How to Spend a Special Valentine’s Day in Chicago

How to Spend a Special Valentine’s Day in Chicago

Valentine's Day is special to every couple out there. There are always events on for the love birds out there and Chicago is no exception. Have a look at our special events to attend in Chicago

About Valentine’s Day

Every year, the 14 of February becomes a day where lovers exchange gifts, flowers and everything in between. It is a day where everyone is meant to love each other. Although it has become a commercial day, Valentine’s Day does in fact have a level of history to it. The day, named after St. Valentine, has spread across the world to form a number of traditions. But how did it all start? Nobody really knows! Valentine’s Day and February as a whole has become the month of romance. It is thought that Valentine’s Day could have started in the Catholic church as it recognises at least three different Saints named Valentine however nobody can be 100% sure.

Although none of us can actually prove where Saint Valentine or Valentine’s Day came from, most of us still cherish the day we have with the special person we love. As much as we can all probably agree that we should show how much we love someone on a daily basis rather than on a particular date it is still quite a nice reminder. The 14th February has become a tradition of sharing and proving love to someone as well as an excuse for a day of romance! Below are some suggestions about how you could spend your Valentine’s Day if you are in Chicago.

Top List of Things To Do During the Day on Valentine’s Day in Chicago

For those of you who want to spend a whole day with your one true love, there are a number of activities to explore in Chicago. Below are some of the top suggestions we have for you!

Dirty Dancing Class at Duet Dance Studio

A very popular event amongst couples, the Dirty Dancing Class is a great way to have a passionate moment with your other half. The class is a themed party that will allow you to learn how to dance like Johnny and Baby in the movie Dirty Dancing. You will be able to woo your lover with a fifty minute class that will teach you basic salsa dance steps, basic leading and following as well as a simplified Dirty Dancing routine. The Dirty Dancing session is a beginners class that will be held at the Duet Dance Studio at 2515 W North Ave in Chicago. The class is priced at $85 per couple plus fees. Because it is such a special occasion, Duet Dance Studio encourage you to bring your own bottle of beer or wine to loosen up your dancing feet.

Enjoy the Romance of the Theatre in Chicago

If you or your partner love the theatre there is no better time to indulge in a romantic show then on Valentine’s Day. We have two suggestions for you. The first option is A Widow of No Importance which is a Romantic Comedy by playwright Shane Sakhrani. This story is great for those who love a good mushy love story. It is about a widow who loses herself in her daughter’s love life before falling in love and understanding the importance of life again. A Widow of No Importance will be screening from February 11 to the 21, 2016. the Valentine’s Day screening is at 3.30pm which gives you plenty of time to head out for a romantic meal afterwards.

Our second suggestion for Valentine’s Day would have to be Animals Out of Paper by playwright Rajiv Joseph. This story is quite uncommon and depicts the fragility of happiness, hope and impulsiveness through three main characters. The show is being shown from February 11 to February 14, 2016. Once again the Valentine’s Day screening of this show will be at 3pm so you can make dinner reservations as well.

A Valentine’s Day Cruise at Navy Pier

If you are looking for some good, old, traditional romance, treat your loved one to a cruise from Navy Pier. If the weather allows it, there is nothing better than cuddling up whilst enjoying the fresh breeze of the beautiful ocean. The Valentine’s Day themed cruises are a combination of light comedy, incredible food and of course a lot of romance. If you cannot attend a cruise on the official day then do not worry as Navy Pier are running Valentine’s Day themed cruises from the 13 to the 15 of February, 2016. For more detailed information about the each days events head to

Join the Fun at Love Cork Screw Valentine’s Day Tour

If you want to experience some of the great wining and dining locations in Chicago this may be the perfect tour for you. Love Cork Screw are a wine lifestyle company that basically teach people about social events, wine and generally how to have a good time. Love Cork Screw will take you on a tour of some of the most popular restaurants in Chicago. you will be greeted at a post event reception and then taken on a private tour with private chartered transportation. There will be four stops with exciting tastings at each location. In order to not interfere with your Valentine’s Day plans, the event will take place on Saturday 13 February 2016 from 1pm to 5pm.

Falling Hearts Event

Falling Hearts is a Valentine’s Day special event brought to you by Fourtune, Haywood, MCclain and Madlock. The event is pretty straightforward but will most likely be executed with a high level of class and consideration to make sure your romantic evening is perfect. The evening is a night of beautiful food and incredible entertainment from some of the hottest acts Chicago has ever seen. The combination of beautiful, soulful music and amazing quality catering will be a night to remember. The Falling Hearts event is being held at the Latvian House on 8845 West Lynx Avenue Milwaukee on February 13, 2016 from 6.30pm to 9pm. Tickets are available at the price of $16.82 per person for general admission and $27.37 per person for VIP seats.

Best Places for a Romantic Dinner on Valentine’s Day in Chicago

Of course you cannot finish Valentine’s Day Properly without a special, romantic dinner in place. We have looked through the mounds of restaurants in Chicago and come up with our list of top five romantic restaurants you just have to try and get a seat at on February 14, 2016.

Gaetano’s & Ristorantino Mediterraneo

Although the details of this luscious Valentine’s Day menu have not yet been revealed to the public we are 100% sure they will be special. Chef Gaetano Di Benedetto is a native of Sicily. He cooks some of the most amazing food in Chicago and has been the proud chef of restaurants in capitals such as Paris, London, Milan and the list goes on. For Valentine’s Day he is cooking up a new fixed menu for lovebirds to come and enjoy. You can find Gaetano’s & Ristorantino Mediterraneo at 7636 W. Madison St. Forest Park and details about the new menu will be online very soon!

The Capital Grille

For the lovers of fine wine and tender meats as well as fresh seafood you may have just found the restaurant version of heaven. Not only will you be served exciting and beautifully cooked food but the service is to die for. It is really a “special occasion” kind of experience. Let’s be honest, there is no better time to book a table at one of the top rated restaurants in the city than Valentine’s Day. The Capital Grille aim to dazzle you with attention on Valentine’s Day so be sure to book your table as soon as possible. Capital Grille can be found at 633 North Saint Clair.


Be dazzled by the flavours of France by joining Brindille for your special day out with your one true love. Nothing says romance better than France so why not book at a table at Chicago’s most renowned and well established French restaurants. The chef cooks the most refined Parisian food and of course the wine selection is to die for. The award winning chef and owner of Brindille, Carrie Nahabedian will be serving the usual a la carte menu as well as a tasting menu. Brindille can be found at 534 N. Clark St, Chicago.


For something a little more exotic you could book a table at Miga. Miga is a modern restaurant that serves American food with perfectly distributed Asian infusions. If you are looking for something that is affordable but offers incredible, quality ingredients cooked well then you have hit the jackpot. The chef brings together his experience of French, American and Asian cuisine into amazing dishes. His amazing amount of experience has allowed him to offer a seven course tasting menu for all the lovers looking to book a table at Miga. Miga can be found on 301 N. Neil St. in Downtown Champaign.


For those that pay great attention to ratings you may want to know that Boka is a Michelin Starred restaurant that has been at the top of Chicago dining for over 12 years. Lee Wolen, Executive chef and Partner changed the way the restaurant worked in 2014 and trust us it has not gone unnoticed. He was named Chef of the Year in 2014 and 2015. the food served at boka is a blend of American cuisine that uses only the best quality, local ingredients.

Not only is the food to die for but the presentation is without a doubt the best you will see in the city. Simply Beautiful. Although there will be no A La Carte menu available on Valentine’s Day, the chefs have put together a six course tasting menu for $125 per person as well as optional wine pairings for an extra cost. Boka can be found at 1729 North Halsted, Chicago.

10817892 764402490276105 1781621198 n
“Our Octopus with chestnuts and plum 🐙”

Some More Unusual Suggestions for a Valentine’s Day in Chicago

How about a Naked Scavenger Hunt?

Before we explain this event to you, do not worry you do not actually have to be naked to join in. The idea behind the Naked Scavenger Hunt is to hunt for nudity at the Art Institute of Chicago. You will go through the museum looking at all the paintings, sculptures and objects in great depth to try and find all things relating to nudity. It may sound strange but imagine running around like a puppy love infected kid with your one true love! Doesn’t sound too bad after all, now does it? The event is for adults only and takes place on February 14, 2016 at 11am or 2pm. The Naked at the Art Museum Scavenger Hunt will start at the Art Institute of Chicago. The tickets are priced at $38 per person which includes admission to the museum.

For the Sporty Couples Out There- Cupid’s Undie Run

This may sound like a bit of an odd way to spend your Valentine’s Day but why not ey? Cupid’s Undie Run is perfect for the sportier couples out there that enjoy a more adrenaline pumped activity just before Valentine’s Day. You will join hundreds of runners to raise money for the children’s Tumor Foundation. It is not much to ask either as the run is actually just one mile long. The Undie Run actually takes place on the 13 February and the earlier you book your spot the more likely you are to pay the early bird prices. The party kicks off at noon, followed by the Award Ceremony at 1pm. At 2pm the Undie Run will begin. You do not have to run in underwear although it is highly recommended to add a bit of a fun factor to the day. Once the run is complete there is an open bar until 3.30pm and the event ends at 4pm.

Make your Idea of Eloping a Reality

So many of us dream of getting married on Valentine’s Day but just never get around to it. Well, why not live in the moment this year? It may sound strange but it is now possible for you to just go ahead and get married on the most romantic day of the year. If you want a quick, fun elopement then why not head down to the Downtown office and just jump in feet first? You can buy your ticket right now on the Eventbrite website for just $149 per couple. Now that has to be one of the cheapest weddings you have ever heard of! Tickets are available for February 14, 2016 between 10am and 7pm. you will be allocated a slot and will be able to bring at least five guests. The elopements are taking place at Indy Wedding Centre on 711 South Street.

Find the Buddha in you with your Partner

Some people may see this as an obvious option whereas some will think it very strange. Not only, will you be able to spend some time up and close with your other half but you will learn about the benefits of having a partner in your yoga practice. Elite Training and Fitness at 1479 Market Street in Des Plaines is offering couples yoga at just $30 per person plus fees. The workshop is three hours long and will encompass everything you need to know about your practice and your relationship. It will symbolize trust and love which are feelings all of us should feel at some point in our lives. If you want to reignite the flame of love, trust and passion between you and your lover there is no other way of doing that at the couples fitness workshop in Les Plaines.

Valentine’s Day Paint and Sips for Couples

Whether you are an established artist or just want to have a bit of fun and do something a little bit different, Valentine’s Day Paint and Sip for Couples will be sure to provide you with a level of entertainment this Valentine’s Day. Couples will work together and be taught how to paint a representation of another painting. The painting they are going to be asked to represent is two canvases of red wine pouring into a glass. It sounds strange but bare with us! Not only do you get the chance to create a beautiful piece of art but you will be rewarded with loads of lovely treats and surprises throughout the day. You will be provided with all the materials. All you need to do is bring a bottle (or two) and your sweetheart. The event is on February 13, 2016 from 6pm to 10pm at Fabric, Fiber and finds on 5150 North West Highway Crystal Lake.

In the Key of Love Event

In the Key of Love will most likely not be suited to everyone. If you do not like jazz it is already a no go. On the other hand if you love jazz you may going down the right path to the perfect Valentine’s Day event. In the Key of Love is a Jazz Concert run by Da’Ja Entertainment. The event is a combination of great food and awesome music by John Smith, Da’Ja wsg., The Fantastic Four and God’s Dynasty. In addition to this already incredible lineup of entertainment there will be a live comedy act from the one and only Russell Rabb. In the Key of Love Jazz Concert is taking place on the 13 February 2016 at The Vault which can be found at 3800 W Chicago St. Redford Charter Twp on the campus of Detroit World Outreach. Tickets are on sale now and vary in price. VIP tickets which include VIP seating, Strolling Buffet and a gift bag with an autographed CD by Da’Ja are $43.19 per person. General Admission are $22.09 per person and include the strolling buffet. VIP couples special tickets which include two VIP tickets are $32.64 per couple. Ticket sales end on the 23 January 2016.

Other Great Suggestions you Could Have a Look At

If you are sick of looking at all the loved up couples snuggling and being happy come and join some other like minded people that just want to go and have some fun. Bar1 Events Inc. have ran this event 16 times before so you can be guaranteed some fun. The event is taking place on February 13, 2016 from 8pm to 11pm. The $20 ticket includes food buffets at each bar, domestic drafts, Cupid Punch and transportation to all four bars.

Other singles events include Valentine’s Day Speed Dating presented by SpeedChicago Dating amongst many others. There is really something for everyone in the city of Chicago during the Valentine’s Day period. The beauty of it is that most events cater for singles too so you can go and maybe even meet your match. For more information on Valentine’s Day events across The United States have a look at some of the other Daring Penguin events lined up this year.

Related Articles

This article is also popular ♪

Christmas in Chicago: Sage Advice on Spending the Holidays in the Windy City

Christmas in Chicago: Sage Advice on Spending the Holidays in the Windy City

12 Can't-Miss Events at Navy Pier, Chicago

12 Can't-Miss Events at Navy Pier, Chicago

10 Annual Events To Help You Experience Millennium Park All Year Long

10 Annual Events To Help You Experience Millennium Park All Year Long

How to Best Spend Your Chinese New Year in Chicago

How to Best Spend Your Chinese New Year in Chicago

9 Reasons to Choose Chicago for Your St. Patrick's Day Festivities

9 Reasons to Choose Chicago for Your St. Patrick's Day Festivities

Find articles from keywords

This article was written by:

Category list

Report about the content.

About Daring Penguin | Inquiries | Privacy policy | Terms of use

Plan and book your perfect trip with expert advice