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Last Updated On: February 6, 2019

Valentine’s Day is not everyone’s cup of tea, however, if you are looking for something cute and different to do with your significate other around the 14th there’s actually quite a few fun and different things to do around the city. Here’s my list of the fourteen cutest things I found for you to do. Happy Valentine’s Day!

14 of the Cutest Things to do on Valentine’s Day in Chicago

Enjoy candy’s and cocktails at Cindy’s Rooftop Candies Pop-up Shop

From Wednesday, February 13th to Thursday, February 14th from 4 pm to 7 pm visit Cindy’s Rooftop and enjoy a special cocktail and shop sweet treats like chocolate bonbons and macaroons. Stay for card-making, cocktail toasting, and love letter-writing.

For the Love of Skating, Couples Skate at The Chicago Athletic Association Hotel

For $40 a couple you can skate and swoon along to classic jams. On Valentine’s Day, there are two sessions, one at 6 pm and one at 9 pm.

Dine at one of the best restaurants in Chicago at Maple & Ash

Enjoy a romantic dinner at one of the best restaurants in the city. My husband and I went last year and it was really, really great. Definitely, worth the $$$ and they don’t have a special menu for Valentine’s Day which I personally prefer. Make your reservation here.

Relax in ultimate luxury at Aire Ancient Baths

If you are looking for one of the best romantic spas in the city with a really luxurious experience than Aire Ancient Baths is a must. For under $100 per person, this will be one of the best spa experiences you will ever have.

Make dinner together at home and order a famous Portillo’s Chocolate Cake

For under $40, nothing says love like a giant heart-shaped chocolate cake!

Get tickets to the NAKED Scavenger Hunt at The Art Institute

Art lovers can explore The Art Institute and discover some of the coolest hidden secrets throughout the museum. You can grab your tickets here.

Plan a Chicago Staycation at some of the best hotels in Chicago

The winter is the perfect time to plan a Chicago staycation. You can get the best deals at some of the most luxurious hotels in the city. My favorite app to use for the best deals is the Hotel Tonight app.

Valentine’s Day with The Princess Bride at The Music Box Theatre

Movie-lovers can enjoy this classic movie at the iconic Music Box Theatre. You can get your movie tickets here.

See the lights of Chicago with a Helicopter Tour of the City

Chicago Helicopter Experience is having a few special Valentine’s Day deals. I’ve heard it’s the absolute best way to see the lights of the city. See all the specials here.

Enjoy Valentine’s Day Treats at Dylan’s Candy Bar

Chocolate lovers will enjoy all the chocolate treats at Dylan’s Candy Bar on Valentine’s Day. A perfect place to stop for dessert after a romantic dinner.

Listen to romantic jazz music at Winter Jazz Club

Enjoy a romantic night of jazz music and cozy up with a few cocktails. You can get tickets here or check the Gold Star app for discounts.

Plan a Valentine’s Day couples date with a Speakeasy Murder Mystery Cocktail Party

If you are looking for a fun couples date, then your group might love a little murder mystery. Tickets start at just $25 and you can get your tickets here and to read more about this event.

Fondue for two at Geja’s Cafe

Geja’s Cafe is probably one of the most popular places to go on Valentine’s Day because it’s really cozy and romantic and so well known for its amazing fondue. Make your reservation here.

Grab a box of Valentine’s donuts at Stan Donuts #donutdate

Donuts lovers will adore the special Valentine’s Day donuts. Get a box for your favorite donut buddy or plan a donut date.

14 of the Cutest Things to do on Valentine’s Day in Chicago 2019


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