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Valentine’s Day 2024 in Chicago – Romantic things to do

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Visitors to Chicago love its cruises, exciting food, chequered history, and architecture, which is why it is an ideal Valentine’s Day destination. 

Young and old couples, visitors, and locals love spending Valentine’s Day in the Windy City.

If you adore your sweetheart (and we don’t doubt it!), you will want to spoil them with all the romantic surprises Chicago has to offer.

Plan ahead of time, for many lovers will be flocking to this city to celebrate the most romantic day of the year – 14 February 2024.

Check out our pick for the most romantic Valentine’s Day itinerary in the city with the best skyline in the world.

Things to do on Valentine’s Day in Chicago

Here are our recommended 16 romantic things to do during your Valentine’s Day week in Chicago.

You only need to bring your boyfriend or girlfriend along.

Enjoy a sunset cruise with your lover

Couple enjoying sunset cruise

Image: Wendellaboats.com

A sunset cruise lets you enjoy the beautiful Chicago architecture from the best vantage point.

After gliding over the waters, you will watch the sun slowly set behind the city from the tranquil waters of Lake Michigan.

This serene and romantic cruise is ideal for couples in love. 

Drinks and snacks are available for purchase on board.

If the cost doesn’t matter but the quality of the Valentine’s Day experience matters, check out this 2-hour private sunset cruise


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Get lovey-dovey on a dinner cruise

Lovers on dinner cruise
Image: Minerva Studios

Take a gourmet dinner cruise on a high-end luxury yacht against the backdrop of Chicago’s magnificent skyline.

Climb aboard the ship for your voyage along Lake Michigan, which features a beautiful rooftop lounge and a sophisticated interior design.

Then settle down for a three-course dinner prepared on board by one of the world’s finest celebrity chefs.

After supper, you can hold the hands of the person you love, look at the night views of Chicago, and listen to the onboard DJ.

The buffet dinner cruise is slightly cheaper than the gourmet dinner cruise.

Some couples opt for the lunch cruise and plan something else for the evening. Lunch cruises cost only half of what dinner cruises cost. 


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Go in search of Chicago’s best food

Chicago food tour

Elders have said, “The way to his heart is through his stomach,” the same can be said for the way to her heart. 

That is why one of the best ways to celebrate Valentine’s Day 2024 in Chicago is to go on a food tour.

On these tours, a local food expert helps you experience the food and culture of the city. 

If you and your lover are foodies, we recommend you opt for one of the numerous tours.

TourCost
Chicago West Side Foodie Cycling Tour$92
Chicago Pizza tour$77
Chicago’s Signature Dishes Bike Tour$92
Underground Donut Tour$56

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Try Chicago’s popular Architecture Cruise

https://www.youtube.com/watch?v=Sou1G_Q3SQc

Chicago is known to have one of the world’s best skylines, and its architectural tours are popular with tourists. 

Why don’t you cruise down the Chicago River this Valentine’s Day to see the famous architecture?

The tour comes with a commentary from your onboard guide, who narrates stories about each building. 

Offered several times throughout the day, it’s easy to fit the leisurely excursion into your Valentine’s Day itinerary. 

TourCost
Chicago Architecture River Cruise$48
90-Minute Chicago River Architecture Tour$45
Chicago Lake and River Architecture Tour$45

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Book a private helicopter tour

Helicopter tour over Chicago
Lisa-Blue / Getty Images

This helicopter tour is ideal for couples who need something extraordinary to make their Valentine’s Day memorable. 

During this 45-minute tour, you take sweeping views of Chicago from the air and look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. 

It is also an excellent opportunity for stunning photo ops on the ground and in the air. 

If this is too costly for your taste, check out the indoor skydiving in Chicago, which offers a similar adrenalin rush.


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Learn about the Underworld

Husband and wife pose during mob tour
Husband and wife pose during a mob tour in Chicago.

Even today, Chicago is considered the most gang-infested city in the United States. 

Now imagine how it must have been in the 1920s when the gangs peaked. 

If you and your partner love history or mystery, you will love to learn about the Chicago underworld. 

There are two ways to learn about the bootleggers, speakeasies, and gangsters like the infamous Al Capone – the walking or the coach tours. 

During these tours, you will also visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.


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Get an adrenalin rush on Speedboat

This fast-paced speedboat ride will surely get your heart beating and includes a healthy dose of history, humor, and facts.

You listen to roaring music and the engines as your 2,000-horsepower craft zips along the lake on its way to an adrenaline-pumping tour.

Zoom down the shoreline of Lake Michigan on a fantastic speedboat excursion in Chicago, whizzing by iconic sites along the way.

The speed-infused adrenalin rush will bring both of you closer, so don’t miss it!


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Get classy at the Art Institute of Chicago

The Art Institute of Chicago has the most extraordinary Impressionist collection outside Paris.

It is the only museum in the world to be top-ranked by TripAdvisor for four years and is the Number 1 thing to do in Chicago.

It may not be the traditional way to celebrate Valentine’s Day in Chicago, but why not if you and your partner love art?


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Get romantic on a lakefront cruise at night

Beautiful night cruise on Chicago lake
Image: GetYourGuide

Witness the magic of Chicago at night as the city’s magnificent skyscrapers and ancient structures come to life with millions of glittering lights.

This evening cruise begins on the picturesque Chicago River.

It then takes you through the Chicago Harbor Lock and out onto Lake Michigan, where you can enjoy panoramic views of the city’s beautiful skyline and shoreline.

If you have Valentine’s Day activities planned for the day, this nighttime cruise is the perfect way to relax and unwind with your partner for life. 


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Go pub-hopping with your partner

Pub hopping with partners

If you love beer or pub-hopping, the Chicago Craft Brewery Barrel Bus Tour is the best way to celebrate Valentine’s Day with the person you love. 

You will travel from brewery to brewery in a Prohibition-era-styled barrel bus. During the tour, learn about the history of Chicago’s beer industry, which originated in the 1800s. 

This tour is open only for 21+ year-olds, and couples must show a valid ID to join. 

Your tour ends at the pickup location, after which you can hop into any pub and continue your romance. 


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Try out a Segway tour of the city

Loving couple on Segways
Image: Chicagosegways.com

See many of the city’s top sights on a 2-hour guided Segway tour of Chicago.

You will get started on your self-balancing Segway after a 30-minute orientation on using the future means of transportation.

During this tour, a local expert will guide you along a scenic 13 km (8 miles) route. 

It is an ideal Valentine’s Day activity for young couples looking for something different. 


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See the city from an observatory

Table for two at 360 Chicago
Couples love to spend intimate moments at Bar 94, Chicago’s highest bar, with a full 360-degree view of the city. Image: 360chicago.com

Chicago’s skyline is one of the world’s most stunning, easily ranking among the world’s highest. The city is home to four of America’s eight highest structures.

Two of the most famous observatories in Chicago are – Skydeck Chicago and 360 Chicago.

From the massive glass windows of their observation decks, you fully appreciate the city in all directions. 

To increase the romance quotient, be at the observatory after dark – with all its lights on, Chicago is glittering below, and with fewer people, you get some privacy. 

Not sure which observatory to visit? Check out our comparison Skydeck Chicago or 360 Chicago.

If you would also like a drink at 360 Chicago, check out this ticket.

The Navy Pier Centennial Wheel offers unparalleled 360-degree views of Chicago and Lake Michigan at a much lower price. 


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Roam around aimlessly with your love

Take a hop-on, hop-off bus tour of Chicago that highlights centuries of history. 

Depending on how long you want to stretch your Valentine’s Day week, you can choose from 1-day or 2-day tickets. Or night tour tickets. 

This tour is ideal for spending time with your loved one because of the flexibility – you decide when you board and when to get off.


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Visit the Field Museum of Natural History

If you and your partner are history buffs, don’t miss out on a Valentine’s Day visit to Chicago’s Field Museum – it’s a must!

The museum boasts 26 million artifacts, including the world-famous SUE, the largest T. Rex ever discovered. You’ll feel time-traveled as you explore thousands of years of history.

Check out the rare jewels and the dazzling Hall of Gems, and observe Field Museum Scientists in action on ancient specimens.

It’s the perfect way to spend your Valentine’s Day in Chicago.

Engage in Art Together

Spend a unique and creative Valentine’s Day at Studio W.I.P. in Chicago with a BYOB Spray Paint ‘n’ Sip session.

This artistic experience offers a delightful twist on the traditional romantic date night.

Grab your favorite bottle of wine or beverage, and let your creativity express love to your partner.

Explore the world of art together under the guidance of talented instructors.

Experiment with stenciling and spray-painting, and craft your masterpiece on canvas to take home.

It’s an ideal way to celebrate love and creativity on this special day.

Explore Indoor Skydiving

Experience the thrill of freefall without ever stepping foot on an airplane at Lincoln Park Indoor Skydiving.

It features two thrilling flights and a personalized certificate.

Share the excitement as you both float and fly in the vertical wind tunnel, feeling the rush of freefall together in a safe and controlled environment.

Whether celebrating your first Valentine’s Day as a couple or looking to add some adventure to your long-lasting romance, this unforgettable indoor skydiving adventure will create lasting memories.

Chicago CityPass for more attractions

What can be more romantic than not worrying about the cost and roaming around Chicago freely?

Imaginative romantic couples go for a Discount Pass, which helps them get more out of less during Valentine’s Day in the Windy City. 

The Chicago CityPass helps tourists and locals see must-see attractions and save money. 

So, how do you and your love plan to celebrate Valentine’s Day 2024 in Chicago? 

Book ahead before your options run out – it is another way to show that you care. 

Best US Cities for Valentine’s Day Celebration

BostonMiamiNew Orleans
ChicagoLas VegasSeattle
PhiladelphiaSan FranciscoOrlando
San DiegoNew YorkLos Angeles
San AntonioDenverAustin
TampaNashvilleHawaii
HoustonMinneapolisDallas
AtlantaCharlotteCleveland
PittsburghSt. LouisDetroit

Additional Reading

Valentine’s Day in Paris
Valentine’s Day in Venice
Valentine’s Day in Barcelona
Valentine’s Day in Amsterdam
Best honeymoon places in the World
Romantic places to take your girlfriend or wife

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This article was researched & written by

Edited by Rekha Rajan & fact checked by Jamshed V Rajan

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