Romantic Valentine’s Day Date Ideas

The thing that I love most about Valentine’s Day is that it helps my husband and I reconnect. After the hustle and bustle of the holidays and the winter doldrums of January, we tend to simply be ships passing in the night. So when February rolls around, we snatch up a sitter and plan a fun date for us to be able to really enjoy each other’s company sans kids. I mean, when was the last time you and your partner had MEANINGFUL time together that didn’t involve goldfish crackers and sports practice? Change all of that by taking your valentine out for one of these romantic dates in Chicagoland.

Valentine’s Dinner at the Brookfield Zoo

February 9

Tickets: $230/ticket

This adventurous dinner date begins with a cocktail reception amidst the giraffes at Habitat Africa and continues to a romantic four-course meal featuring filet mignon and lobster at Bocaditos. Includes full bar service and musical entertainment for a night to remember.

Chicago Philharmonic at City Winery Sunday Brunch

February 17

Tickets: $25 General Admission ticket, plus $20 brunch buffet option

The Chicago Philharmonic’s string fab four will share their interpretation of beloved Beatles songs while you and your valentine enjoy a delicious brunch buffet from City Winery.

Joffrey Ballet’s World Premiere of Anna Karenina

February 13-24

Tickets: $35-$199

Choreographer Yuri Passokov brings Leo Tolstoy’s epic 19th-century story of passion and forbidden love to the Auditorium Theatre. It is a first-time collaboration between the Joffrey Ballet and the renowned Australian Ballet, a perfect way for couples to enjoy a romantic ballet performance.

La traviata at the Lyric Opera House

February 16-March 22

Tickets: $99-$299

Sung in Italian with projected English translations, the music in La traviata is incomparable, with one beautiful melody after another. In his Lyric debut, Michael Christie will conduct a star-studded cast that tells the story of one of opera’s most glorious heroines.  

And if you are looking for a more traditional date, be sure to check out my favorite romantic restaurants in Chicagoland.

Happy Valentine’s Day!


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  1. Christa says

    Ugh, a night at the opera is my idea of heaven and my husband’s idea of hell. Lol. The zoo would be an enjoyable compromise.

    • Amanda says

      Agreed! I’m really hoping we can make it to the City Winery event. It would be so nice to connect, just the two of us, over good food and with good music.

  2. Tami says

    While my husband would probably enjoy the opera, I’m game for Valentine’s dinner at the Brookfield Zoo. We will have to see who gets their way this holiday.

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