Our Playdate series is popping up in Chicago! If you're joining us and looking to explore the city we've rounded up some of our fave kid-friendly, Tubby Todd mama-approved spots to visit! Check 'em out below.
🌳 Best for a Park Play Date
● Maggie Daley Park – Iconic downtown playground with climbing walls, mini-golf, and splash pads
● Sauganash Park – A quieter spot with swings and shaded areas perfect for picnics
● 606 Bike Path- New playground right at the exit of the trail
● Holstein Park- Splash pad perfect for summer days
☕ Coffee Spots for a Quick Pick-Me-Up
● Dayglow Coffee (right off of 606)
● Heritage Bikes & Coffee – Sip while your kiddo checks out the custom bikes
🍦 Sweet Treats + Ice Cream
● Margie's Candies – Old-school sundaes and handmade chocolates
● Pretty Cool Ice Cream – Creative flavors and kid-friendly bars with dairy-free options.
● Sweet Mandy B’s - Any sweet treat a kiddo can dream of and perfect for custom cake and cookie design
● Scooters Custard- Line out the door on sumer nights and always worth the wait!
● Miko’s Italian Ice- Best Italian Ice in the city!
🧸 Stuffie Shopping Adventures
● Timeless Toys – Classic and modern toys with a fantastic stuffed animal section
● Rotofugi – Quirky collectibles and plush characters in a fun gallery space
● Play - Logan Square locally owned favorite
● The Red Balloon Co - perfect for last minute birthday gifts!
🧘 When Mama Has the Day Off
● AIRE Ancient Baths – Tranquil oasis in the West Loop for ultimate relaxation
● The Peninsula Spa – Luxe spa day with skyline views and serene pools
● Walk down Damen – Coffee at Ipsento, vintage shops, and dreamy home boutiques
● West Loop – Lunch at Beatrix or Aba followed by a shopping stroll on Randolph and afternoon coffee at Sawada
● Scratch Goods for DIY facial
● Solo glass of wine and people watching at Webster Wine Bar
● Nobu rooftop for small bites and beautiful views
🎨 Zoos + Museums
● Lincoln Park Zoo – Free and centrally located with a great children’s area
● Brookfield Zoo – Huge and immersive, perfect for a full-day outing
● Museum of Science & Industry – Interactive exhibits, great for all ages
● Chicago Children’s Museum – Full of sensory fun, located on Navy Pier
● Adler Planetarium – Space-themed exhibits and skyline views
⚾ Baseball & Family Vibes
● Cubs Game at Wrigley Field – Grab a dog, catch a few innings
● Gallagher Way – Grassy area outside Wrigley with splash pads, movies, and kid-friendly events
🍽️ Best Kid-Friendly Restaurants
● Parson’s Chicken & Fish – Patios, nuggets, and frozen treats
● Crosby’s Kitchen – Comfort food, cozy booths, and a kids' menu
● The Warbler – Spacious, shareable dishes in Lincoln Square
● Tuco & Blondie – Colorful, festive, and kids eat free
● Mott Street – Patio dining with globally inspired comfort food
● Paradise Park – Pizza and outdoor vibes that entertain everyone
● Middlebrow Pizza - Outside space to hang and play
● Lou Malnati’s - Classic chicago deep dish and spacious for kids to wander
🎶 Music for Minis (and Parents)
● Old Town School of Folk Music – Live shows and music classes
● Chicago Symphony Family Matinees – Introduce your littles to the classics
● Ravinia Festival – Summer concerts with room to dance and picnic
● Rock N Roll Playhouse live Music
🎉 Family Festivals & Street Fairs
● West Fest – Live music, Kid Fest, and a real neighborhood feel
● Wicker Park Fest – Artsy, energetic, and surprisingly family-friendly
💃 Move, Mama, Move!
● Pilates + Coffee in Roscoe Village – Flow at Lateral Fitness then recharge at Pilates + Coffee
● Lakefront Run – Lace up for stroller runs or solo jogs by the lake
● Yoga in the Park – Check local listings for weekend pop-ups
🚲 Boats & Bikes
● Divvy Bikes – Rent from kiosks across the city, including the lakefront trail
● Chicago Electric Boat Company – Cruise the Chicago River with the fam
● Urban Kayaks – For adventurous mamas and water-loving kiddos!
