Romantic Date Night Activities in Chicago

Photos By: Paige Medor in Collaboration with ModCloth

red heart Modcloth Dress

Valentine’s Day has never really been my favorite holiday. Sometimes it feels a little forced to dedicate a day to love. I also think it’s quite commercial and materialistic feeling like you have to buy this elaborate gift for someone right after the holidays. But as I’ve gotten older I have become more aware of the importance to spend quality time with your partner and show them how much they mean to you. That’s why I love doing experiences together rather than giving physical gifts. Below are a few romantic spots to take your honey for the holiday or if you’re like me the day after.

Art Institute of Chicago

I think I’ve said this before but one of my favorite places in the city is the Art Insitute a quiet weekday wandering the halls of beautiful art. My favorite wing is the Modern Art Wing and the Photography exhibits. It’s a great way to have some really great conversations with your significant other and learn how creative they think.

Comedy Club

If you like stand up Chicago’s comedy clubs like Zanies, Second City and Laugh Factory are the perfect place for you and your lover to laugh it up.  Chicago is where so many incredible comedians got their start, you never know your Valentine’s Day date might be the way you discover the countries next top comedian.

Jazz Night at the Green Mill

Chicago’s music scene is one of the best and has so much history. Mike and I love to spend a quiet evening sipping cocktails and listening to jazz at the classic Green Mill in Uptown. Take a step back in time into Al Capone’s well preserved iconic bar.

Adler Planetarium

What’s more romantic than learning about the vast unknown. I love looking at the stars and learning about space. Walkthrough time and space or take a look at Chicago’s night sky together. 

Downtown Staycation at The Langham Chicago

Valentine’s Day is on a Friday this year, so make it a weekend of romance at the Langham Chicago. This luxurious hotel on the Mag Mile has a beautiful view of the city and is conveniently located if you are looking to take in more of the city. But the indoor pool, luxury spa and dining options inside the hotel are also a great way to spend some alone time. 

Drinks at Dorian’s

This is a place I recently discovered and I think it’s the perfect spot for any audiophiles. This record store has a secret tiki-style cocktail lounge in the back. Peruse the records and then take your treasures to the back for a quick drink.

Dinner in Fulton Market

Fulton Market is Chicago’s hottest food district there are so many incredible restaurant concepts in this area. Including my favorite veggie-forward restaurant and bar. With seasonal small plates menu and cocktails to accompany them this beautiful restaurant is a great place to try some delicious veggie dishes. If that’s not your cup of tea this neighborhood is teaming with delicious dining options. 

Aire Ancient Baths Chicago

If you and your bau need a little R&R check out the Aire Ancient Baths. Explore their thermal bath options, couple’s packages and even massage options for a day of pampering.  

Looking to explore the universe, take a step into the art world, laugh at a comedy show, check out some live music or sip craft cocktail. Or maybe spend your Valentine’s Day pampering yourselves the most important part of the holiday is to show your special someone they’re loved. How are you spending Valentine’s Day?


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