Written by

Agree or disagree but one thing is certain— Valentine’s Day can be a little stressful. The Valentine’s Day bar has been set quite high between selecting the perfect 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 mouldy candy hearts and corny greeting cards and create lifelong memories! Experience the attractive side of Chicago with our suggestions for the cosiest restaurants, romantic hotspots, and some wild cards!

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!

1. Sky Rink Of Peninsula: Skate Smoothly!

Be smooth at the Sky Rink of Peninsula

Image Source

Skate at the top of the world at the incredible Sky Rink of the Peninsula hotel— a rooftop rink overlooking the gorgeous Magnificent Mile in Chicago. Then cuddle in one of the ventilated lounge areas and savor 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 the at the Sky Rink is one of the most enticing things to do with your bae on Valentine's Day in Chicago in 2022.

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

Looking To Book An International Holiday?

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

Take a test ride at the Auto Show in Chicago

Image Source

Ogle over motors and fantasise about your next road trip at the Chicago Auto Show — the nation’s biggest and longest-running car show (108 years!). Grab shotgun with your dear one and take a test ride on one of the three indoor tracks or take the six outdoor test drives on the road. Tickets are available from $ 6 to $ 12. This is one of the best valentine's day events in Chicago for all couples.

3. Signature Room: Experience Amazing Views Of Chicago!

Experience amazing views of Chicago in the Signature Room

Image Source

You can take your date to the highest clouds and have beverages or even supper in the signature room at the top of the Hancock building on the 95th floor. Apart from the place being splendid, the food is quite delicious here as well. Just recollect bringing your photo identification to the lifts and aiming for a table upstairs.

Suggested Read: Chicago Travel Guide: Explore The Best Sights Of The Marvelous Architectures And Scenic Landscapes!

4. Chopping Block: Mix Stuff In The Kitchen!

Mix stuff in the Chopping Block

Image Source

Create an unforgettable dish at The Chopping Block with your Valentine. Partner courses run throughout the weekend, including festive options such as Romantic Valentine's Dinner, Valentine's Day Festival, Bed, and Breakfast. Attend one of these Valentine's Day specials in Chicago classes and spend time with your beloved. Moreover, every class is BYOB–you can eat, drink and be happy. Class times and prices vary.

Planning your holiday but confused about where to go? These travel stories help you find your best trip ever!


5. Riverwalk: Go For A Romantic Stroll!

Stroll at the romantic Riverwalk

Image Source

If it is not too chilly, take a relaxing walk along the river and savor the amazing scenery of great architecture. If you plan to charm your date with the knowledge of all the buildings along the water, take a walk with “Free tours on foot."

Suggested Read: 9 Food Festivals In Chicago That Will Take You Down The Foodies Lane!

6. Magic Tricks: Be Astonished!

Be astonished by real magic tricks

Image Source

Enter the Greenhouse Theatre Centre or the Uptown Underground for an early evening with the most astonishing mystery and image masters in the city. You will relish cognitive titillation with cabaret and old-fashioned performances. Attend this Valentine's Day specials in Chicago show and have some fun with your partner. Grab your main squeeze and a drink. Relax in wonderment and sit back. Or volunteer, if you dare!

Suggested Read: 7 Lip Smacking Chicago Food Items That You Should Definitely Try And Can Never Have Enough Of

7. Dinner Cruise: An Exotic Affair!

Romantic Chicago lunch or dinner cruise

Image Source

If you are seeking opulent things to do something outside the box on Valentine's Day in Chicago, then consider this! A number of swanky, local cruise companies are prepared and wait for you and your heartthrob with a lunch or dinner table. But think ahead, because bookings for Valentine's Day (and weekend) are a big seller, like most wine 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 interim.

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

Horse-Drawn carriage ride

Image Source

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 cacao 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!

9. Parade: Step Out In Chinatown!

Step Out for a Parade

Image Source

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

10. Navy Pier: Go For A Walk Or A Ride!

Navy Pier Walk (and ride)

Image Source

Stroll, run, consume, shop, play; everything's on the celebrated Navy Pier in Chicago's Windy City, Illinois on Valentine’s Day. For plenty of laughs and sport, take a walk up and down this world-renowned beauty and experience it for yourself! It could certainly be a bit chilly, so bundle up! Get ready to play demanding but enjoyable carnival matches with your spouse. You're going to have a blast at the Pier.

Suggested Read: 10 Popular Casinos In Chicago To Spend A Fun-Filled Holiday!

11. Field Museum: Have An Encounter With History!

Fun at the Field Museum

Image Source

The entry here is entirely free on Valentine's Day for Illinois residents. If paleontology fascinates you both, then this museum is the one for you. This place can be an ultimate platform for you both to have intellectual discussions.

12. Maggie Daley Park: Go On A Relaxing Stroll!


Image Source

Your day isn’t over if you haven’t had a relaxed stroll in this park. Chicago's picturesque lake parks are ideal for your excursion but you'll find the Cancer Survivor’s Garden in Maggie Daley Park if you slip north most of the vast greenway.

The perfectly tended garden with its plaza and granite columns has become one of the top-ranked open-air marriage spots in the city, so you know that courtship is in the air. Nearby you can skate with your sweetheart in the winter in the public part of the park and play mini-golf and barbecue in the summertime.

Suggested Read: Weekend Getaways From Chicago: For A Fun-Packed Holiday Like Never Before!

13. Chicago Boat Tour: Sail Away!

Sail away on a Chicago Boat Tour

Image Source

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

The Odyssey and the Mystic Blue cruise ships leave and return with many sails a day to the Navy Pier. Select a brunch, lunch or dinner cruise that suits your tone and gives you plenty of time to go to Chicagoland together.

14. Bottle & Bottega: A Romantic Painting Class!

Bottle & Bottega

Image Source

Every year Bottle and Bottega organize a special class for all couples who want to try something new and explore their artistic side. Bottle and Bottega are a mix of BYOB and painting class center where you can spend time with bae. Get ready to create a masterpiece with your beloved while enjoying wine and delicious snacks. Isn’t wine, painting, and snacks a perfect combo for a romantic evening?’

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

Suggested Read: 15 Best Places To Visit In Chicago That Add Charm To Your American Vacay!

15. AIRE Ancient Baths

AIRE Ancient Baths

Image Source
Get prepared to enjoy an exotic bath with your beloved at Aire Ancient Baths. Located in River West, Chicago, this spot is perfect for couples who want to relax and try something new. You should make your reservation beforehand. In one session you will have access to 6 thermal baths that are hot bath, ice bath, warm bath, jet bath,  and salt bath. Go for a wine bath or book their Valentine’s special bath for couples, as both are worth it.

Location: 800 W Superior St, Chicago, IL 60642, United States
Timings: 9 Am – 11 Pm

Further Read: 10 Amazing Indian Restaurants In Chicago For An Ultimate Foodgasm!

This valentine’s day, treat your lover to the wonders of Chicago air, its nightlife and an unorthodox celebration of cupid’s day. This to-do list will be helpful to you if you want to celebrate Valentines Day in Chicago. While planning your trip to Chicago during February with your loved one, experiencing these things is almost a must!

Frequently Asked Questions About Valentine’s Day In Chicago

What can couples do in Chicago?

There are a plethora of activities that you can try with your beloved in Chicago like painting classes, thermal baths, romantic dinners and more.

Is Chicago safe to walk at night?

Yes, you can go for a walk in places that are crowded. You should avoid places that are dark and not crowded.

What is Chicago known for?

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

What is there to do on Valentine’s Day in Chicago?

To make your beloved feel special you can go for a romantic dinner or go to a painting class. You can also enjoy massages or take a wine bath together.

Looking To Book A Holiday Package?

Category: Chicago, Things To Do, USA

Best Places To Visit In India By Month

Best Places To Visit Outside India By Month