37 Easy and Romantic Ways to Celebrate Valentine’s Day

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Valentine’s Day. It comes around every year but that doesn’t make it any less easy to plan for. Depending on your status, you may choose to celebrate with your partner, friends, or by yourself.

No matter how you choose to celebrate this season of love, we have you covered with plenty of options to make this Valentine’s Day special—from heart-shaped dinners to virtual concerts. Here are some easy and romantic ways to celebrate Valentine’s Day.

Note: Effective January 3, any individual age 5 and older will be required to show proof of vaccination to dine indoors, visit gyms, or enjoy entertainment venues where food or drink is being served. Learn more by visiting Chicago.gov.


Valentine’s Day activities and ideas

1. Spend some time with your ‘girls’ and celebrate Galentine’s Day.

2. Cook dinner together and sample each other’s dishes.

3. Make a playlist with your favorite love songs.

4. Write each other love letters.

5. Try an indoor date idea from this amazing list.

6. Wear something sexy—or nothing at all.

7. Go out to dinner at a fancy restaurant.

8. Take on a couple’s themed Tik Tok challenge.

9. Share your favorite memories over a glass of wine.

10. Surprise them with a staycation in a nearby hotel or resort.

11. Buy them something they would never buy for themselves.

12. Share a slice of heart-shaped pizza from any of these notable restaurants.

13. Watch the planets align and go stargazing.

14. Share a box of sweets from a local confectionary with your sweet.

15. Prepare their favorite dessert.

16. Create a romantic scavenger hunt.

17. Turn up the heat with a competitive game night.

18. Serenade each other with your favorite love songs.

19. Attend a virtual or in-person concert.

20. Master new recipes together from social media.

21. Read your favorite poem or create your own.

22. Take a scenic stroll.

23. Buy them a stunning floral arrangement.

24. Recreate your first date night.

25. Do a craft together.

26. Dance the night or day away.

27. Snuggle up in your favorite PJs all day long.

28. Explore one of these fun winter activities.

29. Order delivery or take out from a new restaurant.

30. Record a loving voice note or video message.

31. Take a virtual mixology class.

32. Grab dinner with a view of the city’s skyline.

33. Pamper one another with a DIY spa day.

34. Arrange a romantic picnic.

35. Have a themed date night.

36. Plan your next getaway.

37. Tell them “I love you.”

These activities are just a few ways to celebrate, check out events happening in Chicago that are also great for celebrating the holiday.

Other events that you are sure to love:

Real Men Love celebrates Black on Black Love: Celebrate Black on Black Love at The Quarry Event Center with a couples dinner and a show.

Valentine’s Winemaking Experience and Dinner: Make taste, explore, and create a wine with your partner.

Wine Lover’s Valentine’s Day at Volo: Enjoy a romantic multi-course prix fixe dinner at one of Chicago’s most notable wine bars.

The Best of Soul: Live Band Tribute: North Bar hosts a Valentine’s Day edition of “The Best of Soul” featuring music from R&B legends performed by Brandon James.

KOVAL Valentine’s Day Weekend Tour: Try something new this Valentine’s Day weekend with a tour of the Koval distillery and spirit samples paired with bite-sized treats and lessons you can use at home.

Valentine’s Market at The Plant: VisitThe Plant in the Back of the Yards neighborhood for Valentine’s market, offering guests a one-of-a-kind selection of small businesses and local vendors.

St. Valentine’s Day Massacre: Explore the historic side of Valentine’s Day with a virtual event detailing the infamous crime.


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