Spectrum
This year-old toy shop—the only one in Illinois designed for kids with special needs—is packed with sense-stimulating playthings (hammock-like swings, chewable necklaces). More interested in a baby’s day in? Have a box of staff-selected toys delivered each month through a subscription service ($45). 1911 W. Belmont Ave., spectrumtoystore.com
Present Place Chicago
With its spacious interior, elegant wooden toys, and macramé planters, this Lake View loft space is what you wish your family room could look like. “I’ve never called a play space beautiful before,” says Laura Baginski of Neighborhood Parents Network, “but this one is.” $12 for a day pass. 3701 N. Ravenswood Ave., presentplacechicago.com
Old Irving Brewing Co.
Between standout kiddie food like bacon mac and cheese and the indoor beanbag toss games, your tots might want to stay at this sunny beer hall longer than you do. Then again, a second pint of Azacca Haka pale ale sounds pretty good, doesn’t it? 4419 W. Montrose Ave., oldirvingbrewing.com
Windy City Sweets
Pixy Stix, Pop Rocks, Big League Chew, housemade s’mores—let’s be honest: For nostalgic moms and dads, bringing a child to this fantasia of a sweets shop is just a pretext. 3308 N. Broadway, windycitysweets.com
Dos Urban Cantina
The folks running this modern-Mex charmer in Logan Square just get it when it comes to kids. Each tot receives a free toy, and the children’s menu, which features creamy horchata and crispy chicken quesadillas, achieves the rare feat of being both kid-approved and authentic. 2829 W. Armitage Ave., dosurbancantina.com
CocoonCare
Perfect for moms with babies who are still in the potted-plant stage, CocoonCare’s Mommy and Me Workout ingeniously uses the weight of your tiny new gym buddy to focus on your postpartum problem areas. $25 a class, membership from $99 a month. 409 W. Huron St., cocooncare.com
Top Knot Cap from Monica + Andy
Most hats slide across little domes like clown-colored yarmulkes. Not so with this understated number, which sits low enough that you won’t have to retrieve it every 30 seconds. $13. 2038 N. Halsted St., monicaandandy.com