Valentine’s Day Chicago Style

Most bloggers are blogging about Valentine’s Day while all their boyfriends/fiancées/husbands take their photo in a pretty red dress; I, however, am going to give you the other side. In a robe. On a fluffy white bed. About ~*my kind of*~ dating life and then proceed to tell you and your date where to go in the city.

You may be a girl, or a boy reading this who are in the “in-between stages” of dating. I don’t even know what that means, (Because we are Millennialsheyyyy!) but, hopefully, you understand? Like, you’re dating, but don’t really know what’s really going on? Having fun, but then Valentine’s Day pops up and you’re kind of like that meme of Homer Simpson (I’ve never watched the Simpsons, but think it’s hilarious) backing up into the bushes…like ehhh…. I’ll talk to you Sunday… nobody talks Monday, Tuesday then one of you send the “What’s Up” text maybe Wednesday night.

Don’t get me wrong, I love Valentine’s Day. Love is in the air, chocolate is everywhere and everything is pink. It’s just that I have never really celebrated it. Let me guess… you’re thinking,

“Well, yes you have, Ally. Elementary school and middle school were prime years to swap those cheesy Valentine’s Day cards with your friends and crushes.”

You would be correct, except I was the little girl out sick EVERY VALENTINE’S DAY with strep throat. So, no Valentine’s for moiBut that’s not even the point. My point here is to help you with your Valentine’s Day, so see my options below: 

Dreaming of Breakfast in bed for Valentine’s Day <3


Where to take your ~*kind of date*~ on Valentine’s Day in Chicago

The Boujee People:

  1. Nellcote 
    1. I love this French inspired restaurant. If you are looking for something a bit more intimate you can also head over to Maude’s Liquor Bar right down the street.
  2. Valentine’s Day Whiskey and Oyster Pairing
    1. A pop-up exclusively for Valentines Day!
  3. The Violet Hour
    1. Dark high back chairs and candlelight with incredible cocktails.

The Hands-On People (via Modern Luxury):

  1.  Chopping Block
    Take the usual dinner date a step further at the Hands-On Valentine’s Feast, where you and your Valentine will learn to cook an eight-course meal together.
  2. Brooklyn Boulders
    Climbing is a one-of-a-kind way to take your relationship to new heights. Drop by or sign up for a class and learn how to climb, boulder and belay with your special someone.
  3.  Penguin Foot Pottery
    Get your hands dirty and leave with a fun unique, hand-crafted gift for your Valentine.

The Funny People:

  1. The Valentine’s Day Undie Run
    1. If you love spending the day in nothing but your underwear, this is the day… note: must be a runner
  2. Festival of Laughs
    1. Laugh all you want at the Festival of Laughs, or check out Laugh Factory or Second City!



  1. Caudalie – Can be bought at Sephora. It is french, amazing and is a wonderful gift
  2. Chanel Lipstick – Can be bought on Michigan Ave or State Street in Macy’s
  3. Exhale Spa gift card – facial, massage, both? Win, win either way!
Valentine’s Day gift post is going live on the blog this weekend. ♥️ Here’s a sneak peek of a few of my favorite for-her gifts. #ValentinesDay #igerschicago
Off Duty #windycityblogger #igerschicago

















  • Reply Taylor Meehan February 22, 2017 at 10:50 AM

    I try to take my boujee friends to Soho House 🙂 Thanks for the recommendations!

    • Reply Ally February 22, 2017 at 11:59 AM

      That’s a good one too!!

    Leave a Reply

    This site uses Akismet to reduce spam. Learn how your comment data is processed.