There’s no denying Chicago is an easy city to fall for. With so many things to do, amazing arts and culture, a spectacular dining scene, and gorgeous architecture (among other things), getting swept off your feet just comes naturally in the Windy City. When romance is on your mind it’s the perfect place to organize an unforgettable evening, and Valentine’s Day 2024 is no exception — in fact, quite the opposite. Valentine’s Day in Chicago can be an experience like no other if you know where to go and what to do. We have several ideas on how to impress your sweetheart, and we are happy to share them with you to spread some love this holiday.




The Love Boat: Sail with City Cruises Chicago

Just like the theme song to the classic TV show The Love Boat, we believe love is life’s sweetest reward, so when you’re looking for something special for Valentine’s Day, we offer two enticing options: the Valentine’s Premier Plus Dinner Cruise on the Chicago River and the Valentine’s Premier Dinner Cruise on Lake Michigan.

Need more encouragement? Choose Chicago lists City Cruises Chicago as one of their favorite top romantic spot for your Valentine’s Day dinner.

couple on boat with heart balloonsThe Valentine’s Premier Plus Dinner Cruise on the Chicago River offers guests an enchanting evening under the stars complete with panoramic views of the spectacular Chicago skyline, its sparkling skyscrapers and celebrated local landmarks — including the DuSable Bridge, Willis Tower, Merchandise Mart, and more. You can capture them right in your sightline from our gorgeous glass-enclosed vessel with its climate-controlled interior and open-air decks. As you and your significant other cruise along the Chicago River over the next 2.5 hours, you’ll feast on a delectable, chef-prepared plated dinner and sip specialty cocktails. Our crew will provide you with top-notch service, while the onboard DJ sets the scene for slow dancing and romancing. Pro-tip: You can reserve a table by the window to ensure amazing views. You can also purchase creative cocktails, wine, and beer from our well-stocked cash bar, and add on additional upgrades to customize the experience. We’ll always do our best to meet any dietary restrictions, and in order to elevate the experience, we suggest you dress to impress because semi-formal attire is required.


Meanwhile, the Valentine’s Premier Dinner Cruise on Lake Michigan provides guests with an unforgettable opportunity to dine and dance as you travel along majestic Lake Michigan. With stunning views of the city’s beautiful skyline and Chicago’s amazing architecture (including celebrated attractions such as the Adler Planetarium and Navy Pier), you and the object of your affection will enjoy a decadent, chef-prepared plated dinner that is sure to satisfy your taste buds. There will also be innovative cocktails, wine, and beer available for purchase from a fully stocked bar, and games and music from the DJ onboard, take in the experience from our cozy climate-controlled interior, or open-air roof decks. Guests can expect 2-3 hours of making memories that will last a lifetime. The dress code is semi-formal attire, which helps set the mood for a classy and elegant evening. Window table reservations are available for the best views; additional upgrades can be made at checkout to customize the experience; and we’ll always do our best to accommodate any dietary restrictions.


Follow Your Heart to Chicago for Valentine’s Day 2024

big bus chicago live sunset tourIf you opt to spend part of your Valentine’s Day on land, Chicago has numerous ways to savor the experience. Whether you’re a foodie or cocktail lover, theater enthusiast or museum devotee, whatever your passion, this city will deliver it in spades. Not only is there a wealth of award-winning restaurants to try — as well as food tours to take — but there are shows to catch at the Chicago Theatre and exhibitions at renowned museums including the Art Institute of Chicago. For baseball devotees, a visit to Wrigley Field is a must, while those who adore architecture need only open their eyes to everything that surrounds them. Hotels, spas, and rooftop bars often offer specials during the holiday weekend, so that couples can make the most of their time here. We’d be remiss not to mention some off-the-beat ideas too, like heading to the Chicago Botanic Garden where instead of getting one bouquet of flowers, you can be surrounded by a multitude of amazing blooms, or ice skating in Millennium Park where you can glide in the shadow of one of Chicago’s most iconic landmarks, The Bean.


Book Your Valentine’s Plans in Chicago with City Cruises!

So what do we think is your best bet for making this the most memorable Valentine’s Day yet? Our vote is to combine a range of all of your favorite activities in Chicago (which we know would include a City Cruises experience!) along with everything else that quickens your pulse and makes your heart skip a beat. With so much to see and do, it may be a challenge to decide what your final itinerary will be, but all signs point to yes for success once you do.





What to do in Chicago for Valentine’s Day 2024? 

Chicago offers a variety of romantic activities for Valentine’s Day. A standout option is a Valentine’s Day cruise with City Cruises, where you can enjoy breathtaking views of the city skyline from the Chicago River or Lake Michigan. 

Are there Valentine’s Day cruises available in Chicago? 

Yes, City Cruises offers special Valentine’s Day cruises on both the Chicago River and Lake Michigan. These cruises provide a romantic setting with stunning city views, dining, and entertainment.  

What makes a City Cruises Valentine’s Day cruise romantic? 

The City Cruises Valentine’s Day cruise offers a unique experience with scenic views, gourmet dining, and dancing under the stars. It’s a perfect way to create unforgettable memories with your loved one.   

Can I propose during a 2024 Valentine’s Day cruise in Chicago? 

Absolutely! A Valentine’s Day cruise is a wonderfully romantic setting for a proposal. City Cruises can help arrange special details to make the moment even more memorable. 

What are some romantic things to do in Chicago on Valentine’s Day besides cruising? 

Besides a romantic cruise, Chicago offers many other Valentine’s Day activities like visiting the Art Institute, taking a stroll in Millennium Park, or enjoying a cozy dinner at one of the city’s renowned restaurants. 

What kind of dining options are available on a Valentine’s Day cruise? 

City Cruises offers an exquisite dining experience with a special Valentine’s Day menu, featuring gourmet dishes and fine wines to complement the romantic evening. 

Is there entertainment on the Valentine’s Day cruise? 

Yes, guests on the City Cruises Valentine’s Day cruise can enjoy live entertainment, creating a lively and romantic atmosphere perfect for the occasion. 

How long is the Valentine’s Day cruise and where does it go? 

The Valentine’s Day cruise duration varies, typically lasting a few hours. The cruise takes you along the picturesque Chicago River or around Lake Michigan, offering stunning views of the city skyline. 

Are there any special Valentine’s Day packages available with City Cruises? 

City Cruises often offers special Valentine’s Day packages, which may include perks like champagne, chocolates, or a private table for a more intimate experience. 

Do I need to book the Valentine’s Day cruise in advance? 

Yes, it’s highly recommended to book your Valentine’s Day cruise in advance as these cruises are popular and tend to fill up quickly. 


Original publish date: December 15, 2023