D.K.
Hi M.,
Totally been there. My kids are so far apart, each is like an only child. My big guy is 19, daughter is 10 and baby is 21 mos! When my oldest was still home, Family Day was a challenge. Every Sunday we do something all together, after church. It is just understood that you don't make plans. period. That said, it was up to us to make sure we did something together and tried to make everyone happy. Some weeks were better than others. Here's my take on your dilemma...
Cantigny is fun for boys of all ages. It's in Winfield at the intersection of Winfield & Roosevelt Roads. There's a First Infantry Museum and tanks they can climb on. There's a cool park, pretty gardens for a stroll, you can tour the old McCormack mansion and it only costs $5 to park. Bring a picnic make a day of it.
Museums are good for everyone, we all have something to learn. The Field Museum rocks the house with the dino exhibits for the little guy and other guys might have fun helping their brother learn and will totally get points from girls for being smart about cultural stuff and good to their bro. :) That helped a lot with my big guy when the baby came along. He really had fun showing him stuff. Still does when he is home on leave. The Shedd Aquarium is excellent as is the Musuem of Science and Industry.
Go for a hike at a forest preserve, depending upon where you live there are some great ones around. Up north there is a really neat one called Volo Bog, come to think of it there's a car museum up there, too. That'd be really great for a bunch of guys.
Check out Enjoyillinois.com It's chock full of things to do. Make a big day trip out to Starved Rock. Go canoeing on the Fox River outside of Ottawa. The little guy could do that and boy is it fun to rough-house on the river when you're a teenager! My family did that many years when I was growing up. Be sure to bring coolers full of drinks & sandwiches, snacks, it takes longer than you'd think, but is totally fun! And definitely don't forget the sun block.
Pack a picnic and go to the beach, have a walking tour of Chicago! Play tourist in our town, we live in one of the best towns around! Having lived here most of my life, then moved away while in the Air Force, I sure missed the cultural draw here. There's always something to do or different foods to eat. We are spoiled. Teach your boys all this and they'll be great dates then husbands & dads.
Obviously some of these things are more expensive than others, so pace yourself, but have FUN! Those boys will be grown and gone before you know it and you'll be so happy you took the time and invested it well. They're fertile soil and will soak up the adventure and even some of the culture, though they'll fuss while they're "enduring" it! lol.
D.