Celebrate Love in the States: 15 Ways to Enjoy Valentine’s Day in Chicago 2023.

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Agree or disagree but one thing is definite— Valentine’s Day can be a bit stressful. The Valentine’s Day bar has been set quite high between selecting the flawless dining venue to choose the ideal gift. Fortunately, you have Chicago to rely upon. There’s always something pleasant to do in a town like this. Why don’t you try something unique this year as you celebrate Valentines Day in Chicago? This Valentine’s Day, skip stale candy hearts and cheesy greeting cards and create lifelong memories! Experience the alluring side of Chicago with our suggestions for the coziest restaurants, romantic hotspots, and some wild cards!

valentines day in chicago

15 Things To Do On Valentines Day In Chicago

If you visit Chicago in February with someone special, here are a few ideas for romantic things to do on Valentine’s Day in Chicago. So, check this list out for making this day more special for you and your beloved.

  • Sky Rink Of Peninsula: Skate Smoothly!
  • Auto Show: Take A Test Ride In Chicago!
  • Signature Room: Experience Amazing Views Of Chicago!
  • Chopping Block: Mix Stuff In The Kitchen
  • Riverwalk: Go For A Romantic Stroll!
  • Magic Tricks: Be Astonished!
  • Dinner Cruise: An Exotic Affair!
  • Horse-Drawn Carriage Ride: Explore The Town!
  • Parade: Step Out In Chinatown!
  • Navy Pier: Go For A Walk Or A Ride!
  • Field Museum: Have An Encounter With History!
  • Maggie Daley Park: Go On A Relaxing Stroll!
  • Chicago Boat Tour: Sail Away!
  • Bottle & Bottega: A Romantic Painting Class!
  • AIRE Ancient Baths: A Soothing Evening!

Be smooth at the Sky Rink of Peninsula

1. Sky Rink Of Peninsula: Skate Smoothly!

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Skate at the top of the world at the incredible Sky Rink of the Peninsula hotel— a rooftop rink overlooking the stunning Magnificent Mile in Chicago. Then cuddle in one of the ventilated lounge areas and relish warm chocolate, mulled wine or apple cider from The Chalet. The Rink is open to visitors to the hotel, restaurant, or spa on the peninsula every day. Skating at the Sky Rink is one of the most captivating things to do with your bae on Valentine’s Day in Chicago in 2022.

Essential Read: Honeymoon In Chicago: 10 Remarkable Ideas To Have The Most Special Time With Your Bae!

Take a test ride at the Auto Show in Chicago

2. Car Show: Take A Test Ride In Chicago!

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Marvel at automobiles and daydream about your next journey on the Chicago Car Show — the nation’s largest and longest-running automobile exhibition (108 years!). Grab the passenger seat with your loved one and test drive one of the three indoor tracks or take advantage of the six outdoor road trials. Tickets range from $6 to $12. This is one of the finest Valentine’s Day events in Chicago for all couples.

Experience amazing views of Chicago in the Signature Room

3. Signature Room: Encounter Astonishing Views Of Chicago!

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You can take your partner to the highest clouds and enjoy beverages or even dinner at the signature room atop the Hancock building on the 95th floor. Besides the breathtaking location, the cuisine is equally delectable here. Just remember to bring your photo identification to the elevators and aim for a table upstairs.

Recommended Read: Chicago Travel Guide: Explore The Finest Sights Of The Marvelous Architectures And Scenic Landscapes!

Mix stuff in the Chopping Block

4. Chopping Block: Blend Things In The Kitchen!

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Create an unforgettable dish at The Chopping Block with your Valentine. Partner courses are available throughout the weekend, featuring festive options such as Romantic Valentine’s Dinner, Valentine’s Day Festival, Bed, and Breakfast. Attend one of these Valentine’s Day packages in Chicago classes and spend quality time with your beloved. Furthermore, every class is BYOB–you can eat, drink, and be merry. Class schedules and prices may vary.

Planning your vacation but uncertain about where to go? These travel stories assist you in finding your ultimate trip ever!

5. Riverwalk: Embark on a Romantic Stroll!

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If it is not overly cold, indulge in a leisurely promenade along the river and relish the astonishing scenery of magnificent architecture. If you intend to impress your companion with your knowledge about the various buildings along the waterfront, take a walk with the assistance of “Free tours on foot.”


Suggested Read: 9 Food Festivals In Chicago That Will Lead You Down The Path of Gastronomic Delights!

Stroll at the romantic Riverwalk

6. Magic Tricks: Prepare to be Amazed!

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Enter the Greenhouse Theatre Centre or the Uptown Underground for an early evening with the most astonishing enigma and picture masters in the city. You will enjoy mental stimulation with cabaret and traditional performances. Attend this Valentine’s Day specials in Chicago show and have some fun with your partner. Seize your main squeeze and a beverage. Unwind in awe and sit back. Or volunteer, if you dare!

Be astonished by real magic tricks

Suggested Read: 7 Delectable Chicago Food Items That You Should Definitely Try And Can Never Get Enough Of

7. Supper Cruise: An Exotic Affair!

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If you are searching for extravagant activities to do something unconventional on Valentine’s Day in Chicago, then consider this! Numerous posh, local cruise companies are prepared and await you and your sweetheart with a lunch or dinner table. But plan ahead, because reservations for Valentine’s Day (and weekend) are highly sought after, like most wining and dining spots! Would you like to celebrate your love on a day other than that of Cupid? Many dining sailings in Chicago often run throughout the year, so that you can book a different date in the meantime.

Romantic Chicago lunch or dinner cruise

8. Horse-Drawn Carriage Ride: Explore The Town!

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A carriage horse ride around the majestic mile is as poetic as it comes. Make sure to pack up and bring a blanket with your Valentine. Take a cup of steaming hot chocolate or tea while you’re riding in the winter night of the Windy City!

Suggested Read: Christmas In Chicago: Time To Celebrate Christmas Of In Mud City!

Horse-Drawn carriage ride

9. Parade: Step Out In Chinatown!

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On Valentine’s Day, Chinatown will be embracing the Monkey Year at the Lunar New Year Parade. Seek out traditional Chinese dance and music, see the streamers and cheer the “Dragon Dance.” Don’t forget to stop by a local deli to purchase pork buns, egg tarts or red bean cakes for a romantic meal.

10. Navy Pier: Take a Leisurely Stroll or a Joyride!

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Step Out for a Parade

Amble, jog, ingest, browse, frolic; everything is available at the renowned Navy Pier in Chicago’s Windy City, Illinois on Valentine’s Day. For an abundance of laughter and amusement, saunter back and forth on this internationally acclaimed gem and experience it firsthand! It may be a tad chilly, so make sure to bundle up! Prepare yourself for engaging yet pleasurable fair games with your partner. You will have a fantastic time at the Pier.

Navy Pier Walk (and ride)

Recommended Reading: 10 Popular Casinos In Chicago To Spend A Fun-Filled Holiday!

11. Field Museum: Encounter History!

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Entry is completely complimentary on Valentine’s Day for residents of Illinois. If the study of fossils captivates both of you, then this museum is the ideal choice. This venue can serve as the ultimate platform for you both to engage in intellectual conversations.

Fun at the Field Museum

12. Maggie Daley Park: Embark on a Serene Stroll!

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Your day is not complete without a leisurely walk in this park. Chicago’s scenic lake parks are perfect for your outing, but if you head north through the expansive greenway, you will discover the Cancer Survivor’s Garden in Maggie Daley Park.

The meticulously maintained garden, with its plaza and granite columns, has become one of the most highly regarded outdoor wedding venues in the city, indicating that romance is in the air. Nearby, you can ice skate with your sweetheart in the winter at the public section of the park, and during the summer, you can enjoy a game of mini-golf and indulge in a barbecue.


Recommended Reading: Weekend Getaways From Chicago: For A Fun-Packed Holiday Like Never Before!

13. Chicago Boat Tour: Set Sail!

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You’ll witness Chicago from a slightly different perspective on a Lake Michigan cruise ship. It’s also a convenient excuse to rejuvenate your love with a bottle of champagne, a delightful meal, and music in the background.

Sail away on a Chicago Boat Tour

The Odyssey and the Mystic Blue cruise ships depart and arrive multiple times a day at the Navy Pier. Choose a brunch, lunch, or dinner cruise that matches your mood and allows you ample time to explore Chicagoland together.

14. Bottle & Bottega: An Artistic Painting Class for Romance!

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Every year Bottle and Bottega organize a special class for all couples who desire to try something fresh and unleash their artistic talents. Bottle and Bottega combine a BYOB concept with a painting class center where you can spend quality time with your significant other. Prepare to create a masterpiece with your beloved while indulging in wine and delectable snacks. Isn’t wine, painting, and snacks a perfect combination for a romantic evening?

Bottle & Bottega

Location: 2900 N Lincoln Ave, Chicago, IL 60657Timings: 3 Am – 5 PmPrice: INR 2,503Website

Suggested Read: 15 Best Places To Visit In Chicago That Enhance the Charm of Your American Vacation!

15. AIRE Ancient Baths

Image SourcePrepare yourself to indulge in a luxurious bath experience with your beloved at Aire Ancient Baths. Situated in River West, Chicago, this location is ideal for couples seeking relaxation and a unique venture. It is advisable to make a reservation in advance. During one session, you will have access to 6 thermal baths including a hot bath, ice bath, warm bath, jet bath, and salt bath. Opt for a wine bath or book their Valentine’s special bath for couples, as both options are truly worth it.

AIRE Ancient Baths

Location: 800 W Superior St, Chicago, IL 60642, United StatesTimings: 9 Am – 11 PmWebsite

Further Read: 10 Incredible Indian Restaurants In Chicago To Satisfy Your Ultimate Food Cravings!

This Valentine’s Day, treat your partner to the marvels of Chicago air, its nightlife, and an unconventional celebration of cupid’s day. This to-do list will be beneficial if you wish to celebrate Valentine’s Day in Chicago. When planning your trip to Chicago in February with your loved one, experiencing these activities is almost a necessity!

Frequently Asked Questions About Valentine’s Day In Chicago

What activities can couples engage in Chicago?

There is a plethora of activities that you can explore with your significant other in Chicago such as painting classes, thermal baths, romantic dinners, and more.

Is it safe to walk in Chicago at night?

Yes, you can take a stroll in crowded areas. It is advisable to avoid dark and deserted places.

What is Chicago renowned for?

Chicago is famous for its pizza, Chicago-style hot dogs, and jazz music.

What can you do on Valentine’s Day in Chicago?

To make your loved one feel special, you can opt for a romantic dinner or attend a painting class. You can also indulge in massages or enjoy a wine bath together.

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