Whether your son is 5 or 15, one-on-one time matters and Chicago offers endless ways to make it fun.
We gathered ideas that combine conversation, creativity and a bit of adventure, perfect for every season. Each one is family-friendly, easy to plan and guaranteed to bring smiles (and maybe a few selfies).
Build your own pizza night at Home Run Inn
Turn dinner into an activity by heading to this beloved Chicago pizza spot, where you can share, laugh and customize toppings together. Make it a challenge: who builds the best pizza? The relaxed atmosphere makes it perfect for younger kids, while older boys love sampling Chicago-style slices. End the night with a root beer toast and take leftovers home for the rest of the family.
- Address: 4254 W. 31st St., Chicago
- Hours: 11 a.m.–9 p.m. Monday-Thursday; 11 a.m.–10 p.m. Friday-Saturday; 11 a.m.–9 p.m. Sunday
- Phone: (773) 247-9696
Go retro at Galloping Ghost Arcade
If your son loves gaming, Galloping Ghost Arcade in Brookfield is an unforgettable night out. It’s the largest arcade in the U.S., with more than 850 machines from Pac-Man to Mortal Kombat. The all-day pass gives you unlimited plays, so there’s no need to count quarters. Compete for the high score or team up to beat old-school classics together.
- Address: 9415 Ogden Ave., Brookfield
- Hours: 11 a.m.–midnight Monday-Thursday; 11 a.m.–2 a.m. Friday-Saturday; 11 a.m.–midnight Sunday
- Phone: (708) 485-4700
Try glow-in-the-dark mini golf at Space Golf
For something playful and out of this world, Space Golf in Orland Park brings intergalactic fun to your night out. The neon planets, glowing aliens and blacklight course make every hole feel like a sci-fi adventure. Kids love the theme, and parents love that it’s indoors, perfect for winter or rainy days. End the evening with hot cocoa nearby.
- Address: 15611 S. 94th Ave., Orland Park
- Hours: 4–10 p.m. Monday and Thursday; 4–11 p.m. Friday; 12–11 p.m. Saturday; noon–8 p.m. Sunday
- Phone: (708) 460-3887
Catch a game at Wrigley Field or United Center
Few things bring moms and sons together like cheering for a team. Whether it’s summer baseball with the Cubs at Wrigley Field or winter basketball with the Bulls at United Center, game nights make lasting memories. Grab a jersey, snap a selfie and let your son pick the snacks: nachos, popcorn and soft pretzels always win.
Wrigley Field
- Address: 1060 W. Addison St., Chicago
- Phone: (800) 843-2827
United Center
- Address: 1901 W Madison St., Chicago
- Phone: (312) 455-4500
Make it your tradition
The best part about mother-son date nights isn’t where you go, it’s the time you share. Rotate your activities, let your son choose the next outing or plan one monthly. Whether it’s a pizza slice, an arcade battle or cheering in the stands, these Chicago adventures make bonding easy and fun for both of you.
