Chicago Date Night Ideas

Whether you’re in Chicago for a special occasion or just looking for something fun to do together, there are plenty of great date night ideas. From romantic restaurants to unique experiences, here are 20 creative Chicago date night ideas to make your evening special.

1. Enjoy a movie screening under the stars at the Chicago Drive-In Movie Series at the historic Portage Park.

2. Take in stunning views of the city from a dazzling rooftop bar like Cindy’s at the Chicago Athletic Association Hotel.

3. Enjoy a romantic boat tour along the Chicago River for a memorable date.

4. Spend an evening together at Chicago’s historic jazz clubs, like The Green Mill and Kingston Mines.

5. Attend an improv comedy show at Second City.

6. Rent a kayak or paddleboard to explore the lakefront.

7. Watch a classic movie at the Music Box Theatre.

8. Take a Chicago Architecture Foundation River Cruise and learn the city’s unique history.

9. Spend an evening supporting local artists at the Chicago Cultural Center.

10. Stroll along the banks of the Chicago Riverwalk and take in the sights.

11. Roast s’mores together at Chicago’s Navy Pier’s outdoor fireplaces.

12. Get lost in the magical Adventure Rooms located all over the city.

13. Share a bottle of wine in a romantic wine garden, like La Sirena Clandestina.

14. Check out the spectacular gardens at the Garfield Park Conservatory.

15. Take in a show at Chicago’s renowned theater district.

16. Go to a rooftop yoga class together and take in the skyline.

17. Taste your way through some of the best food in the city at the Taste of Chicago.

18. Take a romantic, horse-drawn carriage through Lincoln Park.

19. Catch a Chicago Cubs or White Sox baseball game at Wrigley Field or US Cellular Field.

20. Enjoy a picnic together in Millennium Park.