If you click on the links in this post, we may earn money from the companies mentioned in this post, at no extra cost to you. You can read the full disclaimer here.
Looking for a good time on Valentine’s Day in Chicago, Illinois? There are a lot of great things to do around Chicago for those wanting to share it with their love, the friends they love and those wanting to look for love. Here at Green Vacation Deals, we’ve found the 20 best:
- Stupid Cupid Valentine’s Day Crawl
- My Funny Valentine: Valentine’s Day Comedy Show
- Teenage Bottlerocket Valentines Day Special
- Valentine’s Family Fun with Miss Jamie
- Candlelight: Valentine’s Day Special featuring “Romeo and Juliet” and More
- Valentine’s Day Date Night at Q Bar Darien!
- Cupid’s Wine Fest at Hubbard Inn – River North Wine Tasting
- Valentine’s Soul Jam
- Love on the Brain – A Sexy, Valentine’s Themed Floorwork Workshop
- Valentine’s Day-Date Night-Comedy Jam
- “Love is in the Windy City” Chicago Walking Tour
- Valentine’s Day Murder Mystery Dinner and Show
- Mystery Picnic Date: Self-Guided Foodie Adventure
- Private Photo Session with a Local Photographer in Chicago
- R&B Nights: Love Games Live!
- Couples Massage at Allure De Vie Salon and Day Spa
- Love Me Tinder
- Candlelight: Romantic Jazz featuring Billie Holiday, Frank Sinatra, & Ella Fitzgerald
- Private Dance Lesson for Couple at Sterba’s DanceSport
- Men Are From Mars, Women Are From Venus – Live!
