As I just repatriated from the Windy City (as did a few of my Shorewood peeps), I have a few tips if you're trying to have a fun "HEy, Let's go to CHICAGO!" kind of Spring Break Day. I assure you, it can quickly become unfun, so being prepared will ensure that you, the parent, the one with the bright idea in the first place, yes you, that you don't unravel and just yell at the kids and start worrying as soon as you get there about missing the train home. I, personally, would feel somehow responsible. If you do find yourself standing somewhere in that city, there are numbers to call for help. You can email me directly and I'll try to help you. That's how much I care about my fellow Shorewoodians. I know, you're just trying to spice it up a little, not dice it up. So email me.
But hopefully by reading this you won't have to do that, you'll be too busy!
As I mentioned, First, gather information about the city. Second, plan the lesson, in a way. Size up your travel companions. Can each of them walk a mile? If not, skip the train. If so, consider it. In planning the lesson, think about what you'd like them to learn on this trip to Chicago. A good trip to Chicago can build navigation skills, an understanding and moderate competence with different forms of transportation, city smarts, a little wow, a little ooh and ahhh, and at least one "Mom, this is the COOLest" no matter what age. Is this going to end up being a slog from store to store with expensive food in between? No. You want to see grocery stores that sell live octopus. You want to see real second hand stores if you're with a teen, and not dept. stores on Michigan Ave. (The Macy's for example on State has MUCH better options for anyone under 82, except if you're going to charge a bottle of wine to enjoy on the train and your Macy's card is the only one (because it used to be a Marshall Fields charge) that has any credit left on it after a big day, they do have an easily accessible wine and chocolate stop right there at the Mich Ave store in Water Tower).
Getting off the train, or driving in to the city, is not like going to Disneyworld. No one will greet you with brochures, and there aren't big signs over the areas for "FOOD" "Fun RIDES" "RESTROOMS". You are going to need to be armed with a few backstage-passes-to-clever in order to steward your group to a worry-free time. I'm going to give 'em to ya.
For the Trip for someone with multiple kids and at least one stroller: you'll want to head to the land of Burleys and Gracos and people like you first. It will be nicer, and you'll be more in control. That means Lakeview. So, Drive. If you have a ratio of one adult per child under 14, or you are with tweens who have demonstrated competence in not making you crazy, take the train. With Ipods, you'll have four hours less with them really, so that might be handy? Remember, Union Station is in the middle of nowhere (assuming that you are not going in to work, and have kids along). That said, it is a rush in itself to come up to street level during rush hour, which there is a Koyaniskatsi-esque snake of people rushing and clanging to work over bridges over the river, which is a memory I hold dear of one of my first trips to Chicago. You have to be an early bird to catch it though. Otherwise, unless the Sears Tower or the Board of Trade are on your list, think hard about it. It is not near Michigan Ave, or the Lake, or any museums or anything remotely pleasant to look at really. You'll come out expecting Michigan Avenue and will have to hail a scruddy cab or wait for a bus to take you up to the Gold Coast or over to State Street to the Marshall Fields/Macy's building. The train isn't cheap, the MegaBus is a great deal but schtinky, and both land you at Union Station.
Park in the Trader Joe's lot on Lincoln and Grace. Go there, and go to the CB2 right next to it.
Lincoln Square is Kid Friendly though it will be a shopping trip, it will be a walking and el-taking shopping trip with kid-friendly restaurants and toy stores and things for tweens too.
If you don't have a stroller, you could take a nice walk (it starts not to pretty but it's totally safe) to the El at Irving or Addison, ride to Western and go to Lincoln Square. My new friend P. didn't even know each other when we lived in Chicago but each loved going to Cafe Selmarie and letting the kids run around the little stage area and square that is next to the cafe. I personally have friends who work at the Sulzer library, which is a great resource if you live there but novel only in the vertigo-inducing stairs up to the second floor. The cafe Grind is hipper for the harder-to-impress than Selmarie. There is a Mertz Apothecary, the store Enjoy, a German grocery store, German restaurant, and movie theater. More restaurants a little further down. Now that there is no smoking in Chicago, it's all really nice. Some of those places used to be intensely smoky,..now not at all! If you walk all the way down from Lawrence to Montrose on Lincoln, past the library, you'll come to the Golden Angel. I spent a lot of nights hanging out there with Steve. I'd work late at the art studio, he'd work crazy late at work, and we'd meet there for soup and coffee at 11pm - he'd take the train and I'd drive our old Trooper that looked a spittin image like the Beverly Hillbillies car. Having seen it during the day recently, I think nighttime is the right time for that place. BUT further down Lincoln there's Jury's (where Steve proposed and also has great burgers) (and you can walk down Lincoln and start to come into other neighborhoods - it only gets better from Lawrence...then boom .. you're back at your car!).
The two El stops on the North Side that are wheelchair (e.g. Stroller) accessible are Western and Merchandise Mart.