Unique Date Ideas in Chicago: 10 Hidden Gems

Couples Adventures
Mar 3
2 min read

Chicago is a bustling city filled with iconic date spots, but if you're looking for something unique and off the beaten path, you've come to the right place! Whether you're a local or visiting, these 10 hidden gem date ideas will make for an unforgettable experience in the Windy City.

1. Explore the Secret Speakeasies

Step back in time with a romantic night at one of Chicago's hidden speakeasies. Bars like The Violet Hour and The Drifter offer craft cocktails in an intimate setting, making your date experience unforgettable.

2. Take a Kayak Tour on the Chicago River

If you and your sweetheart aim for a more adventurous, outdoorsy date, paddle through the city's heart with a guided kayak tour. Companies like Urban Kayaks offer twilight tours with stunning skyline views.

3. Visit the Garfield Park Conservatory at Night

Escape the city bustle and wander through lush greenery at the Garfield Park Conservatory. Their special evening events create a magical atmosphere perfect for a romantic stroll.

*Garfield Park Conservatory During the Evening*

4. Have a DIY Picnic at Promontory Point

Mix classic and unique by packing a picnic and heading to Promontory Point for breathtaking views of Lake Michigan and the Chicago skyline. It’s a quiet, scenic spot ideal for a relaxing date.

5. Solve Puzzles in an Escape Room

Challenge your teamwork skills by solving clues together in an escape room. The Escape Game Chicago offers unique themes that make for an exciting and interactive date.

6. Take a Glassblowing Class

Try something hands-on and creative with a glassblowing workshop at Ignite Glass Studios. You'll get to make your own art while enjoying a memorable experience

7. Experience a Secret Supper Club

For a dining experience like no other, book a meal at a secret supper club like Dinner Lab or The Underground Supper Club, where menus and locations are a surprise.

8. Watch a Classic Movie at the Music Box Theatre

Enjoy an old-school movie date at the historic Music Box Theatre. Their midnight screenings and indie films make for a cozy and unique outing.

9. Go Indoor Rock Climbing Together

Try indoor rock climbing at Brooklyn Boulders or First Ascent for an active date. It’s a fun way to bond while challenging each other to new heights.

10. Take a Couples’ Dance Class

Learn a new skill and get close with a dance class at Arthur Murray Dance Centers. Whether it's salsa, swing, or ballroom, it's a great way to connect and have fun.