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 Chicago Premier Plus Dinner Cruise on the Chicago River and the Chicago Signature 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.

The Chicago 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 cocktail attire is required.

couple on boat with heart balloons

Meanwhile, the Chicago Signature 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 dinner buffet of fresh entrees, salads, and desserts from our cozy climate-controlled interior and open-air roof decks. 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. Guests can expect 2-3 hours of making memories that will last a lifetime. The dress code is casual attire, so if the love that’s in the air inspires you to hit the dance floor, you’ll be able to do so in comfort and style. 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

If 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.


big bus chicago live sunset tour


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.