Trendsetter Thursday

Although Valentine’s Day seems to be a “Hallmark” holiday, I think it’s important for everyone to embrace it. Whether you’re in a relationship or celebrating it with your gals, it’s always nice to build a stronger connection with them. So why not use this day to dress up, or dress down, to celebrate it with the ones you love. From restaurants to theaters to bars, here’s my top ten places to go, in Chicago, for the perfect Valentine’s Day date.

1. Headquarters Beercade:

  • Not only can you reminisce your childhood but you can drink to it too! This is the perfect spot for a casual and fun date. Plus, you can always make a friendly bet to see who still has “game” 😉 Check either one of the locations here.

2. Ballroom Dance Chicago:

  • Spice things up with your date through the rhythm of Rumba and Salsa *insert dancing lady emoji here haha*. Yes that’s right, you and your partner can dance the night away with couples dance classes. Not only will you learn a thing or two about these sexy dances but you will also be provided with hors d’oeuvres and sparkling wine. Hello! Purchase your tickets for either Saturday and/or Sunday before it’s too late.

3. Lyric Opera House:

  • Skip the average date and spend the night before Valentine’s Day at the Lyric Opera House. This is the perfect excuse to dress up and live the glamorous night out. Click here for tickets. PS: Romeo & Juliet will be available after Valentine’s Day in case you wanted to extend more dates with your Valentine 😉

4. Geja’s:

  • Two words: fondue dining! Go ahead, drool now haha. Visit their site to make reservations.

5. Piccolo Sogno:

  • How would you like to spend the night in Italy without actually spending all of that money? That’s what Piccolo Sogno does with its authentic Italian food. This restaurant is rated as one of the best ones in Chicago for its food and atmosphere. They will be offering aphrodisiac inspired specials to go along with the regular menu. Plus, all you beautiful ladies will get a rose for dining with them! It would be the most romantic way to spend Valentine’s Day. For reservations, visit their site or call 312-421-0077.

6. Margie’s Fine Candies:

  • A blast from the past; the setting of this ice cream parlor will make you believe as if you were back in time. “Musical legends, Hollywood greats and sports stars — and even famous gangster Al Capone — have found sweet release at Margie’s Candies.” Their ice cream and decor will make you want to come back for more. FYI: They do offer regular food as well, which is delicious! Don’t believe me? Check it out for yourself here.

7. Pickwick Theatre:

  • Want to spend Valentine’s Day more cozy but still go out? Pickwick Theatre in Park Ridge is the perfect spot for that. This is another gem that has been up since the 1920’s! Think of it like an Allie and Noah date. For showtimes, visit all of their information here.

8. The Four Treys Tavern:

  • If you want to spend Valentine’s Day with your friends AND dog then by all means go for it and look no further! This bar is dog friendly. Yes, mhm, you read that right. You can bring your furry little friend and drink a beer too. I wouldn’t recommend getting drunk while you’re with your dog however. Personally, I haven’t brought my Chiquilin in there because I always get carried away with the karaoke haha. Check out their specials here.

9. The Chopping Block:

  • They say that the way to anyone’s heart is through food. Heck I cannot argue with that haha. Win your sweetie’s heart by taking a cooking class together at The Chopping Block.

10. Home:

  • Build a fort and order food with your loved one. Turn off your phones and truly enjoy quality time together; nothing is more valuable than that.

What are some of your favorite spots to spend Valentine’s Day?

Valentines Day OOTD
Valentines Day OOTD
Valentines Day OOTD
Valentines Day OOTD

Yours truly,


Photographer: Anthonie Arboleda