Romantic Date Ideas in Chicago

Yay!  It’s almost Valentine’s Day!  My love for Valentine’s Day started when I was a little girl.  My dad would do the sweetest things for my mom, sister and me.  On Valentine’s Day morning, my dad would wake us up and give us the sweetest gifts.  We received everything from flowers and chocolates to spa days.  It truly didn’t matter what the actual gift was though, of course.  It was always the thought that counted.  I appreciate those memories more than ever now that my dad is gone.  Although those sweet days are behind me, my wonderful husband makes me feel just as special – one year he surprised me with a romantic getaway to  Miami!  Chicago is a very romantic city though.  If you are in need of a romantic date idea and live in or around the city, I’ve got you covered.  If you don’t live in Chicago, hopefully my ideas will inspire you to find something fun to do in your own city!

For the Pie Lover

Gaze into each other’s eyes over a slice of pie and coffee at Hoosier Mama Pie Company.  This pie shop is so adorably retro and unique.  They are open until 7 pm nightly, but close earlier on Saturdays and Sundays.  I know many city people eat later, but who says you can’t have dessert first?!  They also have Friday Night Flights where you can nibble on 3 different slices off of their menu, which usually has 5-6 choices available.

For the Thrill Seeker 

Blow your lover away with indoor skydiving at iFly in Lincoln Park.  Chris and I are dying to do this, but every time we plan it something comes up.  It looks really fun though!

For the Wine Obsessed 

Take your BAE to City Winery, Chicago’s first and only fully-operational winery, for a behind the scenes tour!  The tour includes an exclusive wine tasting not available to the public, a sample of City Winery made wine upon arrival, a tour of the facility, and a tasting flight of three City Winery wines paired with three crostini appetizers.

For the Show Loving Sweetheart 

Broadway in Chicago has a plethora of excellent shows happening right now.  My all time favorite show is Hamilton, but Men are from Mars – Women are from Venus Live is an excellent date night show.  Chris and I saw this with our friends last time it was in town and it was hilarious.  It starts back up on Valentine’s Day.  Also, The Bodyguard ends its Chicago run this weekend.  If a live performance is too expensive or the dates don’t line up, you might consider just going to the movies!  There are so many great shows out right now.  My preferred theater is Regal Webster Place 11 because their reclining seats are incredible and you can order adult beverages there.

For the Master Chef Wanna Be

Take a cooking class together!!!  I’ve taken classes at The Chopping Block and The Wooden Spoon and had a great time at both.  It’s always fun to learn something new and I’m pretty sure they are BYOB.

For the Starving Artist

First of all, feed them… haha.  Then, take them to do something artistic!  Some of my favorite artsy things to do are BYOB painting at Bottle & Bottega, painting pottery at Glazed Expressions, and spending the day at The Art Institute of Chicago.  If you don’t like these ideas go on Dabble to find a class that suites your significant other’s interest.

For the Dancer

Take dance lessons!  One of my favorite parts about wedding planning was taking dance lessons with my husband.  We went to Windy City Wedding Dance.  Don’t let the name deter you from going if you aren’t married.  They have lots of fun classes.  Check out their schedule here.  If you are getting married, you might consider taking lessons from Jessica.  She’s super nice and easy to learn from.

I feel like I could go on and on with awesome date night ideas, but I’m going to stop here.  Sorry there aren’t any pictures.  I’m actually writing this post on an airplane and the wifi isn’t that great.  What are some creative dates you’ve been on?  I’d love to know!  Leave me a comment below.

Happy Valentine’s Day, lovers!

XO, Lauren

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