Chicago Valentine's Date That'll Make You Feel The Love

Chicago Valentine's Date That'll Make You Feel The Love

  • 04/17/19

Valentine's Day is just around the corner, and it's time to plan something big for your date night. Wether you're looking for a low-key dinner in the neighborhood or a cross-town trek for a fun activity, there are plenty of options. Get started creating a memorable, entertaining evening with this negihborhood guide.

Have A Great Valentine's Day With These Date Ideas

Image by Payton Chung

Wicker Park/Bucktown

Spend a Night at The Robey

Take in the incredible Chicago skyline from The Robey, a Wicker Park staple located on North Avenue and Milwaukee Avenue. This 203-foot tall art deco building hosts a stunning hotel where you can enjoy one another’s company and the period decor. Choose from the 89 rooms including spacious suites and be sure to stop in for a cocktail at the UP Room between 5 p.m. and 6 p.m. on weeknights to take advantage of the guest-only amenity.

Play Whirlyball

Couples looking for a little friendly competition this Valentine’s Day should go to WhirlyBall to try this fun, innovative game. You’ll hop into bumper cars armed with lacrosse scoops and whiffle balls and try to score on your opponents. The game requires at least four people so show up as a couple and join strangers or make it a double date with some pals. Bowling, laser tag and tasty food and drinks are also available at this entertainment destination.


Nothing say’s Valentine’s Date quite like an evening of Italian cuisine at Antico Chicago. Guests here are treated like family and enjoy the comfortable-yet-upscale atmosphere of the neighborhood restaurant. The chef team values freshness, and it shows in their incredible house-made pasta like gnocchi, tagliatelle bolognese and risotto. Whether you go for the roasted beets and arugula salad with goat cheese and fig vinaigrette or the grilled rib eye with roasted bone marrow be sure to top off the night with fresh seasonal gelato.

Photo from BadAxe Throwing

The Loop/Gold Coast

Try Ax Throwing​​​​​​​

Do you and your partner crave adventure in the city? Stretch your forearms and do some shoulder circles before heading to Bad Axe Throwing to try your hands at the old lumberjack game of ax throwing. Bring non-alcoholic drinks and food and try to best each other by seeing who can hit the bullseye the most. Make a reservation or check out their walk-in hours.

Take a Walking Architectural Tour

Those who enjoy Chicago history and architecture will love taking a walk-through tour of the Charnley-Persky House Museum on Aster Street. A young Frank Lloyd Wright was involved in the creation of the modern home as the junior draftsman to architect Louis Sullivan. Tours are first-come, first-serve at noon on Wednesdays and Saturdays.

Photo by Bang Bang Pie

Logan Square

Learn to Bake at a Pie Class

Take a dessert class from the masters at Bang Bang Pie to learn how to create their delicious apple or key lime pies. The admission cost comes with small bites, one slice per person and the skills to go home and wow your loved ones with your newly acquired baking expertise. Classes are available monthly so check the website for the February option.

Stretch Out at a Couples Yoga Class​​​​​​​

​​​​​​​Take a private couples yoga class at Temple of Kriya Yoga where you’ll learn the asana or physical practice of yoga together. These classes are about learning proper alignment while focusing on the breath and celebrating your bodies. Advanced and beginner yogis will love this customized couples activity! Sign up ahead of time to schedule the private class.

Dig in at Daisies
After partaking in some fun local activities, you’ll need sustenance so head straight to Daisies on Milwaukee Avenue. Chef Joe Frillman runs this family-owned and -operated farm-to-table restaurant that features vegetables straight from the Frillman Farm. The eatery is known for their pasta and seasonal dishes, and offers fresh, flavorful dishes for brunch, dinner and drinks. Start the evening with an herb salad complete with radish and apple before digging into linguini with ramps, pickled pears, bacon and egg yolk. Don’t try to share a house-made root beer and vanilla ice cream float - you’ll need two!

Photo from the Music Box Theatre

Lakeview/Lincoln Park

Catch a Film

If your idea of a great date includes popcorn and a movie go straight to Music Box Theatre for a classic Valentine’s flick. The beautiful old venue shows interesting indie films and award winners like, “The Room,” and “Cold War.” They also feature throwbacks to past favorites like “Rocky Horror Picture Show” so check the calendar to see what films suit your viewing preferences.

Stroll a Plant-filled Glass Dome
​​​​​​​Couples who need a break from the winter chill should visit the Lincoln Park Conservatory to take in the plants and enjoy the warm, humid atmosphere. Make sure to stop by the Orchid House and Fern Room to see unique flora from all over the world. You’ll leave feeling refreshed and ready to explore the rest of beautiful Lakeview.

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