Party Hearty! Best Ways to Spend Valentine’s Day Weekend as a Family

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Celebrate the sweetest holiday of the year, family-style, with craft workshops, meals and parties bursting with creativity across town. Read on to find the events and special offerings we’re totally crushing on this Valentine’s Day.


Peek at Fanciful Fish in Greektown

Take the family to stroll along Halsted Street in Greektown to view the Fanciful Fish outdoor sculpture exhibit. Through April, you'll find 21 artworks created by a diverse group of Chicago artists celebrating Greek culture: from mythological gods and seaside vistas to the Green language.

photo: iStock

Check Out Chicago Children's Theatre's Walkie Talkies

Chicago Children's Theatre got creative during COVID shutdowns! They commissioned fun, totally original audio experiences that facilitate families exploring Chicago neighborhoods. Using Walkie Talkies, take a self-guided tour through South Shore, Little Village and around the North Pond Nature Sanctuary in Lincoln Park. Even on a chilly February weekend, you can be outside learning about the beautiful city we call home. 

Have a Scavenger-Hunting Adventure

Show your kids the coolness of their hometown with a scavenger hunt. You'll spy on Navy Pier's Ferris Wheel and stroll along the Chicago River to see its moveable bridges. Best part? You can do all this in a totally safe, socially distanced way that’ll keep Covid-19 far, far away. Mask up and hop in the car to seek out these Insta-worthy Chicago landmarks. You can download our Chicago-themed scavenger hunt for kids here.

photo: 360 CHICAGO

Put Your Heads in the Clouds at 360 CHICAGO & Tilt

Visit the newly reopened 360 CHICAGO Observation Deck for expansive views of the city and surrounding states. 

Visit a Museum

Chicago has some of the best children’s museums in the world where interactive play, with a focus on engaging youth development, is the modus operandi. All have been closed for months, but with new COVID-19 protocols in place, some have expanded their offerings to slowly allow in-person visits.


Bundle Up for a Wintry Hike

Sure, a Chicago winter is brutal. But, COVID has made us realize we're willing to battle the elements and eat our dinner outside if we have to. So, we know you're up for a hike. Get a dose of fresh air, unforgettable scenery and a chance to visit animals in their natural habitats. There are beautiful trails all around the city that'll have you lacing up your boots, strapping an infant to your back and setting out for an adventure. 

See Eagles at Starved Rock State Park

Winter, spring, summer or fall, all you have to do is haul your crew to Starved Rock State Park for hiking with a stellar view. Starting in mid-January, thousands of eagles migrate to Starved Rock State Park and stay through March. They’re easy to spot as they soar through the sky or perch on the treetops. Take binoculars!

Walk the Grounds at Chicago Botanic Garden

Even when it's cold outside, there is plenty to see, do, touch, taste, hear and explore at Chicago Botanic Garden. The peaceful allure of nature in winter reminds us to appreciate the simple pleasures of the season. Unwind on a walk through the quiet solitude and reap fresh air benefits. Bring binoculars to catch a glimpse of feathered friends and don't forget your camera to capture unexpected beauty.


Take a Spin at Maggie Daley Park

The Maggie Daley Park ice skating ribbon is one of the best spots in the city to skate a figure eight. The railing that lines the loop is the perfect pick-me-up for wobbly skaters. 

photo: iStock

Lace Up & Head to The Forge

It wouldn't be a midwest winter without ice skating on the to-do menu. Lace-up your skates—or rent a pair—and glide across The Forge's Ice Skating Shelf. Teleport yourself to childhood memories and create new moments to cherish.


Borrow Some Fun from DuPage Children’s Museum

No reopening date has been announced for DuPage Children's Museum, but you can bring the museum to you! If you're missing DCM, turn your home into a hands-on museum by having portable exhibits delivered right to your doorstep.

photo: iStock

Bake & Cook with The Kids' Table

Work side-by-side with your kids in virtual classes to make delicious heart-shaped cookies, a flourless chocolate cake or a Valentine's dinner with the help of The Kids' Table. It's the perfect fun-filled family activity with hands-on instruction and recipes you can recreate later. 


Find a New Favorite Neighborhood Toy Store

Valentine's Day is the perfect reason to get your kids a just-because gift. Make your kid's toy-filled dreams come true at a locally owned toy store

Hunt for Chicago's Best Cup of Hot Cocoa

Make this winter weekend a little easier to swallow with a steaming cup of hot chocolate. When Jack Frost comes nipping at your nose, it’s time to go sipping. If your kids love cocoa—or need a good introduction to it—check out local restaurants or cafes that make their own from scratch. 

Intro Your Kids to a Chicago Hot Dog

Love ’em or leave ’em, hot dogs are big in Chicago, and if your kids haven’t begged for one yet, they will soon. We love the on-the-go ease (no silverware!) and colorful condiments (kids get a pass where the sacrilege of using ketchup is concerned). Grab one at a legendary local hot dog spot and turn eating into an adventure. 

Fill Your Bellies with a Hearty Bowl of Soup

Slurp it. Stir it. Make waves. Blow on it. Nibble the good stuff and use a straw for the rest. No wonder kids love soup; it’s so fun to eat. And it keeps us warm and cozy, which right now is a very good thing. From a Jewish deli with great Matzah balls to an Argyle Street pho haven, we'll help you get your fix by sharing our favorite Chicago restaurants for soup. 



photo: Wilmot Mountain

Hit the Slopes in Wilmot Mountain in Wisconsin

Pack your snow gear and head about an hour north of Chicago to Wilmot Mountain for snowboarding, skiing and tubing. Wilmot has been in operation since 1938, but with their recent facelift, skiers and boarders can now enjoy updated towers and chairs, rope tows, an expanded terrain park, beginner area conveyor lifts, new decor in the base lodge and improved dining options. 

Find a Cozy Cabin

For a change of scenery or maybe even a quick getaway without the kids, escape to a sweet cabin in the woods. Within a short drive, you'll find cozy cabins, sweet cottages and even a converted grain bin to unplug and schedule time amongst the trees and alongside lakes. Relax, unwind and say hey to Mother Nature. Find your retreat here