Valentine's Day Date Ideas in Chicago

Updated June 19, 2017

Valentine's Day is the perfect time to spice up date night by trying something new. From burlesque to mixology classes, we've compiled some of our favorites here. For the foodies out there, Ada Street is hosting an alternative version of 'breakfast in bed,' a prix fixe Valentine's Day dinner featuring tasty breakfast foods. Harness your appetite for action with these opportunities to Drink and Do cool stuff for Valentine's!

Planning a night with the ladies?  Read our Galentine's Day Guide.

Celebrate Bromance at Galerie F

Galerie F is Chicago's first art gallery featuring street art, prints, and silkscreen posters. This Logan Square gallery is open to the public 6 days a week, and will be starting a new Bromance exhibit with pieces going on sale online February 15th. Preview the works at the free, family-friendly exhibit opening, from 6-10pm February 10th, sponsored by 21st Amendment Brewery and Essentia Water. Find more art galleries, bars and cafes featuring local art here.

Learn How to Make Your Own Bitters

bitters making class

Hollow Leg will be teaching guests about the history of bitters, how they are used in cocktails, and how to make your own blends of herbs, spices and fruit. This hands-on cocktail class is one of many cocktail courses at this Ukranian Village school of booze. Read more about mixology, cocktail and BYOB cooking classes in Chicago here.

Watch a Game of Thrones-Themed Burlesque Show

Gorilla Tango Theatre has a rotating selection of entertaining productions by local artists and performers. Among them is the Game of Thongs burlesque show, which is the perfect mixture of drama, comedy, and pasties. Find more diva and burlesque shows here

Play Risqué Bingo for a Cause

Hamburger Mary's in Andersonville hosts weekly HamBingo nights to support local charities, hosted by its sassy Diva Velocity Metropolis. For $15, guests have 10 rounds to collect as many prizes as possible. Find bingo nights on any day of the week here.

Shop at Dose Market

chicago dose market

Dose Market is a quarterly pop-up market (typically in West Loop) featuring unique, creative, handmade goods. Dose Market integrates art, fashion, textiles and home goods with food and beverage vendors for a fun day of interactive shopping. Pictured above, one of the interactive elements of Dose Market is the ability to have a poem created for you on the spot and punched out on a typewriter. If that's not #Romance what is? The Love Dose is Sunday, February 12th at Morgan MFG. Find more places to shop and drink here.

Ice Skating and Hot Totties at the Zoo

The Lincoln Park Zoo's seasonal ice skating rink is open nightly until 8pm in February. Grab a hot chocolate or hot tottie in the farmhouse and rent skates for $5. Find other skating rinks and winter activities in Chicago here. 

Watch Casablanca at Music Box

casablanca screening chicago

Music Box Theatre in Lake View will be screening this classic romance film on Sunday, February 12th at 2pm. Music Box is the best place to catch independent, foreign, cult and classic films in Chicago and has a full bar and snacks for you to enjoy at the same time. Find more boozy movie theaters in Chicago here.

Need more date night inspiration? 

Take a Dance Class

Listen to Live Music by Local Artists

Find a Drink and Draw Night for Some Adult Coloring

Play Board Games at a Bar, Brewery or Restaurant

Bring Your Own Food, Kid, and/or Dog to a Brewery

For those recently ending a relationship, perhaps you prefer to throw darts at a picture of your ex - a group activity happening at Diag in Lake View on Saturday, February 11th.