10 Romantic Date Night Ideas in Chicago


The dating scene in Chicago just became more interesting with these 10 romantic date night ideas. From watching a Drunk Shakespeare play to taking a helicopter tour, there’s something for every couple looking to spice things up in the Windy City. And hey, why not embark on a brewery or distillery crawl while supporting local businesses? Or explore the rich cultural heritage of Chicago by visiting one of its world-class museums. And who could resist the thrill of getting high above the city and watching a sunrise from the beach? Get ready to create unforgettable memories with your loved one in the most happening city of Chicago.

1. Watch a Drunk Shakespeare Play

Looking for a unique and unforgettable date night idea in Chicago? How about watching a Drunk Shakespeare Play? It’s a one-of-a-kind experience where actors attempt to perform a Shakespearean play after downing shots of various alcohols. With each show being different depending on who’s drinking and what they’re drinking, you’re in for a hilarious and unpredictable evening. Just make sure you’re 21+ with a valid ID. So grab your date, head to The Lounge At The Lion on North Wabash Avenue, and get ready to laugh your socks off! Tickets start at just $29 per person. Cheers to Shakespearean revelry! Let’s move on to more exciting date night ideas in the Windy City!

2. See a Magic Show

Chicago is a city that knows how to entertain, and when it comes to romantic date night ideas, the Windy City truly delivers. Whether you’re looking for a night filled with laughter, magic, or breathtaking views, Chicago has it all. So, let’s dive into some of the best date night activities the city has to offer. 2. **See a Magic Show** Step into the world of illusion and wonder by taking your date to a magic show. Chicago Magic Lounge, Trickery Chicago Magic Show, and Dennis Watkins’ The Magic Parlour are all top-notch options that will leave you both amazed and entertained. Prepare to be dazzled by mind-bending tricks and mindblowing illusions as you and your date are transported to a world of mystery and enchantment. Get ready for an evening of wonder and awe that will leave you both spellbound.

3. Laugh at a Comedy Show

Want to have a date filled with laughter? Take your significant other to one of Chicago’s hilarious comedy clubs. Second City is famous for producing comedy legends like Tina Fey and Bill Murray. iO Chicago and Laugh Factory Chicago are also great options. Nothing bonds couples better than sharing a good laugh, and with these comedy clubs, you’ll be in for a night of jokes and giggles. So, gear up for a hilarious evening and get ready to laugh your socks off! Just make sure that your date doesn’t laugh so hard they fall off their chair. Safety first, people!

4. Join a Fireworks Cruise

Join a Fireworks Cruise Experience the magic of fireworks on a romantic cruise! Take your date on a Wednesday or Saturday night in the summer and embark on a journey across the water to witness an awe-inspiring display of lights. Whether you choose a lake or river cruise, the spectacular views and the sparkling night sky will surely set the mood for a romantic evening. So sit back, relax, and enjoy the dazzling fireworks as you and your partner create unforgettable memories together. It’s the perfect way to add some sparkle to your date night!

5. Take a Helicopter Tour

3. Laugh at a Comedy Show: If laughter is the way to your heart, head over to Second City for a night of laughter. With famous alums like Tina Fey and Bill Murray, this comedy club guarantees an evening of non-stop chuckles. Other great options include iO Chicago and Laugh Factory Chicago.

If you want to elevate your date to new heights, a helicopter tour is the way to go. The ultimate thrill for any couple, soar above the city and enjoy breathtaking views. It’s a splurge, but the experience is worth every penny.

6. Relax in Thermal Baths at AIRE Ancient Baths

Relax in Thermal Baths at AIRE Ancient Baths: Let’s take a break from all the action and indulge in some much-needed relaxation at AIRE Ancient Baths. Picture this: you and your partner luxuriating in thermal baths, getting soothing massages, and experiencing exclusive rituals. Ahh, the bliss! AIRE Ancient Baths Chicago offers a tranquil and serene atmosphere where you can unwind after a day of exploring the city. Let the healing waters rejuvenate your body and soul as you create unforgettable memories with your loved one. Plus, who doesn’t love a little pampering? Take a deep breath, let go of all your worries, and dive into the ultimate relaxation experience at AIRE Ancient Baths. After all, you both deserve it.

7. Embark on a Brewery (Or Distillery) Crawl

Embrace your inner beer connoisseur and explore the hoppy delights of Chicago with a Brewery (Or Distillery) Crawl. With a plethora of options, you and your date can craft your own unique tasting experience while supporting local businesses. Sip on a variety of craft beers or sample some locally distilled spirits as you dive into the city’s vibrant brewing scene. It’s a win-win situation – you get to tantalize your taste buds and contribute to the local economy. Plus, who doesn’t love a date that revolves around good drinks? Cheers to that!

8. Take Advantage of Chicago’s Many Museums

Chicago is not only famous for its deep-dish pizza and windy weather but also for its incredible museums. If you and your partner are looking for a cultural conversation on your date night, then Chicago’s many museums are perfect for you. From art to zoology, natural history to science, and local history, Chicago is home to dozens of world-class museums that will leave you in awe. One option is the Art Institute of Chicago, which houses a vast collection of masterpieces from around the world. You can wander through the halls, hand in hand, appreciating the beauty of Van Gogh’s “The Bedroom” or Monet’s “Water Lilies.” Another option is the Museum of Science and Industry, where you can explore interactive exhibits, learn about space and technology, and even walk through a German U-boat from World War II. For a unique experience, visit the Field Museum, where you can come face-to-face with Sue, the largest and most complete Tyrannosaurus Rex skeleton ever discovered, or delve into the mysteries of ancient Egypt. No matter what your interests are, Chicago’s museums offer something for everyone. Plus, visiting these museums will not only provide you with a fascinating date night but also support local Chicago businesses. So, why not add a cultural twist to your romantic evening and explore the wonders of Chicago’s museums together?

9. Get High (Above The City)

As we reach the ninth spot on our list, it’s time to take your date to new heights..literally! Get ready to soar above the city and experience the breathtaking views of Chicago. Take them for dinner or drinks at The Signature Room on the 95th floor of 875 N. Michigan, or head to 360 Chicago on the floor below for panoramic views and a chance to test their thrill tolerance on Tilt! And let’s not forget about the Willis Tower’s Skydeck, where you can enjoy thrills and cute photo opportunities. So, buckle up and get ready for a sky-high date night in the Windy City!

10. Watch A Sunrise From The Beach

Nothing screams romance like watching a beautiful sunrise with your loved one. Head to one of Chicago’s stunning beaches early in the morning and witness nature’s breathtaking display of colors as the sun rises above Lake Michigan. The calm and serene ambiance, coupled with the gentle sound of waves crashing, will create a truly romantic and unforgettable experience. Don’t forget to bring a cozy blanket and some warm beverages to make the moment even more special.


Chicago is a city full of excitement and fun, which makes it the perfect place for a romantic date night. From Shakespeare plays to magic shows, comedy clubs to fireworks cruises, there are plenty of unique and enjoyable activities to do with your partner. Indulge in a relaxing thermal bath experience, embark on a brewery or distillery crawl to support local businesses, or explore the city’s world-class museums for a cultural conversation. For breathtaking views, take a helicopter tour or watch a sunrise from the beach. The possibilities are endless in Chicago! So, why settle for a typical dinner and a movie when you can create unforgettable memories in this vibrant city? Get ready for an extraordinary date night that will leave you wanting more.

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