Our list of the 20 best Valentine's Day activities in Chicago, Illinois

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Looking for a good time on Valentine’s Day in Chicago, Illinois?

There are a lot of great events on or around Valentine’s Day in Chicagoland that are perfect for this holiday.

These events are great whether you want to share it with your love, share it with the friends you love, or share it with others looking for love.

So here at Green Vacation Deals, we came up with our list of the 20 best.  But please be warned – a lot of these activities are selling out fast.  So book your tickets ASAP!

    1. Candlelight: Valentine’s Day Special
    2. Love Struck – AirOtic Soirée
    3. One Direction Dance Party x Valentine’s Day with DJ Kenny Braasch & DJ Real Co
    4. Valentine’s Soul Jam
    5. Heart of Chicago Soul Club — Valentine’s Day Dance Party
    6. Valentine’s Day Comedy Show
    7. Valentine’s Romance with Susanne Hou
    8. Dinner Cruise
    9. Valentine’s Day with Ella & Louis
    10. Chicago Party Clowns – My Funny Valentine
    11. Chicago Romantic Date Private Art Experience
    12. Couples Massage at Allure De Vie Salon and Day Spa
    13. Private Dance Lesson for Couple at Sterba’s DanceSport
    14. Chicago Romantic Date Night Pottery Class
    15. Anti-Valentines Day Valentines Day Crawl
    16. Valentine’s Day Cupid’s Ball
    17. Valentine’s Day Festa
    18. Galentine’s Craft Night at Federales in Fulton Market / West Loop
    19. Salsa for Singles – Valentine’s Day Edition
    20. Poetry, Paint and Vibe – Single Ladies Valentines Day

Valentine's Day in Chicago 2026 Guide