience. A river cruise is an excellent way to see Chicago’s stunning architecture. The Chicago River flows through the heart of the city, offering picturesque views of iconic buildings. Several companies offer guided tours that provide historical insights and interesting anecdotes about the city’s development.

The architecture river cruise is particularly popular, highlighting the work of legendary architects like Frank Lloyd Wright and Mies van der Rohe. For a more intimate experience, opt for a sunset or evening cruise. Watching the city lights reflect off the water as you sip on a glass of wine creates a magical ambiance. Whether you are architecture buffs or simply enjoy being on the water, a river cruise is a memorable activity for couples visiting Chicago.

  1. Dine at Alinea

For couples who appreciate fine dining, Alinea offers an extraordinary culinary experience. Alinea is not just a restaurant; it’s an experience. Ranked among the best in the world, this three-Michelin-star restaurant offers a multi-course tasting menu that changes with the seasons. Each dish is a work of art, designed to engage all your senses.

The innovative cuisine, crafted by renowned chef Grant Achatz, features unexpected flavor combinations and presentation techniques that surprise and delight. Dining at Alinea is an intimate experience, with a limited number of tables ensuring personalized service. The ambiance is sophisticated yet inviting, making it an ideal spot for a special occasion. While the meal is a splurge, it’s an unforgettable dining adventure that will leave a lasting impression.

  1. Visit the Art Institute of Chicago

The Art Institute of Chicago is a treasure trove of artistic masterpieces, perfect for art-loving couples. The Art Institute of Chicago houses one of the most impressive art collections in the world. As you wander through the museum, you will encounter works by artists such as Van Gogh, Monet, and Picasso. The museum’s vast collection spans centuries and cultures, offering something for every art enthusiast.

Special exhibitions often feature contemporary artists and cutting-edge installations, providing fresh and exciting experiences. The museum’s beautiful setting, with its grand architecture and serene courtyards, enhances the romantic atmosphere. After exploring the galleries, enjoy a coffee at the museum’s café or take a leisurely stroll through the adjacent Grant Park. The Art Institute of Chicago offers a perfect blend of culture and romance for couples.

  1. Take a Walk Along the Chicago Riverwalk

The Chicago Riverwalk is a scenic destination that offers a variety of activities for couples. The Chicago Riverwalk stretches for 1.25 miles along the Chicago River, offering beautiful views and plenty of things to do. Couples can enjoy a leisurely walk, stopping at various points of interest along the way. There are numerous restaurants and bars where you can sit outside and enjoy the river views.

For a bit of adventure, rent a kayak and paddle through the city. Art installations and historical plaques provide interesting insights into Chicago’s past. The Riverwalk also hosts events such as live music and outdoor fitness classes, adding to the lively atmosphere. Whether you are looking for a relaxing stroll or an active outing, the Chicago Riverwalk is a versatile and romantic destination for couples.

  1. Explore Lincoln Park Zoo

Lincoln Park Zoo offers a fun and free outing for couples who love animals and nature. Lincoln Park Zoo is one of the oldest zoos in the country and is open year-round with no admission fee. It is located in the heart of Lincoln Park, providing a green oasis in the bustling city. The zoo is home to a wide variety of animals, from big cats and primates to reptiles and birds.

Strolling through the zoo’s beautifully landscaped grounds, couples can enjoy close-up views of exotic animals and learn about conservation efforts. The zoo also features a charming farm area where you can meet domesticated animals. For a more romantic experience, visit during the zoo’s special events, such as ZooLights during the holiday season, when the entire zoo is transformed with festive light displays. Lincoln Park Zoo offers a delightful and budget-friendly outing for couples.

  1. Relax at a Spa

A spa day offers relaxation and rejuvenation, perfect for couples needing a break from sightseeing. Chicago boasts numerous world-class spas that provide a serene escape from the city’s hustle and bustle. Couples can indulge in a variety of treatments, from massages and facials to aromatherapy and hydrotherapy.

Many spas offer special packages designed for couples, including private suites with side-by-side massage tables and soaking tubs. The Peninsula Spa and Chuan Spa are two popular choices that offer luxurious experiences. Spending a day at the spa allows you to unwind, connect, and recharge. It’s a perfect way to balance out a busy itinerary and ensure you both leave Chicago feeling refreshed and pampered.

  1. Take in a Show at the Chicago Theatre

Watching a live performance at the historic Chicago Theatre is a memorable cultural experience. The Chicago Theatre is an iconic venue known for its grand architecture and rich history. Opened in 1921, the theatre has hosted countless performances, from Broadway shows and concerts to comedy acts and magic shows. Attending a show here is not just about the performance; it’s also about the atmosphere.

The theatre’s ornate design, with its famous marquee and lavish interior, transports you back to a bygone era of entertainment. Couples can choose from a wide variety of shows depending on their interests. After the show, explore the surrounding Theatre District, which offers plenty of dining and nightlife options. Experiencing a live performance at the Chicago Theatre is a perfect blend of culture and romance.

  1. Visit the Chicago Botanic Garden

The Chicago Botanic Garden is a beautiful and tranquil destination for couples who love nature. Located just outside the city, the Chicago Botanic Garden offers 385 acres of stunning landscapes to explore. The garden features 27 distinct gardens, including the Japanese Garden, Rose Garden, and English Walled Garden.

Each garden showcases different plants and design styles, providing a diverse and captivating experience. Couples can stroll along winding paths, enjoy picturesque views of the lakes, and relax on benches tucked away in quiet corners. The garden also hosts seasonal events, such as orchid shows and holiday lights, adding to the romantic atmosphere. A visit to the Chicago Botanic Garden allows couples to immerse themselves in nature and enjoy a peaceful retreat from the city’s pace.

  1. Have Fun at Navy Pier

Navy Pier offers a mix of entertainment, dining, and attractions, perfect for a fun-filled date. Navy Pier is a popular destination that offers something for everyone. Couples can enjoy a ride on the Centennial Wheel, which provides panoramic views of the city and Lake Michigan. The pier is also home to various attractions, such as the Chicago Children’s Museum, IMAX Theatre, and an array of shops and restaurants.

For a romantic meal, dine at one of the waterfront restaurants and enjoy the view. Navy Pier also hosts a variety of events and festivals throughout the year, including fireworks displays in the summer. Whether you are looking for adventure, entertainment, or relaxation, Navy Pier is a lively and dynamic spot for a memorable date.

  1. Wander Through the Chicago Cultural Center

The Chicago Cultural Center is a hidden gem that offers free art exhibitions, performances, and stunning architecture. The Chicago Cultural Center is a must-visit for couples who appreciate art and culture. Located in a historic building, the center is home to beautiful art exhibitions, concerts, and performances, all of which are free to the public.

One of the highlights is the breathtaking Tiffany stained-glass dome, the largest of its kind in the world. The center often hosts lectures, film screenings, and other cultural events, providing a rich and diverse experience. The grand staircases and mosaic-tiled interiors create a romantic atmosphere perfect for leisurely exploration. After visiting the center, couples can enjoy a coffee at one of the nearby cafés or take a short walk to Millennium Park.

  1. Explore the Chicago History Museum

Dive into Chicago’s rich history with interactive exhibits and fascinating stories at the Chicago History Museum. The Chicago History Museum offers an immersive journey into the city’s past. Couples can explore exhibits that cover Chicago’s history from its founding to the present day, including the Great Chicago Fire, the city’s role in the civil rights movement, and its cultural evolution.

Interactive displays and multimedia presentations make the history come alive. The museum also features a charming Victorian-era house, allowing visitors to step back in time. Special exhibitions often showcase unique aspects of Chicago’s history, providing fresh and interesting content. After your visit, take a romantic stroll through the nearby Lincoln Park or enjoy a meal at one of the many nearby restaurants.

  1. Attend a Jazz Show at the Green Mill

Experience Chicago’s rich musical heritage with a live jazz performance at the historic Green Mill. The Green Mill Cocktail Lounge is an iconic venue that offers a nostalgic glimpse into Chicago’s jazz age. Established in 1907, the Green Mill was a favorite haunt of Al Capone and has maintained its classic ambiance.

Couples can enjoy live jazz performances every night of the week, featuring talented local and international artists. The cozy, dimly-lit interior with its vintage décor sets a romantic mood, perfect for an intimate evening. The Green Mill also hosts poetry slams and other events, adding variety to the entertainment. Enjoying a night of smooth jazz at the Green Mill is a quintessential Chicago experience for music-loving couples.

  1. Take a Cooking Class Together

Learn new culinary skills and bond over cooking at one of Chicago’s many cooking schools. Taking a cooking class together is a fun and interactive way for couples to bond. Chicago boasts several top-notch cooking schools that offer classes for all skill levels. The Chopping Block and Cook Au Vin are popular choices, providing hands-on instruction in a variety of cuisines.

Whether you are interested in mastering Italian pasta, perfecting sushi rolls, or exploring pastry making, there is a class for every culinary interest. These classes not only teach valuable cooking skills but also offer a chance to work together and enjoy the fruits of your labor. After the class, you can recreate the dishes at home, adding a personal touch to your culinary repertoire.

  1. Visit the Adler Planetarium

Explore the wonders of the universe and enjoy stunning views of the Chicago skyline at the Adler Planetarium. The Adler Planetarium offers a fascinating and educational experience for couples interested in astronomy and space exploration. Located on the shore of Lake Michigan, the planetarium provides breathtaking views of the city skyline.

Inside, couples can explore a variety of exhibits that cover everything from the history of astronomy to the latest discoveries in space science. The planetarium’s state-of-the-art theaters offer immersive shows that transport you to distant galaxies and star systems. Special events, such as stargazing sessions and lectures by astronomers, add to the enriching experience. A visit to the Adler Planetarium is both enlightening and romantic, making it a perfect date activity.

  1. Discover the 606 Trail

Enjoy a scenic walk or bike ride along the 606 Trail, a repurposed rail line turned green space. The 606 Trail, also known as the Bloomingdale Trail, is a 2.7-mile-long elevated greenway that offers a unique way to explore Chicago’s neighborhoods. Couples can walk, jog, or bike along the trail, which winds through vibrant communities and offers scenic views of the city.

The trail is lined with art installations, gardens, and parks, creating a dynamic and engaging environment. Along the way, you can stop at various entry points to explore local shops, cafes, and restaurants. The 606 Trail provides a peaceful and scenic escape from the city’s hustle and bustle, perfect for an active and enjoyable date.

  1. Enjoy a Comedy Show at Second City

Laugh together at a world-famous comedy show at Second City, Chicago’s premier improv theater. Second City is renowned for its improvisational comedy and has launched the careers of many famous comedians. Attending a show here is a guaranteed way to share some laughs and create fun memories. The theater offers a variety of performances, from classic sketch comedy to innovative improv shows.

The intimate setting ensures that every seat has a great view, and the performers often engage with the audience, making for an interactive experience. Second City’s convenient location in Old Town means you can easily combine the show with dinner or drinks at nearby establishments. A night of comedy at Second City is a delightful and entertaining date option for couples.

  1. Take a Day Trip to Starved Rock State Park

Escape the city for a day and explore the natural beauty of Starved Rock State Park. Located about 90 minutes from Chicago, Starved Rock State Park offers a stunning natural retreat for couples who love the outdoors. The park features 13 miles of hiking trails that wind through picturesque canyons, waterfalls, and woodlands.

Each season brings its own beauty, from spring wildflowers to fall foliage and winter ice formations. Couples can hike, picnic, and enjoy the serene surroundings. The park also offers guided tours and boat rides on the Illinois River. A day trip to Starved Rock State Park provides a refreshing break from city life and an opportunity to connect with nature and each other.

  1. Visit the Garfield Park Conservatory

Explore exotic plants and beautiful gardens at the Garfield Park Conservatory. The Garfield Park Conservatory is one of the largest and most stunning botanical conservatories in the country. Couples can wander through eight different indoor gardens, each showcasing a unique collection of plants from around the world.

The lush, tropical setting is perfect for a romantic stroll, with vibrant flowers, towering palms, and serene water features. The conservatory also hosts seasonal flower shows and special events, providing fresh experiences throughout the year. The outdoor gardens, including the Monet Garden and City Garden, are equally enchanting and offer additional space to explore. A visit to the Garfield Park Conservatory is a peaceful and romantic escape into nature’s beauty.

  1. Experience the Chicago Magic Lounge

Be amazed by close-up magic and theatrical performances at the Chicago Magic Lounge. The Chicago Magic Lounge offers a unique and enchanting evening of entertainment for couples. This venue celebrates the art of close-up magic, with performers showcasing their skills right at your table. The main stage features a variety of magic acts, from classic tricks to modern illusions.

The intimate setting and speakeasy-style décor create a mysterious and romantic ambiance. Guests can enjoy cocktails and small plates while being entertained by talented magicians. The Chicago Magic Lounge provides a captivating and unforgettable experience, making it an ideal date night destination for couples seeking something different and magical.

  1. Take a Helicopter Tour

Experience breathtaking views of Chicago’s skyline and landmarks from above with a helicopter tour. A helicopter tour offers an exhilarating and unforgettable way to see Chicago from a unique perspective. Couples can soar high above the city, enjoying panoramic views of iconic landmarks such as the Willis Tower, Navy Pier, Millennium Park, and Lake Michigan.

Various companies offer different tour packages, including sunset and nighttime flights that highlight the city’s dazzling lights. The experience is both thrilling and romantic, providing a new way to appreciate Chicago’s architectural beauty and urban landscape. The tour is guided by experienced pilots who share interesting facts and stories about the city’s history and landmarks. A helicopter tour is perfect for couples seeking adventure and spectacular views.

  1. Visit the Shedd Aquarium

Discover marine life and enjoy interactive exhibits at the Shedd Aquarium. The Shedd Aquarium is one of the largest indoor aquariums in the world, making it an exciting destination for couples. The aquarium houses over 32,000 animals, including dolphins, sharks, sea otters, and exotic fish. Couples can explore various exhibits that showcase diverse marine ecosystems, from coral reefs to the Amazon River.

The Caribbean Reef exhibit, located in the center of the aquarium, features a 90,000-gallon circular tank where divers interact with marine life. The Oceanarium offers stunning views of the city skyline and Lake Michigan while housing beluga whales and Pacific white-sided dolphins. Interactive experiences, such as touch tanks and behind-the-scenes tours, add to the adventure. A visit to the Shedd Aquarium is both educational and entertaining, perfect for a fun and enriching date.

  1. Enjoy a Rooftop Bar

Relax with a cocktail and enjoy stunning views at one of Chicago’s many rooftop bars. Chicago boasts numerous rooftop bars that offer incredible views of the city’s skyline and Lake Michigan. Couples can enjoy a romantic evening sipping cocktails and savoring delicious small plates while taking in the breathtaking scenery.

Popular rooftop bars include the J. Parker, located atop the Hotel Lincoln, which offers panoramic views of Lincoln Park and the lake, and Cindy’s, which overlooks Millennium Park and the Art Institute of Chicago. Many rooftop bars feature cozy seating, fire pits, and live music, creating a perfect ambiance for a memorable night out. Whether you visit during the day for a sunny brunch or in the evening for a sunset cocktail, Chicago’s rooftop bars provide a chic and romantic setting for couples.

  1. Visit the Museum of Contemporary Art

Explore cutting-edge art and innovative exhibits at the Museum of Contemporary Art. The Museum of Contemporary Art (MCA) Chicago is a hub for modern and contemporary art lovers. Couples can explore a diverse range of exhibits that feature works by emerging and established artists from around the world. The museum’s rotating exhibitions often include multimedia installations, interactive pieces, and thought-provoking works that challenge conventional perspectives.

The MCA also hosts various events, such as artist talks, film screenings, and performances, providing an immersive cultural experience. The museum’s outdoor sculpture garden and terrace offer a tranquil space to relax and reflect. Located near the Magnificent Mile, the MCA is easily accessible, making it a convenient and enriching date destination for art-loving couples.

  1. Go on a Food Tour

Savor Chicago’s culinary delights with a guided food tour through the city’s diverse neighborhoods. A food tour is a fantastic way for couples to explore Chicago’s rich culinary scene. Guided tours take you through various neighborhoods, offering tastings of iconic Chicago dishes and local specialties. From deep-dish pizza and Italian beef sandwiches to gourmet chocolates and craft beers, a food tour provides a delicious and immersive experience.

Popular tours include the Chicago Food Planet tours, which cover areas like Wicker Park, River North, and the West Loop. Along the way, knowledgeable guides share stories about the city’s history, culture, and food traditions. A food tour is a fun and flavorful way to discover new tastes and enjoy a shared culinary adventure.

  1. Sail on Lake Michigan

Embark on a romantic sailing adventure on Lake Michigan. Sailing on Lake Michigan offers a serene and picturesque escape from the bustling city. Couples can charter a private sailboat or join a group sailing tour to enjoy the tranquil waters and stunning views of Chicago’s skyline.

Many companies offer sunset sails, which provide a romantic setting as the sun dips below the horizon, casting a golden glow over the city. For a more interactive experience, consider taking a sailing lesson together. Sailing on Lake Michigan is a relaxing and enjoyable way to spend quality time together, surrounded by the beauty of nature and the city.

  1. Explore the Field Museum

Discover natural history and ancient artifacts at the Field Museum. The Field Museum is one of the largest natural history museums in the world, offering a wealth of exhibits that fascinate and educate visitors. Couples can explore the museum’s extensive collection, which includes dinosaur skeletons, ancient Egyptian artifacts, gemstones, and cultural exhibits from around the globe.

The museum’s most famous resident, Sue the T. rex, is a must-see highlight. Interactive exhibits and immersive displays bring history and science to life, providing a captivating experience for visitors of all ages. The museum also offers special exhibitions and events, ensuring there’s always something new to discover. Located in Grant Park, the Field Museum is a perfect destination for a day of exploration and learning.

  1. Attend a Sporting Event

Cheer on your favorite team at a Chicago sporting event. Chicago is home to several professional sports teams, offering couples a chance to experience the excitement of live sports. Whether you’re a fan of baseball, basketball, football, or hockey, there’s a game for everyone. Catch a Cubs game at the historic Wrigley Field, or head to Guaranteed Rate Field to see the White Sox in action.

For basketball and hockey enthusiasts, the United Center hosts the Chicago Bulls and Chicago Blackhawks. Attending a game provides an electric atmosphere, with enthusiastic fans, thrilling plays, and plenty of entertainment. It’s a great way to share in the city’s sports culture and create lasting memories together.

  1. Visit the Peggy Notebaert Nature Museum

Explore interactive exhibits and enjoy the butterfly haven at the Peggy Notebaert Nature Museum. The Peggy Notebaert Nature Museum is a delightful destination for couples who love nature and science. The museum features interactive exhibits that explore the natural world, with a focus on the ecosystems of the Chicago region.

One of the highlights is the Judy Istock Butterfly Haven, a tropical greenhouse that houses hundreds of live butterflies. Walking through the haven, surrounded by fluttering butterflies and lush plants, creates a magical and romantic experience. The museum also offers outdoor nature trails, where couples can enjoy a peaceful walk and observe local wildlife. Located in Lincoln Park, the Peggy Notebaert Nature Museum is a charming and educational destination for a date.

  1. Take a Segway Tour

Discover Chicago’s landmarks and attractions on a fun and informative Segway tour. A Segway tour offers a unique and enjoyable way to explore Chicago’s top sights. Couples can glide through the city’s streets and parks, covering more ground than on a walking tour. Guided Segway tours provide interesting commentary on Chicago’s history, architecture, and culture, making the experience both fun and educational.

Popular routes include tours along the lakefront, through Grant Park, and around the Museum Campus. Riding a Segway is easy to learn, and the experience is both exciting and relaxing. A Segway tour is a perfect blend of adventure and sightseeing, offering couples a memorable way to see the city.

  1. Visit the Frank Lloyd Wright Home and Studio

Explore the architectural genius of Frank Lloyd Wright with a tour of his home and studio. The Frank Lloyd Wright Home and Studio in Oak Park, just outside of Chicago, offers an intimate look into the life and work of one of America’s greatest architects. Couples can take a guided tour of Wright’s home, where he lived and worked from 1889 to 1909. The tour provides insights into his innovative designs and architectural philosophy.

The studio, where Wright developed many of his early masterpieces, showcases his creative process and unique approach to architecture. The surrounding neighborhood features several other Wright-designed homes, making it an ideal destination for an afternoon of exploration. A visit to the Frank Lloyd Wright Home and Studio is a must for architecture enthusiasts and provides a fascinating glimpse into the mind of a visionary artist.

  1. Enjoy a Picnic in Grant Park

Relax with a picnic in the scenic and expansive Grant Park. Grant Park, often referred to as “Chicago’s front yard,” offers a beautiful and expansive setting for a romantic picnic. Couples can find a cozy spot on the lush lawns, near Buckingham Fountain, or along the lakefront. Pack a picnic basket with your favorite snacks and beverages, and enjoy a leisurely meal surrounded by nature and stunning views of the city skyline.

The park also features several gardens, sculptures, and walking paths, providing plenty of opportunities for a post-picnic stroll. During the summer months, Grant Park hosts various events and festivals, adding to the lively and vibrant atmosphere. A picnic in Grant Park is a simple yet charming way to spend quality time together in the heart of Chicago.


Chicago is a city that thrives on diversity, offering a plethora of activities that cater to every couple’s unique preferences. From exploring world-class museums and dining at exquisite restaurants to enjoying serene outdoor spaces and engaging in exciting adventures, the Windy City has something to enhance every romantic experience. Whether you’re locals looking to rediscover your city or visitors eager to explore, these top things to do in Chicago for couples will ensure you create lasting memories with your special someone. So pack your bags, plan your itinerary, and get ready to fall in love with Chicago all over again.

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