33 Date Night Activities in Chicago for Couples and Newlyweds
Chicago is a city that offers endless opportunities for adventure and romance, making it the perfect place for newlyweds to explore and enjoy each other’s company. Whether you're looking for something laid-back and cozy or a fun-filled night of laughter and competition, Chicago has it all. From classic romantic outings to quirky, off-the-beaten-path activities, there's no shortage of date night ideas to make your evening memorable. Here’s a list of some of the best date night activities in Chicago that are sure to add excitement and charm to your newlywed life.
1. Duck Pin Bowling and Milkshakes at Pink Squirrel
Looking for a nostalgic yet unique twist on bowling? Head to Pink Squirrel in Logan Square for a fun and cozy night of duck pin bowling. Unlike traditional bowling, duck pins are smaller, and the balls are much lighter, making the game easier and more playful for all skill levels. The vibrant retro ambiance, complete with neon lights and comfy seating, creates a relaxed atmosphere perfect for enjoying drinks and good conversation between rounds. Add in a delicious cocktail from their creative menu, and you've got a date night to remember.
Address: 2521 N Milwaukee Ave, Chicago, IL 60647
2. Ping Pong at Ace Bounce
If you’re looking to add some competitive spirit to your date night, Ace Bounce is a great place to do so. This upscale ping pong bar offers a lively environment where you can enjoy friendly matches while sipping on cocktails and munching on tasty snacks. Whether you’re a seasoned player or a newbie, it’s a fun and interactive way to spend quality time together. The playful atmosphere combined with the modern design of the space makes for a perfect night of laughter and bonding.
Address: 230 N Clark St, Chicago, IL 60601
3. Darts at Flight Club
For something both competitive and social, visit Flight Club, a modern darts lounge in the River North neighborhood. Flight Club has reimagined the classic game of darts with a stylish, high-tech twist. You and your partner can enjoy a variety of games while sipping on cocktails and enjoying their delicious bar food. The ambiance is both sophisticated and laid-back, creating a perfect backdrop for an evening of friendly competition.
Address: 111 W Hubbard St, Chicago, IL 60654
4. Fondue at Geja’s Café
For a truly romantic date night, Geja’s Café is the place to go. This intimate fondue restaurant in Lincoln Park is known for its cozy, dimly lit atmosphere and exceptional service. You and your partner can dip delicious cheeses, fresh vegetables, and succulent meats into warm fondue pots, while enjoying a bottle of wine or champagne. Geja’s has been a Chicago favorite for years, offering a perfect blend of romance and indulgence for newlyweds looking to savor every bite.
Address: 340 W Armitage Ave, Chicago, IL 60614
5. Jazz Music at Dorian’s
If you and your partner appreciate great live music, Dorian’s is the ideal spot. This intimate jazz bar in the Gold Coast area offers an upscale experience with live performances that set a sophisticated, romantic tone. The cozy space, combined with expertly crafted cocktails and a timeless ambiance, creates a perfect setting for a memorable date night. Whether you're there for the live jazz or just to unwind, Dorian’s provides a perfect escape into the world of smooth melodies and charming conversation.
Address: 659 W Armitage Ave, Chicago, IL 60614
6. Shuffleboard at Royal Palms
For a fun yet low-key evening, head over to Royal Palms Shuffleboard Club in Logan Square. This retro-inspired bar and shuffleboard hall lets you enjoy classic shuffleboard in a vibrant setting, complete with tropical-themed decor. You and your partner can play a few rounds of shuffleboard, sip on cocktails, and enjoy the lively, upbeat atmosphere. Royal Palms also has delicious food and drinks to keep you fueled for the competition.
Address: 1758 W Cortland St, Chicago, IL 60622
7. Pizza Making Class at Pizzeria Uno
For pizza lovers, a hands-on pizza-making class at Pizzeria Uno is a perfect date activity. Pizzeria Uno is famous for its deep-dish pizza, and now you can learn how to make it yourself. During the class, you and your partner will get a step-by-step guide to making the perfect pizza, from the dough to the toppings. It’s a fun, interactive way to bond over your shared love of food, and you get to enjoy the delicious results at the end!
Address: 29 E Ohio St, Chicago, IL 60611
8. Tandem Bike Ride at Bike and Roll Chicago
Explore Chicago from a new perspective by renting a tandem bike at Bike and Roll Chicago. Take a leisurely ride along the lakefront trail or around the city’s iconic landmarks. Riding a tandem bike is a great way to connect with your partner while getting some fresh air and seeing the sights. Whether you’re cycling along the waterfront or through a park, the experience is both fun and romantic.
Address: 239 E Randolph St, Chicago, IL 60601
9. Exhibits at the Color Factory Chicago
If you’re looking for a playful and immersive date experience, the Color Factory is a must-see. This interactive exhibit is full of vibrant colors, whimsical installations, and photo-worthy moments. It’s a lighthearted, fun activity where you and your partner can explore together, enjoying the visual art and quirky displays. It's a perfect way to let your creative side shine while spending quality time with each other.
Address: 6 E Ohio St, Chicago, IL 60611
10. Improv Comedy at Second City
For a night full of laughter and surprise, head to the legendary Second City for a live improv comedy show. This iconic theater has produced some of the best comedians in the world, and their shows are always fresh, funny, and filled with unpredictable moments. Enjoy a night of comedy while sitting back and relaxing in the intimate theater. It’s a great way to laugh together and enjoy Chicago’s famous comedy scene.
Address: 1616 N Wells St, Chicago, IL 60614
11. Bocce at the Athletic Association
For a more relaxed but still competitive night out, visit the Athletic Association’s Game Room for some bocce. This stylish lounge offers both a fun game of bocce and an elegant atmosphere to sip on drinks and unwind. The cozy vibe and playful environment make it an ideal spot to enjoy a casual evening with your partner. Whether you’re experienced or a complete beginner, bocce is a great way to bond and have fun together.
Address: 111 N Wabash Ave, Chicago, IL 60602
12. Music at Howl at the Moon
If you're in the mood for a lively and energetic night, Howl at the Moon is the place to be. This vibrant bar offers an exciting mix of live music, dancing, and large cocktails, creating a high-energy atmosphere perfect for letting loose. With its fun party vibe and upbeat crowd, Howl at the Moon is a great option for newlyweds who want to let their hair down and enjoy a carefree night together.
Address: 26 W Hubbard St, Chicago, IL 60654
13. Mini Golf at Big Mini Putt Club
For a playful and quirky date, mini golf at Big Mini Putt Club is sure to hit the mark. This indoor mini-golf course is located in the heart of the West Loop and offers a fun twist on the traditional mini-golf experience. With neon lights, creative course designs, and a lively atmosphere, it’s the perfect place to share some laughs and friendly competition while enjoying a unique take on this classic date activity.
Address: 1227 W Lake St, Chicago, IL 60607
14. Movie at ChiTown Drive-In
Take your date night outdoors with a visit to ChiTown Drive-In, Chicago’s premier outdoor movie theater. Snuggle up in your car, grab some snacks, and enjoy a movie under the stars. The nostalgic vibe of a drive-in combined with modern technology and comfort creates a charming and relaxed date experience. This is a perfect way to enjoy a classic date activity with a bit of a twist.
Address: 2441 N Lincoln Ave, Chicago, IL 60614
15. Drinks at Three Dots and a Dash
For a tropical escape in the heart of the city, visit Three Dots and a Dash, one of Chicago's best tiki bars. This hidden gem offers exotic cocktails, vibrant decor, and an intimate atmosphere, making it an ideal place for a romantic drink with your partner. The menu is full of creative cocktails made with rum and fresh ingredients, and the speakeasy vibe adds an extra element of intrigue to your night out.
Address: 435 N Clark St, Chicago, IL 60654
16. Arcade Games at Logan Arcade
For a nostalgic and fun-filled night, visit Logan Arcade, where you and your partner can enjoy classic arcade games in a laid-back environment. With a variety of retro games, pinball machines, and more, Logan Arcade offers hours of entertainment. It’s a perfect choice for newlyweds who want to relive their childhood memories while sharing some laughs and playful competition.
Address: 2410 W Armitage Ave, Chicago, IL 60647
17. Visit the Museum of Illusions
For a mind-bending and interactive date, the Museum of Illusions is a fun spot to visit. This unique museum features optical illusions, holograms, and interactive exhibits that will leave you and your partner amazed and laughing. It’s an engaging and fun way to connect with your partner and challenge your perceptions. The museum is filled with Instagram-worthy spots, so don’t forget to snap a few memorable photos!
Address: 25 E Washington St, Chicago, IL 60602
18. Interactive Games at Activate
Activate is an interactive gaming experience in Chicago where you and your partner can enjoy a variety of games like digital darts, virtual bowling, and more. This place is perfect for newlyweds who want a blend of technology and fun physical activity. With its high-tech environment and a variety of games to choose from, it’s a great way to bond, compete, and have a blast together.
Address: 3801 N Southport Ave, Chicago, IL 60613
19. Magic Show at The Magic Parlour
For a truly enchanting evening, head to The Magic Parlour for a mesmerizing magic show by the talented magician, Dennis Watkins. Held in an intimate, vintage-style theater, the show is full of mind-boggling illusions, sleight of hand, and audience participation. This unique, intimate experience is perfect for a date night that’s both mysterious and full of wonder.
Address: 10 W Randolph St, Chicago, IL 60601
20. Murder Mystery Dinner with The Murder Mystery Co.
Looking for a fun and interactive way to spend your evening? Host a murder mystery with The Murder Mystery Co. They offer private events where you and your partner, along with friends, can become part of a thrilling murder mystery. It’s a great way to enjoy a night of suspense, teamwork, and lots of laughs while solving a whodunit together.
Address: Various locations throughout Chicago (check their website for booking)
21. Take a Underground Donut Tour
If you're both sweet tooth enthusiasts, the Underground Donut Tour is a must! This walking tour takes you through Chicago’s best donut spots, allowing you to sample a variety of mouthwatering treats while learning about the city’s history. It’s a delicious and quirky way to explore Chicago while indulging in your favorite sweet treats.
Address: 1341 N Milwaukee Ave, Chicago, IL 60622 (starting point)
22. Classic Films at The Music Box Theatre
For a cozy and nostalgic movie night, visit The Music Box Theatre, one of Chicago's oldest and most iconic independent cinemas. This charming venue screens a mix of classic films, indie releases, and special events. With its beautiful vintage décor, the Music Box creates a warm, intimate setting perfect for couples who want to enjoy a good movie together in a historic atmosphere.
Address: 3733 N Southport Ave, Chicago, IL 60613
23. Beautiful Exhibits at The Art Institute of Chicago
If you and your partner enjoy art and culture, a visit to The Art Institute of Chicago is a must. The museum is home to world-renowned exhibits, including iconic pieces from artists like Van Gogh, Monet, and Grant Wood. Wander through its stunning galleries, enjoy the beautiful architecture, and immerse yourselves in the world of art together.
Address: 111 S Michigan Ave, Chicago, IL 60603
24. Visit Escape Game Chicago
For a thrilling and challenging date, head to Escape Game Chicago, where you and your partner can solve puzzles and complete tasks to “escape” within an hour. With various themed rooms to choose from, you’ll need to work together, think critically, and communicate effectively to make it out. It’s an exciting way to bond and test your teamwork skills.
Address: 35 W Grand Ave, Chicago, IL 60654
25. Take a Stroll with Chicago Prohibition Tours
Step back in time and experience the roaring '20s with a Prohibition-era tour. Chicago Prohibition Tours takes you to speakeasies and historical sites where you can learn about the city’s underground drinking culture during Prohibition. Enjoy cocktails and fascinating stories of Chicago's past in a fun, immersive setting.
Address: Various locations throughout Chicago (check their website for details)
26. Stop at Millennium Park
Millennium Park is an iconic Chicago landmark and a great spot for a romantic stroll. You can take in the beautiful landscape, visit the famous Cloud Gate (aka "The Bean"), and enjoy free concerts in the summer. It's an easy and laid-back way to enjoy each other's company while taking in the city's culture and beauty.
Address: 201 E Randolph St, Chicago, IL 60602
27. Skydive at IFLY Indoor Skydiving
For adventurous newlyweds, IFLY Indoor Skydiving offers a thrilling experience that lets you feel the rush of skydiving—without jumping out of an airplane. You’ll be briefed by an instructor and then have the opportunity to “free fall” in a state-of-the-art vertical wind tunnel. It’s an unforgettable experience for couples who crave excitement and adrenaline.
Address: 800 W. Armitage Ave, Chicago, IL 60614
28. Relax at AIRE Ancient Baths
For a more relaxing date night, treat yourselves to the luxurious AIRE Ancient Baths, inspired by the traditional bathhouses of ancient Greece, Rome, and Turkey. Enjoy the thermal baths, massages, and tranquil environment for a truly rejuvenating experience. This is the perfect activity to unwind and connect on a deeper level.
Address: 600 W Chicago Ave, Chicago, IL 60654
29. Take a Cooking Class at The Chopping Block
For food-loving couples, taking a cooking class at The Chopping Block is a fun and educational way to spend your date night. Choose from a variety of classes, ranging from Italian cuisine to baking, and learn how to prepare a delicious meal together. It’s a great way to bond over your shared love of food while picking up new culinary skills.
Address: 4756 N Lincoln Ave, Chicago, IL 60625
30. Ancient History at the Field Museum
Step into a world of ancient history with a visit to the Field Museum. This world-class museum features incredible exhibits, from dinosaur skeletons to ancient Egyptian artifacts. Spend the day exploring the fascinating exhibits and learning about the history of our world, making it a memorable and educational date.
Address: 1400 S Lake Shore Dr, Chicago, IL 60605
31. Pizza at Chicago Pizza and Oven Grinder Company
For a unique and delicious twist on pizza, stop by the Chicago Pizza and Oven Grinder Company. They’re famous for their pizza potpies—an incredibly flavorful deep-dish pizza served in a bowl. The warm, cozy atmosphere makes it a great spot for a romantic and tasty date night.
Address: 2121 N Clark St, Chicago, IL 60614
32. Kayak Rentals at Montrose Beach
For an active and outdoorsy date, rent a kayak at Montrose Beach and paddle along Lake Michigan. The serene water and beautiful skyline views make for a peaceful and scenic date. Whether you’re experienced or new to kayaking, it’s a fun way to enjoy the natural beauty of the city while spending quality time together.
Address: 4400 N Lake Shore Dr, Chicago, IL 60640
33. Take a Ride with the Chicago River Boat Architecture Tours
For a relaxing yet informative date, take a Chicago River Boat Architecture Tour. You and your partner can cruise down the river while learning about the city’s famous architecture from expert guides. The views of the skyline are spectacular, and the tour offers a fascinating look into the design and history of Chicago’s iconic buildings.
Address: 112 E Wacker Dr, Chicago, IL 60601 (departure point)
Conclusion
No matter what kind of date night you're in the mood for, Chicago has a wide array of activities that will create lasting memories for newlyweds. Whether you're exploring new flavors, competing in games, or simply enjoying each other's company in a cozy atmosphere, the Windy City offers something for every couple. From the charming to the quirky, each activity provides a unique opportunity to strengthen your bond and experience Chicago in an exciting way. Let the adventure begin!
About the Author
Sasha is a wedding photographer based in the Chicagoland area, with a passion for capturing the moments that make each couple's story unique. She loves writing blog articles that cover a wide range of topics, from portrait locations to gift ideas, wedding advice, and more—anything that will help her couples create a meaningful and stress-free journey. When she’s not behind the camera, Sasha enjoys traveling internationally and indulging in her favorite treat, salted peanut butter ice cream from Jeni’s. Sasha also spends her downtime hanging out with her foster cat, Missy, and listening to pop punk bands. Currently, she’s booking weddings for 2025 and 2026, and she’s excited to help even more couples bring their wedding visions to life!
