Valentine’s Day ideas: activities throughout Chicago

dance lessons in Chicago
A couple learns to tango.
(photo by Dance Spa)

Guys, there’s less than a week remaining til Valentine’s Day. Hopefully you’ve already made dinner reservations, or have plans to cook a knock-her-tights-off meal at home. (If you’ve slacked, consult this list put together by LoganSquarist.) Either way, you’ll want an activity before or after dinner to make a night of it. I’ve put together a few ideas of things to do in Logan Square, Wicker Park and Bucktown, as well as downtown.

Wicker Park, Logan Square and Bucktown

  • Tango lessons: Take an hourlong lesson with Dance SPA in Bucktown (rated four stars on Yelp) beginning at 7 p.m. Afterward, toast Champagne with your fellow classmates. Register here.
  • Handlebar’s 10th anniversary party: Celebrate everyone’s favorite vegetarian restaurant and bar with live music, including Frank Sinatra ska covers, at Empty Bottle. Entry is free with RSVP.
  • Star Wars-themed burlesque show at Gorilla Tango: For an alternatively entertaining show, indulge in a production whose CTA ads, you must admit, have piqued your curiosity. Show starts at 9 p.m., and tickets are available here. Chicago Reader calls the show “more suggestive than raunchy.”
  • Blues Jam at Rosa’s: Listen to live jazz music at this historic, cozy blues joint that calls itself the friendliest in the city. Show begins at 9:30 p.m.; cover is $7. More info here.
  • Anti-Valentine’s Party at Logan Square Auditorium: Even as one of a twosome, this hilariously salty event sounds like a ton of fun. The event put on by the Chicago Reader starts at 8 p.m., and features locals’ horribly bad date stories, live music by Hood Internet and SloMo, and hosted bar by Budweiser Black Crown til 9 p.m. Tickets are $14 if you buy their Reader deal; $28 per person at the door.

Downtown Chicago

  • Chicago Theatre Week: Running Feb. 12-17, 75 productions throughout the city are performing at discounted rates. Venues include the Goodman Theatre, the Apollo and Joffrey Ballet. View the Feb. 14 schedule here and buy tickets online. Chicago Magazine reviewed a few select shows.
  • Chicago Wolves game vs. Charlotte Checkers: For a sports-themed night or for couples with small kids they can’t seem to displace for an evening, a Wolves game is a fun alternative. Tickets are available online here.
  • DanceWorks Chicago show: For a lunchtime Valentine’s date, head to The Harris Theater for Music and Dance at Millennium Park at noon for romance-themed performances. Food trucks will be parked nearby for some eclectic lunch options. Show tickets are $5, available online or at the theater.
  • Four Girls (And a Guy) Up Comedy Club show: A “cabaret of improvisation, musical numbers and Second City’s signature sketch comedy” is this hilarious sounding love-themed performance. The 90-minute production begins at 7:15 p.m. and costs $28 per person.
  • Ice skating: There are options besides Millennium Park, which undoubtedly will be packed to the brim with tantalized teens on the 14th. Check out the park district’s list of other places to skate throughout the city.

2 thoughts on “Valentine’s Day ideas: activities throughout Chicago

    1. Thanks for the compliment Andrey, and thanks for pointing me to that awesome post by Chicago Detours! I’ll be tweeting about that a little later today. : )

      Happy early Valentine’s.

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