Valentine’s Day Date Ideas in Chicago

Making plans for Valentine’s Day plans can be quite intimidating so we’ve come up with some weekend plans for almost any situation.

For everyone:

No matter where you are on the spectrum of love, Valentine’s Day is the perfect day to show someone you care. Be it your one true love, your best friend, or your mother, show some love this weekend with a beautiful bouquet.

We recommend Flowers for Dreams , a local florist that donates a portion of their proceeds to a local charity. These flowers not only look great, but you’ll feel great too!


For those madly in love:

Begin the evening at Ignite Glass’s Date Night Class! Couples will work alongside one of Ignite’s artists to collaborate in creating a single glass heart of their own design. How cute is that? Also, couples are encouraged to come early or stay late to socialize with other couples while enjoying complimentary sparkling wine and chocolates. That’s right, free bubbly and you might finally find the elusive “couple friends.”Date-Night-Image1 copy

For New Love:

Valentine’s Day can put a lot of pressure on new love, so we’re here to help you keep it casual. Under the Gun Theatre is excited to bring you a night of their most romantic shows. From a reading of “A Match Made on Main Street” to an improvised parody of The Bachelor, you and your honey will be too busy laughing to worry about who is going to drop the “L-bomb” first.

For the Foodie:

If you’re a die-hard foodie but are looking for something a little different this Valentine’s Day, look no further than a date night cooking class at The Chopping Block. With multiple locations throughout the city, there are also numerous classes available. For example, “Date Night” class on February 11th, “Breakfast in Bed” class on February 13th, “Death by Chocolate” class on February 14th. Yum!


For Your Galentine:

Grab your fellow gal-pal and head on over to Stage 773 for the longest running musical comedy in Chicago, Cupid Has a Heart On. This fast paced musical sketch show has been labeled “hilarious, irreverent and a raunchy good time.”


For Young Love:

Valentine’s Day isn’t just for the adults! Share a special night with you little one at one of the many Chicago Park District Valentine’s Day events going on this week. Let your chid(ren) boogie out their energy at one of these Valentine’s Day Dances!


Written by @properties
@properties Christie’s International Real Estate is Chicagoland’s #1 brokerage. Through our affiliation with Christie’s International Real Estate, our network spans nearly 50 countries. No matter your real estate needs, we’ve got you covered.