The Spy and the Submissive

Experience an intense, mysterious scenario with your partner with a Spy and Interrogation theme roleplay. This is particularly perfect for partners who enjoy submissive roles, as it allows an exploration of psychological dynamics within the safety of mutual consent and trust.

Relaxed Creative Retreat

Show off your creative sides by trying out rug tufting and painting activities, followed by a tour of some culinary gems around Chicago. Wrap up this fun-filled date with your favorite movie or show.

Indoor Art Class Date

Get those creative juices flowing as you and your partner join a local art class. No artistic skills are required, just the willingness to try something new.

Chicago Jazz on the Beach

Spend an unforgettable evening with your loved one on Chicago's sandy shores, enveloped by the sweet melodies of live jazz. With a delicious picnic hamper and a stunning view of the city's twinkling skyline as your backdrop, the stage is set for a perfect romantic getaway!

Pizza-Making Date at Home

Why go out for pizza when you can make your own? This date idea allows you to test your culinary skills and bond over something fun. You and your partner can make a night out of it by making your pizza from scratch, including the dough and sauce. Set up a pizza bar with all your favourite toppings, open a bottle of wine and get creative in the kitchen.

Hidden Jazz Club Experience

A perfect surprise for your partner would be a visit to a hidden jazz club in Chicago, Illinois. These hidden gems prove to be some of the most intimate venues in the city, with captivating live jazz music in a secluded yet romantic setting. This offbeat date provides an opportunity to experience another level of the city's culture that many do not know about. It combines music, romance, and a sense of uncovering a hidden wonder.

Surprise Beach Party Date in Chicago

Rekindle the spark with this unique, low-budget surprise date idea. You and your partner can enjoy an evening on one of the several picturesque beaches of Chicago with your very own beach party. It's all about the good vibes, the sound of the beach waves, and the beautiful city skyline in the backdrop. Pack some snacks, light up a portable bonfire, and get ready to dance under the stars.

Looking for more ideas?

Try our AI-powered Date Idea Generator for unique and unforgettable experiences!

Create Your Unique Date

Subscribe to new date ideas