12 Things to Do in Chicago for Valentine’s Day (2020)

If you are visiting Chicago in February with your special someone, here are some ideas for romantic things to do in Chicago for Valentine’s Day.

1. Enjoy stunning views of Chicago at the Signature Room

On top of the 875 N. Michigan Ave Building (more commonly known as the Hancock Building) on the 95th floor you can take your date to the top of the clouds and have brunch, dinner, or cocktails at the Signature Room

They are famous for the extravagant brunch buffet that includes many options and endless chilled seafood like shucked oysters, shrimp, crab legs, and smoked salmon. 

If you’d prefer an evening of indulgence, their dinner menu is also very tempting. Many visitors will head up for a cocktail to sip and enjoy the view. Be sure to make reservations for a meal! 

2. Go Ice Skating in Millennium Park 

What’s more cinematic than ice skating with your crush in the gorgeous Downtown Loop? There are several places to skate on Valentine’s day. 
 

 

Most rinks have free admission through February and provide skate rentals for just $12. 

3. Join the Lincoln Park & Gangster Tour

Ever heard of the St. Valentine’s Day Massacre?  A little macabre, yes, but if you and your partner in crime are interested in history- this could be a great choice!

 

Bundle up and join our Lincoln Park & Gangster Tour on Valentine’s Day to learn all about Al Capone and his V-Day plans for February 14th, 1929.

4. Check out the Cupid’s Undie Run

On February 8th, you can enjoy a Cupid Themed fundraiser!  It is a 5k where participants run in their undies and benefits finding a cure for neurofibromatosis (NF).

Party at John Barleycorn at noon, run at 2pm, and return to celebrate some more! More information about Cupid’s Undie Run, including registration/volunteering can be found on the website.

5. Live Music

 

There is nothing more romantic than sipping a martini while tapping your foot to a live band.

If you are alone during the V-Day season, perhaps you’d prefer listening to the blues.  Here are some of our favorite places.

6. Eat Your Heart Out

 

Many restaurants have created an exclusive menu for Valentine’s Day Weekend, and OpenTable has some listed here.

It might be overwhelming to see all of the choices, but OpenTable lets you choose the perfect restaurant based on cuisine and location, and gives you access to hundreds of reviews! 

Here are Chicago Tribune’s favorites.

7. See a Show

There will be a lot of options for live entertainment on February 14th!   Here are a few “love” themed options!

  •  You can check out the Laugh Factory to see the comedic line-up entitled “My Funny Valentine.” 
  • Mortified is a company that has actors share embarrassing stories about their childhood and does a few shows a year in Chicago- one is usually on Valentine’s Day.

 

 

8. Valentine’s Day Dinner Cruise

A special way to treat yourself is to book a Valentine’s Day Dinner Cruise.

Most boat rides last about 2-3 hours and include a meal and often have a D.J. 

 

 

There are several other options but be sure to make your reservations early since it will be quite popular! 

9. Ride the Centennial Wheel

Head over to Navy Pier with your date for a gorgeous view of most Tour Guide’s Love: Chicago! 

 

 

Riding on the ferris wheel is fun, historic, and also HEATED.  The updated attraction added air conditioning for the summer and heating for the winter.  So you can enjoy a romantic moment and not completely freeze.

10. Take a Dance Class

Dance the night away with your love at Duet Dance Studio’s Valentine’s Day Dance classes. 

 

 

They are offering a Dirty Dancing themed event as well as a Grease themed event.  Either way, you will be down to boogie.

11. Go to a Haunted House

Because what is truly more perfect that to either scream into the arms of your honey or to just scream on February 14th? 

 

 

Love Bites is an amusing and fun haunted house which could be the perfect way to spend your February.

12. Valentine’s Day with your Kids

If you are looking for something to do with the whole family, be sure to check out the Chicago Park District’s site. 

Valentine's Day with Kids in Chicago 2020

They host Valentine’s Day activities for kids all across Chicago!


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About the author

Manager | Chicago & Los Angeles

Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!