Top Valentine Day Destinations in Chicago

Famous Chicago landmarks and attractions
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Valentine’s Day is the perfect time to plan an unforgettable date with your special someone. Whether you’re looking for a romantic dinner or an exciting activity to share, Chicago has plenty of options to choose from. From cozy cafés and romantic dinner cruises to thrilling outdoor activities and much more, there is something for everyone in the Windy City. To help you make the most of your Valentine’s Day, here are our top Valentine Day destinations in Chicago.

1) Sky Rink Of Peninsula

Valentine’s Day is the perfect time to spend some quality time with your special someone. Whether you want to spend the day in a romantic setting or are just looking for something fun to do, the Sky Rink Of Peninsula is the perfect place for you! Located in Chicago, the Sky Rink Of Peninsula offers ice skating for all skill levels. Whether you’re a beginner or a pro, there is something for everyone at the rink. Skaters can enjoy breathtaking views of the city skyline while they skate, as well as being surrounded by music and a festive atmosphere. There are even special Valentine’s Day packages available that include things like hot chocolate and snacks. Spend your day with your special someone on the ice, enjoying a unique and unforgettable experience!

2) Auto Show

For an adrenaline-filled Valentine’s Day, head over to the Chicago Auto Show. This event features cars of all shapes and sizes, from classic cars to modern luxury models. Get a behind-the-scenes look at the production of cars and learn how they are designed and built. Tour the showroom and see the latest in auto technology. You can also take part in educational events hosted by industry experts. It’s a great way to bond with your loved one over your mutual appreciation for cars!

3) Signature Room

The Signature Room at the 95th floor of the John Hancock Building is the perfect place to spend Valentine’s Day with your special someone. Boasting breathtaking views of the city, it is one of the most romantic places in Chicago. From cozy, romantic dinners to tasting fine wines, this is the perfect place to make unforgettable memories with your significant other. The restaurant serves classic American dishes with a modern twist, as well as an extensive list of top-notch wines and drinks. Enjoy a quiet dinner or dance to live music while sipping on delicious cocktails with your beloved. The Signature Room is definitely a place to make your Valentine’s Day extra special.

4) Chopping Block

If you’re looking for a fun and romantic experience for Valentine’s Day, the Chopping Block in Chicago is the perfect spot for you. Offering couples classes, team-building activities and private events, the Chopping Block allows couples to learn together and bond through cooking. Classes are held in either their state-of-the-art kitchen at the Merchandise Mart or their cozy Lincoln Square location. Learn a new cuisine together, or brush up on your favorite cooking techniques with their variety of classes like French Classics or Indian Cuisine. Spend your Valentine’s Day chopping, stirring and sipping your way to a tasty dinner, followed by a romantic night out in Chicago.

5) Riverwalk

Chicago’s Riverwalk is a fantastic destination for lovers to explore together on Valentine’s Day. This scenic route along the Chicago River offers breathtaking views of the city skyline and a great opportunity to take romantic strolls hand-in-hand. You can stop at any of the many restaurants, bars and shops along the way, or simply enjoy the sights and sounds of the city around you. Whether it’s a leisurely walk or a romantic dinner for two, the Riverwalk is sure to make your special day even more memorable.

6)  Magic Tricks

Valentine’s Day is a day for love and romance, but it can also be a day for fun and adventure. If you’re looking for an activity to do with your special someone that’s sure to bring some excitement to your Valentine’s Day, why not check out some magic shows? There are a few places in Chicago that offer some magical entertainment.

The House of Magic is one of the most popular locations for those seeking a night of entertainment. Located near the Loop, the venue offers shows from some of the world’s best magicians. Their shows feature acts such as vanishing acts, mind-reading illusions, and more. With tickets starting at just $15 per person, it’s an affordable way to experience some of the most amazing performances in the city. 

If you’re looking for something a bit more low-key, you could always check out the Amateur Magic Club of Chicago. Located in Lincoln Park, the club is home to amateur magicians of all ages who practice and perform tricks in front of an audience. The club also offers classes and workshops for those looking to learn how to perform their own tricks. It’s free to watch the show, so why not go and enjoy a night of fun and laughs? 

Finally, there’s the Chicago Magic Lounge. The lounge is a place where experienced magicians show off their skills in an intimate setting. With up-close performances and interactive tricks, it’s sure to be a night to remember. Tickets start at $25 per person and they offer different packages depending on what type of show you’d like to see.

No matter what kind of magic show you’re looking for, you’re sure to find something that suits your taste in Chicago this Valentine’s Day. So go ahead and explore the possibilities – it could be the perfect way to spend a magical night with your loved one!

7) Dinner Cruise

For a romantic night out this Valentine’s Day, consider taking your special someone on a dinner cruise around the beautiful Chicago skyline. You’ll get to take in views of the city’s iconic buildings from a different perspective, while enjoying an exquisite dinner and drinks with your partner. Cruise companies such as Odyssey and Spirit of Chicago offer luxurious Valentine’s packages including a three-course meal, live music, and dazzling views. Other options include champagne cruises and intimate cruises for two. A dinner cruise is the perfect way to show your loved one how much you care this Valentine’s Day.

8) Horse-Drawn Carriage Ride

A horse-drawn carriage ride is the perfect way to make your Valentine’s Day special! A romantic ride through the streets of Chicago is sure to be a memorable experience. There are several companies offering horse-drawn carriage rides, and they usually provide blankets, blankets and snacks so you can enjoy your ride in comfort. You’ll get to see some of the city’s most beautiful sights as you go along. Whether it’s a surprise romantic gesture or a fun outing for two, this is a great way to make your Valentine’s Day one to remember.

9) Parade

For those looking for a unique and exciting way to celebrate Valentine’s Day, a parade is the perfect way to do it. With a variety of exciting activities and performances, Chicago is home to some of the best parades around. On February 14th, the city will be filled with music, dancing, and of course, lots of love. As you make your way through the streets, you’ll be able to experience beautiful floats and themed performances that will make you feel like you’re in a fairytale. The parade typically starts at Daley Plaza and goes throughout the city for over two hours. Not only is this a great way to show your affection for one another, but it’s also a great way to take in the sights and sounds of the city. So grab your Valentine and enjoy a romantic stroll down memory lane as you explore the magic of Chicago!

10) Navy Pier

Navy Pier is an iconic Chicago landmark located on the city’s Lake Michigan shoreline. It is home to a variety of attractions and activities, making it a popular spot for visitors and locals alike. On Valentine’s Day, Navy Pier has something special in store. 

Visitors can enjoy some romantic activities with their loved ones at Navy Pier, such as taking a romantic stroll along the pier, enjoying the beautiful views of Lake Michigan, or indulging in a delicious meal at one of the many restaurants located here. 

Valentine’s Day at Navy Pier also includes special events and performances like music concerts, theatre shows, fireworks displays, and art exhibits. There are also plenty of rides and attractions to explore. From a breathtaking ferris wheel ride to thrilling carousels and carnival games, there is something for everyone to enjoy. 

On top of all that, Navy Pier offers some of the best shopping experiences in the city. With stores ranging from luxury brands to small boutiques, shoppers can find unique gifts for their loved ones. Plus, there are several specialty shops featuring local goods, such as artisanal jewelry and crafts.

Whether you are looking for a romantic night out or just a fun-filled day exploring all the activities Navy Pier has to offer, this is the perfect destination for Valentine’s Day.

Final Words

No matter what your idea of a perfect Valentine’s Day is, Chicago is the perfect place to celebrate. Whether you’re looking for a romantic dinner, an activity-filled day, or something unique and unexpected, there are plenty of options in the Windy City. From taking in the skyline from a rooftop rink to horse-drawn carriage rides through the city, Chicago has everything you need to make your Valentine’s Day special. Don’t forget to take in some of the city’s most beloved landmarks and attractions, like Navy Pier and the Riverwalk, for a truly unforgettable experience. So grab your sweetheart and enjoy a memorable Valentine’s Day in Chicago!

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