The Windy City

Second that. Just a great place. And KC, I think you will find that the best view of the Chicago skyline from ground level will come from the aquarium. Great photo op location.

 

Notes from a native (or, at least a guy who has lived in the area for 10 years now):

1. http://www.metrarail.com -- This will get you train schedules. If you're going on a weekday, look for the Heritage Corridor -- Lockport will be your closest stop. On a weekend -- or even on a weekday, given the frequency of trains -- look at the Rock Island line. You would pick up the train at Union Station in Joliet, which is not that far away. If I were you, I would take the train in whenever possible. You can always cab it from place to place, though the downside of that would be the lack of carseat for your 14-month-old. But you won't be far from the Museum Campus or Navy Pier. Believe me, what you'll spend in cabs will be less than you'll spend in parking.

2. Speaking of Joliet, you won't be that far from Silver Cross Field, home to the Northern League's Joliet JackHammers. A very good minor-league ballpark, and it has a kids' play area as well. http://jackhammerbaseball.com/

3. If you go to Sox Park (say it like a native!), buy lower-level seats if you want your kids to be able to take advantage of the kids' deck in left field. Thanks to Ligues, if you buy upper-level seats, you have to stay there. Just buy the cheapest lower-level tickets you can, and enjoy the walk around the park (plenty of elbow room in the concourses) and the kids' stuff. Unfortunately, you will have to drive here -- no Metra stop at Sox Park. Take 55 all the way in, get off at the Ryan heading to Indiana, then go south until 31st Street.

4. After (or before) the game, you can head to Chinatown (whose borders have bled closer to Sox Park over the years), or go just outside of Chinatown to the original location of Connie's Pizza, a spot I'd highly recommend (it's on Archer Avenue -- easy to get to from Sox Park). Also, feel free and easy to walk around Bridgeport. It's gentrified quite a bit, although maybe I'm comfortable because some of my wife's family is from there, and I've been there plenty of times, including taking my oldest son to a birthday party at a church that included two gyms, video games and a bowling alley. A great place to get snowed in, that's for sure.

5. If you're in Romeoville, tour the National Weather Service office!

 

There is nothing more stunningly scenic than the oases (plural?) on the Tri-State.

If you want to do a (theoretically) short roadie from Chicago, check out the Indiana Dunes State Park. Kinda cool.

 

Or go to Great Lakes Naval Training Center, where my grandpa was the baddest drill instructor around. At least that's what pops said.

 

Don't forget about Chicago-style hot dogs.

 

Which, ideally, should be kosher and eaten with celery salt.

 

AND NO KETCHUP!!!!!

Which reminds me, avoid tourist-trap restaurants like Ed Debevic's and the Billy Goat (yeah, I said it) at all costs.

 

Yeah, we'd love to get some real Chicago dogs. Once I was eating lunch in college with a buddy, and we went to go get the hot dog lunch. I put ketchup on mine, and he being a Chicago native, he about beat the piss out of me. He chewed me out the entire time we ate.

"You do NOT put ketchup on your hot dog!"

Haven't put ketchup on my hot dogs since.

 

I usually get mustard, onions and celery salt (don't like tomatoes or relish). At Wrigley, I eat them plain.

 

Ah, celery salt.

 

Ed Debevics isn't the worst idea for kids who are 8, 4 and 14 months...it's loud, and you can get milkshakes.

A block away you can get the same stuff at the Rock and Roll McDonalds, but the people can be somewhat gross.

As for the hot dogs, not worth haul with the kids, but there is none better than the Weiner's Circle, especially at at 4 am.

 

For the same thing, you're better off at Portillo's, which across the street from the huge-ass Rock 'n' Roll McDonald's. Portillo's is a chain, but at least it's local. And the kids will love all the stuff they've got hanging all over the place, including a 1930s car. Or you can go to the Rainforest Cafe, another block away.

Around the same area you can get on various tour buses, including a black school bus for the Al Capone-ish tour. It makes one wonder whether, in 50 years, there will be buses for a Latin Kings or Vice Lords tour.